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March 4, 2019 by Wall Street Playboys 52 Comments

Dressing Sharp: Ignore What People Say, Go By The Results

Dressing Sharp: Ignore What People Say, Go By The Results

Once in a while we have to cut out the frugal people who accidentally come here and believe we’re in the same group (not even close). Frugal people believe in scarcity which is why they focus on cost cutting even though there is a significant floor to cost cutting. No matter how much you try and reduce your expenses, you will still spend money. We’re going to walk through the escalation of spending and how becoming a millionaire to eat lentils, beans and rice is equivalent to getting in shape to develop a heroin addiction (defeating the purpose entirely). The progression and lifestyle changes will be covered in our book coming out later in the year to complete the trilogy but this should be a good way to think about the future. 

The Five Most Common Arguments

“I Wouldn’t Buy That”: This is the starting point for all the excuses. People who don’t have money claim that no one cares about brand name goods, higher end apartments, nice cars etc. Back when we had no money, using mild salsa and draining it to get vegetable intake for the week, this was a common argument “I would never buy that if I was rich”. The reality? This was an obvious sign of scarcity belief systems. Anyone who eventually makes it knows that the quality of the goods certainly makes a difference. With many things in life, after you get to certain net worth and income level (described in our book) you’ll actually *lose* money by trying to act like you’re still broke. People have mistaken our comment about “stealth wealth” to mean that you should dress in $9 H&M t-shirts. This couldn’t be more wrong. Stealth wealth means you’re not famous but people know you are not struggling for cash. This is the right balance.

“No One Knows the Difference”: This one is just unbelievable. There are studies that say regular people cannot tell the difference between shoes. There are also studies that say “women don’t like muscular men”. Since they are incredibly wrong, we have to highlight them. Unless you’re born under a rock you know for sure that by being muscular and in shape you will certainly have more dating opportunities in any environment where you will be shirtless (the beach, outdoors playing sports etc.). There is just no argument here and studies don’t work since a “study” is based on what people say not what they do. Making decisions based on what people say would result in failed decisions for life. It’s similar to pornography and racism. Everyone “says” they don’t watch porn but it’s the highest traffic industry. People “say” that racism exists but then you ask people to raise their hand if they are racist… crickets. These are two clear as day examples to prove that going by what people “say” is a disaster. Bonus: people also say they “don’t click ads” on the internet. Then how come the ad companies make billions of dollars. 

“On Credit”: This is the third most common excuse. People claim that luxury brands are for broke people buying on credit. Also not true. The Luxury market is primarily dominated by international travelers (this of course makes sense as frequent international travelers are unlikely broke). While it is true that many people go into debt status chasing (not something we recommend since that’s hilarious), the largest buyers are actually rich. The large buyers do not buy “just one” unit of anything. They typically have a set of items they rotate at minimum. When you go to a high end place frequently, instead of assuming people there are only “flexing” for the day… wait and see if they come back. If they come back several times and always have different nice items on… They are rich and there is no need to hate on it.

“I Don’t Like Fancy Clothing”: This one is just as bad as the “studies” excuse. It is easy to take down. Anyone reading this right now can go ahead and prove that it makes a difference. Go through your entire wardrobe and put on the nicest stuff you have. Do not lie. Everyone and their mom has a “nice outfit” for going out, weddings, special events etc. Now after you’ve put on the best outfit you’ve got, ask yourself if you feel better/more confident/more important. Use any positive attribute. Unless you’re afraid of becoming rich or you’re lying to yourself… you know you feel like ten million bucks. Since it changes the way you feel and think this naturally works.

“Not Worth It”: The final item sets in. It “isn’t worth it”. Sure. If you want to live a boring life, it isn’t worth it. That is for sure. It means that getting rich in the first place was a total waste of time. If you want to get rich to walk around in $5 t-shirts and drive a Honda Civic to your $150,000 home in the suburbs… you should have retired years ago! If it really wasn’t worth it and it really wasn’t something you envisioned having… then the person also wouldn’t have the need to comment on it. It’s always the people that are the most jealous that will comment on it. Same story. Every time. 

The Five Most Common Mistakes

I Bought XX and It Didn’t Work: The beautiful thing about being well dressed is you *don’t* need the highest brands at all times and you *don’t* need to go directly to the top end. This is the truth. It takes several years to develop your own style that gets the best reactions based on your personality, your skin tone, body type and the venues you go to. If you’re going out in Vegas/Miami your ideal “look” is not going to match the guy going out in New York or London. There are different vibes for each city and the city you like naturally has a specific personality trait as well. This is the most common mistake. People think they can just “buy some brand” and have it work. That’s not how style operates. 

The most common one we’ve seen is when people get their first high paying career/business going. They always do the same thing. They cut corners on spending (food/dry cleaning etc.). They save save save… Then they buy some Ferragamo/Gucci loafers and entry level luxury watch. This is so common it honestly hurts typing out. This is sending the *wrong* message. The message being sent is that you’re trying to get attention because you have one or two items that are “high-end”. Even worse is when the shoes don’t match the clothing which happens pretty much 99% of the time. Again. If the clothing color and style doesn’t match, no one is going to care about the brand because “something is wrong” and everyone knows it. You’re trying to impress people and that’s never a good thing. 

Not Congruent: Everything needs to be in the same region. What does this mean? It means that you shouldn’t be carrying a $5 plastic wallet if your suit is worth $1,000. It doesn’t look right. Similar to the section above where the shoe style or colors don’t line up, the general categories need to be in the same region. You’re allowed to have 2 items at most that are not in-line. By way of example, if your cufflinks are $30 and your socks are only worth $5… no one is going to notice or care. In fact, a couple small items that are cheaper typically have a “story” to them hence why you’re wearing it. To take it to the other extreme, being incongruent is like going into a Chipotle with a custom made suit and Gucci Oxfords on… That image is quite painful as well. 

Have to Get All Clothing on Sale: Stopping here for a second. The main reason why you’re learning to look good/dress well and know the right brands is to attract the type of women you actually want to date. Stop and ask yourself “Would this type of girl date this type of guy”. Be honest. Anyone who really believes that an *attractive* woman would choose a fat slob with $100M over a well dressed in shape muscular guy with $10M… is clearly insane. If the girl would actually choose the $100M person, it means she’s likely for sale (you either see it and notice it or you don’t). 

Now back to the point, the most common mistake is trying to do everything in the same range at once. This is not necessary. If you’re going to go out to a normal venue where you suspect you won’t see a single suit… Don’t wear the high end stuff and leave it all at home. You’re probably going to wear something more fitting like a high end pair of jeans, a basic blazer and even a regular t-shirt. The goal is to stand out in a positive way that matches the actual environment. Over time as you get wealthier and wealthier you’re not going to have a “versatile” wardrobe and it’ll evolve into the higher end in general anyway. No need to buy stuff you aren’t going to use. If you plan on going to a nice place 1-2x a month, you need 1-2 upper tier shoes. If you are going to go every single day…. Well then yes the upgrade is needed.

Upgrading Where it’s Meaningless: We’re sure there is some angle here, but at the end of the day, upgrading wardrobes being used for outdoor activities or the gym are low ROI. Here you can go ahead and buy those basic shirts and shorts (nike, adidas, it doesn’t matter) and use that for the gym. If you’re smart, you’re already in a high end gym so that’s the “entry price”. As long as you’re not walking around in shirts/shoes that are 5 years old, you really don’t need to have anything special. Also. If you do end up going to a nicer gym you’ll notice that the attractive girls always have nice gym outfits as well. This is just how it works. The more attractive they are the more focused they are on their appearance which means they are on their “A game” even at the gym.

Another meaningless upgrade is actually work! That’s right. If you’re still grinding it out at work and there are no clients that day, there is no real reason to wear anything brand oriented. Those shoes and shirts are going to get more wear and tear on them and you can simply chuck them at the end. Your higher quality items are for 1) meetings, 2) events and 3) higher end venues. Since everyone wants to know the exact formula we’ll use examples: 1) meetings would be anything that is going to generate you money, 2) events would be any event where you’re going to meet someone of importance and 3) higher end venues would be a place like Catch on a Monday in NYC, the Wynn/Encore at Vegas or a Michelin Star Restaurant. If you have a rough weekend coming up with long hours of work, you should just use some of your “throwaway clothing”, items you wear to normal days at work or to a regular lunch spot/bar. 

Overspending: If you’ve found this blog we’ll guarantee that this will occur when you first attempt to adjust your wardrobe and style. Why? Well if you already followed our basic style advice from Efficiency you’ll already know it works (we already got numerous emails about dates/promotions attributed to looking professional/sharp). Since you know it works, you’re going to have to go up the learning curve and will likely overspend up front to figure it out. The only way to prevent this is to sit, stop and think about the type of people you’re trying to attract. The more you can target your audience (i.e. Facebook ads!), the better the results! On a serious note since the prior paragraphs make it seem like the changes need to be made today, you have to know what you’re going to do.

That last part needs to be read a hundred times. Unless you know the type of places you like, the cities you’re going to go to and the people you enjoy being around… Tailoring specifically to your audience isn’t going to work and you’ll blow up. Tying this back to Ferragamo loafers (classic style error), they *do* work for people who typically operate in jeans and drive a lot. They *don’t* work for guys who like to dress in custom suits and drink champagne (the shoes need to be flipped to oxfords or double monks for example). There are small nuances like this. Ferragamo shoes are great for the right venue and are not great for the wrong venue (just like every other brand on the planet). 

The second part of emphasis here is finding the “light version”. If you’re not sure who you want to be yet, or what venues you’ll go to… there is always a starter brand. If you look at the design of the upper mid range: To Boot New York, Magnanni, Allen Edmonds and almost anything else found at a place like Bloomingdales… you’ll find that they try to mirror one of the top end brands.

As a basic rule of thumb, if you can find it on sale… that shoe type/brand is not upper end as the real high end brands don’t have “sale racks”. As an extra point of emphasis, this is why certain high end brands only have certain *types* of shoes that show up on sale on rare occasions.

The Benefits – the Best Part

Quite a lot *should* change over the years (otherwise why are you working so hard!). You should be able to go from “getting looks” because you learned how to have good style/basic dress code abilities (typically just a tailor and clothing from a place like Nordstroms), you then move on to made to measure products with some nicer shoes (anything in the $400-500 range) and then you move to the high-end custom made clothing and brand name shoes/watches (some people even get custom shoes etc.). Now people can complain all they like, but anyone has the ability to at least do step #1 which is learning how to dress with the right colors/fit and prove to themselves it makes a difference. It makes an enormous difference.

#1 Regular People Repellant: That’s right. It actually deflects people who you don’t want to talk to. When people see a well dressed guy with clothes they even know are not cheap.. they will avoid you. This is worth 100x more than the dating category (second) because people literally move out of your way. They will constantly talk smack behind your back and as always.. leave empty handed. A good way to describe the people you’re deflecting? The 3-star review Yelp Crowd. The 3-star review Yelp crowd constantly complains about “prices” for high-end clubs because they shouldn’t actually be there as they haven’t made it *yet*. The 3-star review high end bar/club is going to be your bread and butter since it’s typically the best place (rich people always attract the best looking women). For further explanation of this effect, look no further than the front 10 rows of any major sporting event. 

#2 Dating: This is the second most obvious category. We’ll re-emphasize. The girls who do not care about your clothing/looks are not the girls you want to attract. The ones you want to attract will 100% care that you look good and are “put together” the most common saying. No attractive girl wants to introduce her “man” as a beer swilling, blue jeans wearing slob. Just like her interest in purses and nice shoes, the way you look is a reflection on her as well. The way this scales up is pretty simple, it goes from: 1) more looks and comments such as – i like your overall outfit/look to 2) “where did you get that” to 3) the most blatant = “Nice XXX”. It can get *much* more overt from here but like everything it is an art. Once you’re getting complements consistently, you’ve done it right. Again using the scale, it should go from 1x every 2 weeks to 1x a week to the pinnacle which is “daily” whenever you dress up to your “max potential”. Before moving on here, remember the same old quote, “if she can’t experience it, it doesn’t exist”. You don’t want to be seen with an unattractive poorly dressed woman and we can guarantee you the feeling is more than mutual. You don’t need to look like James Bond 365 days a year… but you better be able to pull it off if needed.  

#3 Self Confidence: Can’t put this into words but we’ll try. If you’re already making good money, you will still benefit by creating your own distinct style and vibe. You’ll go out shopping or look at something and the girl you’re with will say something like “I knew you’d like this it’s your type”. That’s when you’ve essentially hit gold. You’re now at a point where you’re establishing the direction you’re going in life. Besides, you didn’t get rich and succeed to be the same guy did you? Of course not. So once you have hit your stride you’ll slowly upgrade in that “direction”. The baseline clothing slowly turns into throwaway clothing, the second level clothing becomes daily wear clothing and the final level is worn maybe 30-40 days a year. Eventually, you end up with only two tiers, the daily wear clothing and high end which look increasingly similar. Funny how that works!

#4 More Events: A hidden secret of high-end fashion/clothing? You’ll be invited in. If you’re looking sharp all of the time who is the most likely person to recognize high-end fashion… Models and other designers of course. What does this mean. It means those types of people are more likely to talk to you. Take a second and imagine a standard good looking model. Do you see this person talking to someone who looks like James Bond or your average middle aged american. Be honest. We all know the answer is James Bond as this fictional character is easy to compare and contrast with. So. If you’re dressed more similar to a rich James Bond type person, you’re more likely to attract the right crowd. This ends up *saving* you money. Despite what frugal people will tell you, if the ideal version of yourself attracts good looking women, you’ll have a hundred more opportunities by dressing sharp and getting invited to events/house parties. The only other “easy” way into this “level of the video game” is by getting into the illegal drug scene.

#5 More Income Opportunity: Here is the slippery slope. When it comes to rich people there are really two categories, people who are extremely frugal and those that aren’t. By knowing how to dress sharp and do all of the above you’re giving yourself the opportunity to sell to this side of the equation. The frugal side will look down on your style so you should always have that second tier to avoid making them feel insecure/upset. Essentially, by knowing how to look good, you’ll open up a door that’s essentially shut off from the masses and a lot of rich people as well. It’s a good strategy as you never want to close a door when it is full of rich and attractive people. 

Conclusion: This should repel a lot of regular people who confused “stealth wealth” with wearing $10 t-shirts and plastic shoes. It also gives a good hint on how detailed our lifestyle/spending book will be as we didn’t explain when to buy and upgrade (or the types to go for!). For people that are on the fence about all of this we’d say, get to level one first (90% can’t even do that) then take a stab at level 2… then you’ll be 1,000% convinced. You’re not going to go broke wearing nice clothes when you’ve made it. The key here is that you’ve made it. If you’re making $200K pre-tax a year, you’re definitely not going to buy Gucci shoes and $5,000 custom suits. Now if you’re making $50K a month after taxes… you can buy whatever you want and slowly infiltrate the fashion community (it’s worth it!).

To emphasize how easy it is to make a difference you don’t need the ultra high end today. All you need to do is *show* that you’re the type of person who won’t be a cheap guy. If you’re willing to spend a little extra to look good the message is that when you make more, you’re not going be stingy. This is the implied message you send when people see you. And. When we say people, again we’re talking about the ones you want to attract. The guys in the Cole Haans and Aldos will hate on you… This is good (they don’t waste your time).

Filed Under: Personal Finance

Comments

  1. AvatarMoneytrain says

    March 4, 2019 at 10:37 pm

    Fashion is like sex. Deep down everyone wants to have it, but most go about their day forced to repress the urg for it.

    Then those same average people that repress their urg will go tell you that worrying about what you wear in the morning causes decision fatique and they have better things to do…

    Like ok bro but the social ROI IS worth that decision fatique

    As someone who hasn’t “made it” yet, I do know that you can still drastically increase your fashion by perfecting the fundamentals. Lean/atheletic build, clothing that fits/tailored, shirt colors that match your eyes (makes them pop).

    Also found that if you haven’t made it yet, generally better to avoid logos. i.e. rather wear a well-fitting dress shirt with no logo than one with a mid-tier affordable logo. You can still look and feel like a million bucks with $300-400 shoes, fitted $200 dark jeans and fitted shirt.. all no logos..

    But if you want to look and fell like $2mm you better stack that guap to get some real fashion.

    No surprise Drip too Hard was such a popular song this past year. Aha!

    Reply
    • Wall Street PlayboysWall Street Playboys says

      March 4, 2019 at 10:47 pm

      “Also found that if you haven’t made it yet, generally better to avoid logos. i.e. rather wear a well-fitting dress shirt with no logo than one with a mid-tier affordable logo. You can still look and feel like a million bucks with $300-400 shoes, fitted $200 dark jeans and fitted shirt.. all no logos..”

      100% approval of this message. A mid tier brand does things wrong both ways, shows the logo and doesn’t get a return

      Reply
    • Avatar6yhg7 says

      March 5, 2019 at 12:21 am

      Good comment. I felt like a scrub before reading that

      At 23 mines I go white leather sneakers $200+ 200$ jeans and a 20$ Shirt that fits my muscles.

      I guess I need to stick in the Nordstrom territory with 2~3 more pairs of jeans some entry level boots

      Anyone have advice on a good style for Austin, I don’t want a tattoo lol

      Reply
      • Wall Street PlayboysWall Street Playboys says

        March 5, 2019 at 12:45 am

        This account seems to know a lot about basic fashion and lives in Dallas (saw a lot of tweets on our style rant)

        Not sure if relevant but too many coincidences so will leave the link to her/their? Blog/website

        https://positivityrightnow.com/scared-straight-how-i-bullied-my-daughter-into-not-becoming-fat/

        @melissajknows is the Twitter

      • AvatarSaaS Sales Guy says

        March 5, 2019 at 8:11 pm

        I moved from DC to Austin and it’s noticeable how much lower the dress standards are. Chelsea boots & a shirt that actually fits are enough to standout among my age class (24). Upside is warmer weather means means pool parties 7-8 months a year.

      • AvatarSam says

        April 12, 2019 at 9:39 am

        In Austin. Nordstrom’s are plenty man. It’s easy here.

  2. AvatarNB says

    March 4, 2019 at 10:39 pm

    In my experience, you can always judge a person by their shoes and wallet

    Reply
  3. AvatarRE boi says

    March 4, 2019 at 11:29 pm

    a high level move is “dressing down” but still looking sharper than your peers who wore a button down and dress shoes out. Girls notice this. The world has gotten more and more casual, having the confidence to pull off luxy casual wear is a useful skill!

    also sidenote rocking something like suede boots or a leather jacket or something most guys don’t have the guts for will put you ahead as well. Dudes think that a nice watch and those awful button downs with graphics under the shirt cuff are the move…tf even is that..

    Reply
    • Wall Street PlayboysWall Street Playboys says

      March 4, 2019 at 11:56 pm

      Depends on the environment for sure. Suits don’t always work. Sounds like the guys in the spot you go to have no style… wait… that’s 97% of the male population

      Reply
  4. AvatarYo says

    March 4, 2019 at 11:42 pm

    You’re not getting to the root issue. Great body makes clothes look good. I can tell the difference between 500$ dress shirt vs. 100$ dress shirt; however, a great body will even the playing field.

    Reply
    • Wall Street PlayboysWall Street Playboys says

      March 4, 2019 at 11:50 pm

      Nah, still get blown out by guy with the nice stuff body type equal

      Always guys in 20s who argue this moot point, they usually wash out at 32-34

      The point of the post assumes the guy is in shape otherwise… he is so far behind he’s not in our audience base

      Reply
  5. AvatarMshiddensecret says

    March 4, 2019 at 11:44 pm

    Yup fashion is important.

    Was wearing a parka around and everyone treated me like nobody.

    A topcoat with a nice scarf, everyone is suddenly polite

    Reply
    • Avatarmshiddensecret says

      October 25, 2019 at 10:17 pm

      Adding on to this. The BIGGEST game changer for me is ditching the glasses…

      The only reason why I even wore glasses in the past is because I thought I looked better in them (I had pretty stylish ones [circular warby parker style]).

      I’m convinced 99.9% of the time, people look better without glasses. Don’t fool yourself. I’m surprised this isn’t talked about enough.

      Benefits I’m already seeing:
      1. People treat you with a lot more respect (no longer get put in the nerd bucket)
      2. You look more intimidating and less clumsy.
      3. Because of 1 and 2, you can focus less on engaging the conversation. Because people are more interested in talking with you, you can get away not giving a shit, which makes them feel even more attracted to you.
      4. It’s ALOT easier to observe the eye and body language of other people. This opens up a new world of meaning to your interaction. For some reason, wearing glasses made it difficult for me to focus on things “up close” so I missed out a lot of signals.
      5. Persuading people is ALOT easier. Forget about reading sales book. Focus on your appearance first and foremost. First impression is last.

      All of this in just 2 weeks of ditching the glasses. It’s a huge eye opener for me because in the past, I really had to develop my personality to engage with people. With this transformation, I can amplify things further since I know what it is like to be on the other side of the appearance spectrum.

      So if you want to upgrade your life immediately, get contacts/lasik ASAP.

      Reply
  6. AvatarAnon says

    March 5, 2019 at 12:31 am

    Of all the “upgrades” that came with my modest success, the new wardrobe caused the most hate by far. I’ve never experienced anything like it. Not even high fashion, upper mall tier at best.(no branding visible of course.)

    Reply
    • Wall Street PlayboysWall Street Playboys says

      March 5, 2019 at 12:41 am

      Hahaha it gets worse.

      The people who hate you shouldn’t care about anyway.

      Reply
    • Avatarf4432 says

      March 5, 2019 at 4:04 pm

      It’s Brutal. I lie down constantly, tiringly so, and still peoples ego are getting slap boxed every day/week they run into me.

      Once people voices start wavering constantly , or they even “freeze up” around you. Your on the right path

      Reply
  7. AvatarGenCopywriting says

    March 5, 2019 at 6:13 am

    ‘There is just no argument here and studies don’t work since a “study” is based on what people say not what they do. Making decisions based on what people say would result in failed decisions for life’

    This is hands down the best copywriting/marketing advice I’ve seen in a while. Study what people do, not what they say.

    Also explains why modern journalism is crap – based on surveys, studies and not via the good ole’ digging.

    Reply
    • Wall Street PlayboysWall Street Playboys says

      March 5, 2019 at 8:18 am

      Imagine if you took dating advice from women… it would be a rough year.

      Always go based on what people do.

      Reply
  8. Avatarthe red quest says

    March 5, 2019 at 9:46 am

    That’s funny, someone was just asking me about fashion/clothes: https://theredquest.wordpress.com/2019/02/25/fashion-and-clothes-for-players. Wonder if the same guy swung by here.

    Reply
  9. Avatar4betguy says

    March 5, 2019 at 1:02 pm

    European reader here, I traveled the world for years and seen a lots of styles. If you really want to improve when it comes to dressing up and your personal style forget Miami, London, etc. I lived in both and they are overrated when it comes to dressing up and clothes, most importantly they hardly produce top menswear in London or Miami unless in Italy or France.

    Just travel to any Italian city (recommend Florence, Naples, Venice, and also the Italian and French riviera) and observe how the well off people dress. It is the many little details done correctly what gives you that A-look: An example is that Italians will always wear matching colour leather shoes with matching belt, matching handbag if done correctly than also matching wristwatch leather. They look classy regardless of their income buckets. However if you are a tanned and well built Italian with FU money than you will look better than most guys in the latest GQ or Esquire. Sorry Miami.

    Reply
  10. Avatardrnyc says

    March 5, 2019 at 5:33 pm

    Ferragamo

    Reply
    • Avatardrnyc says

      March 5, 2019 at 5:36 pm

      You seem to be generally adverse to Ferragamo loafers. Any specific instance in which they are particularly appropriate? General thoughts on wearing loafers with a suit on a typical work day?

      Apologies if this came through more than once or incomplete… I am traveling and the WiFi isn’t great.

      Reply
      • Wall Street PlayboysWall Street Playboys says

        March 6, 2019 at 6:19 pm

        We explained it above, it’s fine, just don’t wear it with the wrong outfit. Looks terrible

        Just like everything else in life, people hate on fashion since they can’t afford it. Then assume it doesn’t work to protect their egos

  11. AvatarAlly says

    March 5, 2019 at 7:41 pm

    I love fashion. I view it in a much more emotional/personal way though and I’m much more focused on making myself happy when I look in the mirror rather then how other people will react based on what I choose to wear/how I look. If I don’t find myself attractive, it doesn’t matter how many people find me attractive. I will still feel miserable.

    By this post, I’m honestly surprised how men are also into fashion, though. I always assumed fashion and focusing on looks was more of a girl thing. Glad to hear that this is not the case.

    Reply
  12. AvatarD-Train says

    March 5, 2019 at 10:42 pm

    Still far away from where I want to be fashion-wise and life-wise, but I try to look somewhat sharp. Usually wear allen edmonds, and I’ve found propercloth to be pretty good. MTM shirts for 100-150 and you can get fitted in person and have them make adjustments if it doesn’t fit perfectly. One thing I’ve never understood is high end jeans. I usually wear dark jeans from uniqlo (serious) and I don’t see a big difference vs expensive jeans. To me they look kind of weird with weird sticking around the pockets and what not.

    Also, need to seriously work on matching colors. I think you guys posted a good book about men’s color? Color for Men – Carole Jackson..I think this is the one?

    Reply
  13. AvatarTechSalesLatino says

    March 5, 2019 at 11:29 pm

    Spot on as usual.

    I haven’t made it yet, but decided to take the jump and spend on a tailored suit. It’s probably the item that I get the most compliments on.

    Not to mention its comfort and durability.

    The only people who ever teased me or judged me on it were people who wouldn’t be able to afford it.

    Similar to how If a ripped guy goes shirtless he gets called a douche…but in reality deep down they are jealous of his physique.

    Reply
  14. AvatarTechSalesLatino says

    March 5, 2019 at 11:53 pm

    Spot on as usual.

    Haven’t made it yet by standards posted, but working on it.

    I have seen a clear example of this, about 2 years ago I spent on a tailored suit (sub $1000 range.) It is by far what I get the most compliments on, by men, women, superiors, strangers, etc.

    Ironically, the only people who hated on it were people who can’t afford something like this.

    Kind of like in the gym. Muscular guys in tanks will get called “meatheads”, etc… It’s always the jealous out of shape guys doing it.

    Reply
  15. Avatarnorthern plains says

    March 6, 2019 at 7:25 am

    Left my parents home for the first time after college, moved to a new city & have worked for 1 year in tech sales as an SDR, currently making 100k a year total, next step is to move to a closing role. Fore-casted career progress: 140k/year in 2 years, 250k/year in 6 years. Cashflow still not enough but huge amounts of free time (only work 40 hours a week), now I need to build an online business.

    Some knowledge I have gained:

    > people WILL be jealous of your accomplishments. Most of my high school/college social circle is full of average losers who are “too busy to go to the gym” because they’re all so busy with their 40k a year job. I have received nothing but contempt and jealousy from these guys, they will pretend to be happy in your face but they’ll downplay your achievements behind others and try to one-up you in front of girls. I was only “friends” with these losers because we went to the same high school and lived in an isolated suburban street. Without a doubt, if only I cut them off earlier I would be doing a lot better in terms of money, relationships and general happiness.

    > [in the context of a major city with 2k/month rent for an average place] 100k a year is nothing, don’t even try to show off. Don’t try to use money to get girls, you cannot compete with the 100,000s of millionaires in the city.

    This does not mean you have to dress like a slob.

    Get a haircut every 2 weeks, hit the gym, bench 140% of your bodyweight, remain under 14% bodyfat, wear clothes that fit perfectly (brand doesn’t matter, fit/color, Uniqlo is great), $400 leather shoes, keep your testosterone high through healthy lifestyle choices and the girls will flock to you.

    I have found better results from approaching girls during the day than at night, your confidence is a turn on because most losers don’t have the balls to approach sober on the street. Girls on tinder are usually a lot worse than girls in real life – you really do need to speak to someone face-to-face before going on a date with them, although you’ll get lucky occasionally (if you do decide to use tinder just buy gold, you’ll save so much time).

    Also, girls don’t really care about what you do. As long as you look/sound like you’ve got your shit together then its all good, revealing too much about yourself too early is a big turnoff.

    Its truly been a great year for me and I would like to thank WSP for all the advice and entertainment they’ve provided me. I’m still very early on my journey to financial enlightenment but every month has been the best month of my life recently.

    Reply
    • AvatarMaharajj says

      March 8, 2019 at 12:11 am

      Most relatable comment

      Reply
    • AvatarAnonymous says

      March 9, 2019 at 4:22 pm

      awesome

      Reply
  16. AvatarDangerman says

    March 6, 2019 at 9:20 am

    “But what about muh Warren Buffet?”

    Reply
  17. AvatarOP says

    March 6, 2019 at 1:01 pm

    For anything that has resale value there is a market. So for simple items like watch, pen or car, it makes sense to invest some time owning something that is liquid, will limit loss + option for price increase in positive business cycle. This will allow you to have minimal cost of carry and will making trading up easy.

    Example:

    Watches: Rolex sub 14060 2 –> Rolex Daytona —> …..—–> Patek 3940G….

    Insider tips: Heuer Carrera re-edition from late 90ies is a steal

    Cars: 911 (997) –> 993 —-> … —-> Ferrari 458…

    Insider tips: E46 M3 CSL

    You will learn how these markets function (always useful). That is, is my view, a great value add. I often discuss the price trend of cars/watches with other collectors which, if you have the knowledge, is an easy trust builder.
    Furthermore, trading these items in the market means you will learn to sell and buy, which makes rotation easier but also very useful, transferable skill.

    If you really start making money, these skills can easily be applied to the art market which the 50m+ set likes…

    On clothes: fit first, high quality, minimise visible branding.

    If you have a better half, make sure she’s always appropriately dressed. Spend, as she is an extension of your brand. If she is hot, well dressed, charming, and is with you… that is a pretty clear signal.

    Reply
  18. Avatar3462dfw says

    March 6, 2019 at 2:54 pm

    Just browsing Neiman Marcus

    When it comes to High end jeans of like $200+ for early twenties male

    Do You shift more towards
    1) Chelsea/Chukkas with classier Jeans.

    2) Or that edgier style skater looking jeans with high end sneakers

    What do you guys do?

    Reply
    • AvatarAnonymous says

      March 8, 2019 at 4:31 pm

      edgy jeans are great if you’re in s creative industry like tech or marketing, if you’re a banker pick more conservative since that is congruent to the image.

      Reply
  19. AvatarJohn says

    March 6, 2019 at 7:10 pm

    Thanks for the post. Can you elaborate on fashion circles (how to get in, why it’s worth it)?

    Reply
  20. Avatarnyc chillin says

    March 7, 2019 at 11:30 pm

    Honestly I’m not about the type of girls that care about brands and incremental status branch swinging, etc. I like wearing low-key outfits that are essentially enough to convey that I am self-aware. I want to attract the girls who can look good and play the part but are also self-aware and not super Machiavellian. Money isn’t forever and shtuff happens in life where how much money you have doesn’t matter, and I don’t want girls (besides one night stands) to like me because they know I have money to buy things. It’s a trap.

    I will say I feel great when I have a nice-fitting and high quality piece of clothing on. But you really don’t need to spend much for that. 100 dress shirt, 100 jeans, 250-400 shoes?

    For work in nyc I wear some banana republic dark blue khakis that fit nice, a Charles Tyrwhitt shirt that fits great (4 for $80), and my coat is this Joseph A Bank quilted mid-cut winter coat that is really nice ($30 on big sale). I’ve gotten like 3 compliments on it in the past 2 weeks.

    I do need to upgrade my leather wingcuts to Allen Edmonds.

    But I walk down Lex every morning/evening and I get looks and direct eye contact from plenty of girls.

    If fashion is your “thing” that you like, then go for it. People will just be inspired that you are inspired about something. But if it’s not your thing, just wear something that fits you well, has high quality material, and conveys your vibe. Nothing more needed.

    What do you other guys wear when going out dancing and having a few drinks? I wouldn’t want to scuff up nice shoes.

    Reply
    • Wall Street PlayboysWall Street Playboys says

      March 8, 2019 at 12:38 am

      It’s only $500-800 who cares if they get scuffed just shine them and replace every couple years

      Reply
  21. AvatarFullTimeFinance says

    March 8, 2019 at 7:55 am

    Honestly you’d struggle to argue I’m frugal in the traditional sense, but I’m not with you on the nice clothes here. I just don’t care, never have. It’s not a frugal thing, it’s more a priority thing. Wearing high end clothes is not for everyone.

    The more wealth I become the more likely I am to walk around looking like a slub cause I don’t need the roi the clothes provide.

    Then again my affliction is sports cars. We all have our things, you do you.

    Reply
  22. AvatarKayee Tong says

    March 8, 2019 at 12:19 pm

    Thoughts about waiting for economic crash before going on a massive shopping spree when people dump their Loro Pianas, Rolex, Bugatti etc?

    Reply
    • Wall Street PlayboysWall Street Playboys says

      March 8, 2019 at 12:24 pm

      This isn’t a Q&A but anyone who is rich knows that the *real* luxury market actually sustains totally fine in a recession.

      Just the mid tier half brands that go on discount as those were affordable to the middle class on leverage

      Reply
  23. AvatarAnonymous says

    March 8, 2019 at 4:18 pm

    Big advice for anyone 1-2 years out of college.

    There is a very big message in this post that you cannot frugality your way out. Ask someone who’s making 400k+ (single) if they avoid spending an extra $500/mo (6k a year) on a larger apt closer to their job/biz just to ‘save’. They are more than aware that 6k is nothing if they can get even extra 10% a year in income. If you aren’t here yet (some might be) be warned that everyone in a ‘high paying’ Industry like tech or banking will keep selling you on saving every last penny. If you find yourself getting into this mindset, immediately reread this blog to get out of it.

    Reply
  24. Avataremonies says

    March 8, 2019 at 10:02 pm

    Great write up as per usual. My typical style is neutral tones and dressing smart without looking loud, too edgy or fashion forward. Timeless style will never be out of fashion. Here’s a quick and dirty guide to a few designer brands for guys in their 20’s and early 30’s:

    Theory – Understated luxury with muted colors. Great basics with perfect fits. My go-to brand for slim fit styles and dressing smart without looking like you’re trying too hard.

    Common Projects – Clean, minimalist sneakers. Everyone always asks why would anyone pay $400 for a simple looking shoe, well, because it goes with any outfit and super comfortable.

    Givenchy – If you like black, this is your line. Nice fabrics, fits and suits those with dark tastes.

    Berluti – Upscale and elevated for classy evenings. Amazing leather construction like their dress shoes, a step above Allen Edmonds.

    Tom Ford – Reminds me of J.Crew but with better fabrics.

    John Elliott – Best t-shirts hands down.

    Thom Browne – Luxury lounging. Good for hoodies and sweats.

    Officine Generale – Neutral hues, great fits and affordable prices for what you get.

    Moncler – Anyone in a snow state needs a Moncler jacket.

    Saint Laurent – Rockstar vibes. Leather jackets, button down shirts and slim fit jeans are a must-have for those days when you want to not look too basic.

    Reply
  25. AvatarHenry F says

    March 9, 2019 at 3:21 pm

    Another truth bomb by u guys. Seriously best blog best TWTR. The first thing I look forward to reading each day. Those who hate are just haters or not on the level yet.

    Bottom line clothes matter, image matters. Don’t give me this I’m rich I can wear what I want BS. Want to be a Boss? Dress like one, you will feel like one, and you will think like one, and you will become one. Anything that gives you an edge.

    Cole Haan is not luxury its a basic shoe. I have a pair and only wear in the rain.
    Ferragamo – Solid shoe, I wear this as my every day can’t go wrong for work and clients. It’s not the same level as high fashion brands. I’ve never had compliments on them like my others.

    Important items. Must have luxury dress shoes, must have high-end coats, jackets, blazers. It matters the material and cut is different. People notice and the ones who don’t you don’t care for anyways.

    Gotta have a nice watch- You don’t buy a Rolex to tell the time like the small minded think. I met a new client he saw my watch and we talked about watches for next 30mins. Boom done commission earned.

    Dress shirts- I like custom dress shirts and I can choose the fabric. Actually cheaper than buying $150-220 shirts from dept store. Better material and cut perfectly to you.

    Nothing sadder than seeing a rich guy buy nice brands and have everything fit incorrectly. 90% of men buy the wrong size. Just size down 1 you will look 10x better.

    Suits – Right now I get them tailored still not on the level of getting a fully custom suit. That is my next purchase.

    Look forward to reading more of your content. Keep killing it with priceless stuff.

    Reply
    • Wall Street PlayboysWall Street Playboys says

      March 9, 2019 at 4:06 pm

      Yep. They miss the point. You don’t “need” to go luxury. You simply do when you’re rich enough that it won’t impact you.

      We still recommend basic tailoring, $250 shoes such as Allen Edmonds or To Boot New York until you get rich.

      The return is *definitely* lower when you go from made to measure to custom/high end brand. But there is 100% a return.

      So that’s the point, when you think $500-800 on shoes is “tiny” compared to your budget then simply do it.

      We’re 1000% against buying all luxury items if you cannot afford them. And. Please don’t say you wouldn’t at least try if you we’re worth $10M for example. That full wardrobe upgrade would be less than 1% of your net worth.

      Btw the point about not going custom yet was also key, it means you’re upgrading at the rate your life is changing which is perfect!

      Reply
  26. AvatarJay says

    March 9, 2019 at 9:18 pm

    I bought a $60k AP, always felt embarrassed wearing it outside and thought people are judging me trying to show off. I guess after reading this I can wear it with more pride. In Sydney I have never seen a person with a nice watch, AP, Patek VC etc, only Rolex’s here.

    I need to get out of this country, do you give private one on one coaching? I have got enough money now, but all my friends are low lifes, uneducated and broke. Unsure what I should do.

    Reply
    • Wall Street PlayboysWall Street Playboys says

      March 9, 2019 at 11:27 pm

      Hahaha nice troll if true and rich then just go out consistently to *nice* spots 4-6x a week until you meet some better people.

      Reply
      • AvatarKurt Burum says

        March 10, 2019 at 10:12 pm

        Its not a troll, I am after consulting/email me if possible, Sydney is very hard to make new friends, or Australia in general, everyone are the same group of friends since high school mostly. I want to ask some other questions as well.

    • AvatarBrent says

      April 7, 2019 at 10:41 am

      Don’t forget about going to high end gyms. Also BNI (business networkong international) groups.

      Reply
  27. AvatarMKB says

    March 10, 2019 at 4:14 am

    Certainly I’ve noticed the level of respect correlates highly with dressing sharp. That said, sometimes a healthy dose of not GAS is called for, and it’s tough to do that in a bespoke suit no matter what your personality. I used to be self-conscious if I was slightly underdressed at say a networking event, but now find dressing down a bit to be a confidence-booster and projecting an image of non-desperation (esp. important in the presence of women).

    Reply
  28. AvatarJon says

    March 11, 2019 at 6:13 pm

    This post is excellent.

    More thoughts on why dressing well is worth the effort:

    If you don’t look after your self how can you look after a business, a sale or a relationship. All relationships are built on trust. Clothing is a great social filter.

    Birds of a feather… People like what they like. They like what is similar to themselves. Dress like the people you want to be with/know.

    Reply
  29. AvatarJeffrey Law says

    April 7, 2019 at 9:57 am

    Status items work. I wear a Rolex regularly and, girls, even when they don’t comment on it, do notice it.

    If status items didn’t work men wouldn’t buy them.

    Interested to hear your thoughts on other status items (eg branded wallets, luxury cars, etc).

    Reply
  30. AvatarJohn Andre says

    April 7, 2019 at 10:15 am

    I don’t get the early retirement/frugality crowd…I stay home for two days and I’m bored out of my mind.

    I do disagree on one point, not all luxury items are worth it, especially cars.

    Living in NYC, don’t even need a car. Was a valet for years, a mid-range luxury car is fine, barely noticed the difference…

    Then again, depending on your job, cant pull up to clients in a Camry…

    Good post again!

    Reply

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