Disclaimer: If you are the frugal type, please skip this post. You will not derive any value from it.
Good fashion sense and frugality are antithetical to one another: Frugal individuals subscribe to scarcity and are too focused on cost-cutting irrespective of how well they are doing, while good dress style involves a progressive escalation in spending to keep up with your progression through life. Irrespective of how much you try to limit and reduce your expenditure, you will still be spending money that gets deducted from your bank balance. Not to mention that you will be far better off taking the approach of increasing your spending to position yourself to exponentially increase your income/cash flow.
In the first section of this post, we will address the overall principles to follow to derive the greatest ROI from how you spend and dress. In the second section, we will go over how to spend on fashion based on what stage you are at in life.
Section I: Principles to Follow
Common Arguments Against Spending on Good Fashion
1) “Not Worth the Price”: This is the standard, entry-level excuse. People who are broke and don’t have much going for them (usually married, middle-class men) are infamous for making the assertion that luxury items are never worth the price. The reason? Simple. They are in denial because they can’t afford to buy it for themselves, and if they were to publicly acknowledge the alternative then they would be obligated to upgrade their own wardrobes. But this won’t make much of a difference as most of them are out of shape to begin with. Anyone who has made it knows that the quality of reputation of the goods that you own can make a huge difference. Once you have achieved a certain net worth and reached a certain age, you will actually lose $$$ and social status by dressing several tiers below your actual financial capabilities. Therefore, the only thing that is not worth the price is being too cheap as you will end up overpaying substantially in terms of what you ultimately lose out on.
2) “Nobody Can Tell The Difference Anyways”: This excuse is even more common but absolutely absurd. There are plenty of studies out there that proclaim that the majority of people don’t know the difference between the definition of a robbery and a burglary. There are also studies that show that women don’t care about how muscular a guy is. From real-life experience, we observe that both are largely wrong. Unless you spent your entire life living in an igloo, you know that when it comes to attracting women looking muscular is better than not looking muscular 100% of the time. Of course, there is more to it as there is a difference between looking muscular and looking physically attractive (being extremely muscular can do you a disservice and does not equate to being physically fit). Nonetheless, it doesn’t take much real-life experience to come to the conclusion that studies are more often than not unreliable since they are based on what people say in public and not what they do in private. Good examples would be social media behavior and racism. Ask any guy if he stalks girls’ profiles on Instagram and he will deny it, but the reality is that 99% frequently engage in this. Likewise, ask anyone if he/she is a racist and even the most outright vocal racists will deny being one. These are two extremely obvious examples that just prove the absurdity of common data extraction methods used in research such as surveys.
3) “I Don’t Like To Wear Extravagant Clothing”: When you go home today, go to your closet and rummage through your entire wardrobe. Then change into the nicest clothing that you have which you wear only for the most exclusive events. Then look at yourself in the mirror. Notice any difference? Yes, you feel more confident and your sense of self-importance has gone up. Unless you are terrified of positive momentum and major positive developments in your life or you are intentionally suppressing your feelings, then you know you suddenly feel a million dollars richer. Yes, that’s the effect of dressing nice and with care to your image: it changes the way you feel for the better. So we would say it is very worthwhile to dress nice and that this excuse doesn’t hold any weight.
4) “Most People Who Dress Nice Are Superficial and Are Either Spending the Majority of Their Income on Expensive Clothes or Purchasing on Credit”: Switch the word “most” with “some” and then there is truth to this statement. Sure you do see a lot of unsustainable debt-funded status chasing among millennials and the Gen Z crowd, but the lion’s share of revenue within the luxury clothing market is dominated by big buyers who are wealthy. These big buyers often don’t just purchase a single unit of anything. They usually have a set of products that they rotate at minimum. If you go to the same high-end venue time and again, rather than speculating that the other clientele are simply there to flex for a one-time occasion, keep track of whether or not you see the same faces coming back. If you come across recognizable people over and over again who are always dressed the part, you can be sure they are rich and simply groomed to reflect their actual financial status.
Common Spending Mistakes
1) Conflicting Items: The tier of the items you are wearing/visibly displaying must match. This means you shouldn’t walk around dressed to the nines in a $5K suit only to pull out a $15 wallet to pay for coffee in front of your hedge fund client. It’s a bad look and while most average people won’t notice something as insignificant as this you can be sure that someone who is truly worth impressing will. There are certain exceptions to this though. For example, if you’re wearing an $8K Omega watch but rocking a pair of $5 socks no one will notice. On the contrary, having one or two inexpensive bespoke items with no branding visible can even be advantageous as they often come with a good story which is exactly why you are wearing them. Pay attention to clothing/accessory items that different people complement/ask you about more than once- they attract positive attention that in turn makes you more memorable.
2) Inability to Read the Surrounding Environment: The great thing about being dressed well is that you do not need to wear top-tier luxury brands at all times and you also don’t need to jump immediately from the low-end to the high-end. It takes a natural progression of several years of observation and experimentation to build your individual style to a level that works best for you and generates the most positive reactions according to your own height, body type, vibe, personality, skin complexion, preferred venues, etc. To give a basic example, if you are going out in Nice or Dubai you should definitely not be dressed the same as a guy based in NYC or London. Every city comes with a different vibe and accordingly requires moderate shifts in dress apparel should you be looking to place yourself in the most advantageous position. Ignoring this reality is a common mistake. People think they can just wear the same rotation of clothing all over the world and have it work seamlessly. That’s not how good style/fashion works.
A frequent mistake we have personally observed time and again is when people receive their first major payday, usually their first big bonus check or some form of event-driven income that increases their net worth overnight by several multiples. They will go out and buy a couple of items like Santoni loafers and a Rolex watch, then wear these together with their existing outfit. This sends out the wrong message that you are trying to generate attention by showing that you have one or two items that are high-end. Even worse is when the shoes don’t match the clothing because this is one of the first things people notice. Whenever the color and style doesn’t match, nobody of any importance will care about the brand or tier.
3) Overcompensating: One really common mistake is to try and simultaneously do everything in the same range all at once. This is overkill. If you are headed to a very ordinary venue like a dive bar (yes it’s fine to head here particularly if you are early in your career) where there won’t be a single suit in sight, leave the $10K cashmere tux at home. Aim for something more appropriate like a pair of high-end jeans/khakis, shiny high-top sneakers, a leisure blazer and even a regular form-fitting t-shirt that emphasizes the positive aspects of your upper body build. The objective here is to stand out in a good way that still aligns more or less with your surroundings, not to be so over the top that it becomes obvious to everyone and their mother that you have intentionally come into a cheaper venue to stand out as a big fish in a small pond.
4) Overspending: Some overspending upfront is inevitable as it is part and parcel of figuring out your style and making the right adjustments to your wardrobe. This becomes easier and less of a problem once you figure out the exact type of audience you are targeting. Unless you are completely sure about the type of venues you enjoy the most, the cities you will frequent in the future, and the crowd you want to surround yourself with, then trying to tailor a bespoke style to your audience will never work and you will not get the results you desire. As an example, you don’t want to buy Ferragamo loafers if you prefer to operate in tailored suits and spend your time frequenting champagne bars. Rather, you would want to invest in a collection of design oxfords and double monks.
Additionally, if you have some general hunches but have not discovered your long-term style and lifestyle preferences yet, pick out a starter brand. If you go through the catalogs of all the upper middle-range brands at a place like Bloomingdales, you will see that their designs all resemble one or more of the high-end brands.
Keep in mind that anything you find on sale is usually not high-end as high-end brands do not have “sales” racks. Part of the allure of high-end brands is the image of exclusivity: the overwhelming majority of their repeat customers will stop purchasing their products the moment this image is in doubt due to “promotions/discounts”.
The Benefits of Dressing Well
When it comes to your fashion, a lot should change over the course of 2-3 years. Assuming you are doing it right, you should go from generating occasional looks from passersby because you learned and applied the basic fundamentals of good dress code, then transitioned to made-to-measure goods with upper-middle tier footwear ($400-600 range) and ultimately to the more exclusive higher-end custom clothing and established brands for shoes and watches. If you are still at the very beginning stages of this journey, here’s how it will improve your life:
- Increased Confidence: Most people have a tendency to dress the way they feel, and if you are feeling down or unmotivated then you will be more inclined to wear uncomplimentary clothing. With this in mind, you can make modest alterations to your mood by simply selecting a better and classier outfit then you had originally intended. Instead of dressing in sweatpants and an oversized Yankees hoodie, pick out an outfit with elegant prints, saturated colors, and a flattering fit. It might seem like a small difference but it will modestly lift your mood and confidence and send you out the front door with a smile. Do this every single time you feel down over the course of six months, a year, two years and beyond. These small incremental changes will merge and compound until your confidence level makes a permanent jump, which will in turn translate to improved performance capabilities and experiences.
- Dating Scene: The girls who do not care about your physical appearance or how you dress are not the type that you should be interested in attracting. The ones you should want to attract will most certainly care about you looking good and dressing with thought and care. No high-quality girl is interested in introducing her man to those close to her if he is dressed in an oversized hoodie with Target jeans and worn-out sneakers. Similar to her being dressed elegantly, how you dress is a reflection upon her as well. This should scale up from: 1) more pleasing looks and remarks i.e. “I love the colors of your outfit” to 2) “Wow, where did you find that?” to 3) “you look so good today”. We don’t want to go any further but from personal experience it can get substantially more expressive from here (yes, you know what we are implying). Going back to compliments, once you are receiving them on a consistent basis you can be sure that your dress style is right at least as it pertains to dating. As you make minor tweaks and the occasional major upgrade, the compliments should go from 1x/week to 2x/week to daily. You don’t need to be dressed like Patrick Bateman or Jay Gatsby 365 days a year, but be prepared to make the effort should it be necessary.
- Ordinary People Repellant: When people see an attractive, well-dressed guy donning clothes they know are pricey, they will literally stand up and get out of your way. Why? Because you being in their vicinity will draw attention to how average and shabby they look in comparison. There is a huge benefit to this because once all the normal and low-value people have moved out of your way, the only ones left will be the high-quality ones who feel comfortable being around you and are most likely interested in making your acquaintance too. This is the literal definition of killing two birds with one stone. Returning to the dating scene, the effects become greatly enhanced. The attractive girls will be drawn to you, while the loser guys will talk sh*t about you and leave feeling depressed and empty-handed. These are the same guys you find on restaurant/club review boards complaining about the “exorbitant prices”. The reason? They don’t actually belong in such venues because they are not at that level. If you ever come across any venue where the vast majority of complaints tend to revolve around how expensive it is, there’s a decent chance that this is a great spot for those who have already made it.
- Getting Invited to More Events: This should come as no surprise. People who dress well are more likely to get invited to various events, particularly the more exclusive type. If you are always dressed sharp at the right moments, you will attract the right kind of crowd and build a powerful network you can leverage off of going forward. As you find yourself attending more and more exclusive guest list events, these types of networking/social events will become your baseline and your potential opportunities will grow 100-fold.
- Increased Income Opportunities: There is something to be mindful of here. When dealing with the wealthy crowd, you will encounter two types of rich: Those who are very stingy and will fight you over everything, and those who can be easily sold as soon as they see value. By dressing sharp with high end clothing that emphasizes your build and colors that make your eyes pop, you are positioning yourself perfectly to sell to the left-hand side of the equation. The stingy side, however, is prone to feeling insecure if faced up to this version of you in a physical setting, so you should have a rotation of back-up lower-tier outfits to de-risk yourself from the possibility of triggering them.
Section II: The Specifics of Clothing, Shoes and Accessories
Level I – At the Very Bottom with No Sustainable Income: At this stage you are at the lowest of the lows so even the most basic expenses on fashion are superfluous and need to be avoided at all costs. The only genuine decent expense items you really need are a decent suit, dress shirt and pair of dress shoes for job interviews as you don’t want to lose out on a great career opportunity due to having an unkempt appearance. The brand of the shoes does not matter as long as it looks clean and polished.
At this stage, you don’t need any accessories. If you receive an accessory (watch, pocket square, sunglasses) as a gift from a friend or relative, you should sell it immediately. These items will not generate enough additional value to justify retaining them, and you will be better off with extra cash at this stage which you can put into your emergency fund or spend when a more significant opportunity arises.
Level 2 – “Out of the Abyss” Scenario: At this stage you have surpassed a decent income level ($100K+), and now is the time to begin paying more attention to dress as a means of investing in your future. It is important to look the part when it comes to building your career or progressing with a business, and upgrading your appearance when you are in the beginner stages will without question give you a high ROI.
For starters, the direction here is to go for the classic style in men’s fashion. At the most basic level, this refers to the manner of dress inspired by the clothing and prevailing tastes popular among men from the Golden Age of Menswear (approximately 1920s through to the mid-1960s). Classic style has stood the test of time and never goes out of fashion, meaning it can be worn and appreciated just as fluidly today as at its peak of popularity. This comes down to the ability of the classic style to repel the influence of transitory trends and crazes and instead zero in on simple, graceful apparel that emphasizes the male form in a visually charming manner. This means you can wear this look both in the workplace as well as for going out to social events from time to time.
- Building Block Items: Stick with brands where a typical long-sleeve t-shirt retails at around $30 and slacks at $40-$50, so basically the range of classic outfits, timeless fashion and decent quality garments that do not cost a fortune. You can get the basic apparel that fit the above from brands like J. Crew, Bonobos, Nordstrom, Banana Republic, etc. There is no point jumping further above this (i.e. Brooks Brothers) as there isn’t going to be much difference in the quality of durability of clothing and you are just aiming to do the bare minimum to look more presentable at work since you do not have real money yet.
- Basic Rotation of Suits: Up until now you have been managing off of a single suit and it has not been easy. The good news is you can now afford to expand your wardrobe to a total of four suits (three new ones). It’s up to you whether you want to go with bespoke tailoring or made-to-measure. With the budget criterion in mind, we would recommend that you stick with made-to-measure at this stage. Made-to-measure outfits are essentially a combination of bespoke and off-the-rack, while bespoke is completely unique and fabricated to make the wearer stand out more, and are therefore substantially more expensive than made-to-measure. It is very much possible, however, to get your hands on bespoke garments if you are able to get creative in your search. As with the first point, there is no justification at this point to exhaust your funds on acquiring either super high-end suits or more than three new ones.
- Basic Accessories: The only accessories you need at this stage are three to four combos of ties and pocket squares. Feel free to add in a couple pairs of cufflinks too if you have shirts that require them. DONE. You don’t need anything else besides this, most certainly not watches. Buying an Omega or Rolex at this stage will set you back significantly and unnecessarily increase the expectations of those you engage with. Stay humble and don’t let vanity take over when you are still in an arguably shitty position in life.
Level 3 – Entering the Early Stages of Sweetness: Things are starting to look up for you now as you begin to clear more than $250-300K in annual income. This is also when expectations will grow for you to make a bigger impression with your attire. At this stage, you should already be decently well-traveled with a load of international business trips under your belt. This should be invaluable in providing you with further insight when it comes to dressing up and deciding your personal style. It’s not necessary to dress in name brands to reach this standard (although we will provide a number that work well). With that said, it becomes very important to ensure that all the little details are implemented correctly in order to give off that A+ look. If you are traveling to any Italian city for a personal or business trip, take some time to observe how the Italian guys dress. You will notice that virtually all of them wear matching color leather shoes with a matching belt and matching wrist watch leather and look very classy even though their income levels are way below your own. This is exactly the type of gold standard you should aim for and incorporate into your own style. You will know if you are implementing it correctly or not when you start receiving compliments from people on a consistent basis.
- Ramp Up The Whole Image: This means everything, from your home to your wardrobe to your choice of wheels. If you own a $10K custom suit along with a Patek Philippe watch but are still living with two roommates living off of pizza deliveries from Dominos and driving a beat-up Toyota pickup truck, it will damage your image as people will see you as trying to project a certain image that you cannot afford to fully live up to. Therefore, make sure that once the transition is in gear you take care of all the necessary moving parts.
- Upgrading the Brand/Transitioning to Full Bespoke: There is no single correct approach to this. Depending on the style that works for you, you can either upgrade to the next tier in brands or move in the direction of more bespoke products. Brand upgrades are very straightforward. Instead of J. Crew and Banana Republic you will now purchase brands like Giorgio Armani, Charles Tyrwhitt, Mack Weldon, etc. Don’t go into Gucci or Moncler just yet– save them for when you have truly made it and have the option to no longer work because you are set for life.
- Okay to Venture Into Watches: It isn’t necessary to move into watches yet, but if this is something you are passionate about then go for it. A nice watch goes well with a classic suit in nightlife venues and will help you network with other wealthy individuals as well as socialize with women. Don’t overdo it though and just stick with a standard Rolex or Omega. The Patek Philippes and Audemars Piguets can wait until you have reached the next level as only the truly wealthy will recognize and appreciate them.
- Wardrobe Upkeep: At this stage, you should only be purchasing items of clothing that you are willing to take good care of (i.e. the quality is good enough to justify doing so). Naturally, this does not include clothes for exercising and outdoor activities.
Level 4 – You’ve Made It, Time to Spend Real Money: Before we delve in, we feel it’s important to note here that none of the points below are mandatory. When you are actually rich you don’t need to buy anything extravagant if you don’t want to. Yes, you don’t need those $20K suits or those $1.5K Tom Ford loafers. Our sole intention is to provide a framework here that will lead to improved results compared to Level 3. For instance, buying an Omega and switching to a Rolex or higher-tier Omega won’t make a difference. Likewise, the effect of going from $600 shoes to $900 ones will be close to none.
- High-End Name Brands: Assuming you choose to go in the direction of major wardrobe upgrades, the most recognizable goods are typically Gucci, Versace, Moncler, and Louis Vuitton. If you want to venture out into equivalent brands that are more niche, it may be worthwhile finding a paid consultant to advise you on how to pick out clothes and dress accordingly.
- Watches: If you want to make a real difference here, you will need to jump from a $5-10K watch to something $50K+ ($100K is the baseline to be recognized by UHNW). Think Patek Philippe/Richard Millie/Jaeger LeCoultre.
- Accessories: At this level, so many people upgrade all the major items in their wardrobe but overlook the need to do the same for the smaller items, either because they genuinely forgot or because they don’t see the need or importance of doing so. Big mistake. As we have already reiterated time and again, congruency is critical in fashion, especially the higher up you go. At the lower levels you will stand out just as much (if not more) than you would at the higher end, but other people are far more likely to forgive your lack of congruency because they recognize that you are bound by money constraints. This justification flies out the window the moment you don so much as one moderately expensive item. The cost of accessories must keep up with the level of your overall outfit, making up around 10-15% of its overall retail value but not exceeding 20%. This includes anything that is publicly visible such as ties, belts, and cufflinks, but does not include your watch.
- Abundance of Cash on Hand: Not exactly related to your dress but certainly connected to your overall image is the need to always have a substantial amount of cash on hand. Waiting for stuff while being all dressed up looks strange and cash can greatly reduce waiting times (i.e. skipping lines, paying for bills more quickly).
Conclusion
Like with some of our other posts, we are sure that this post has probably offended some people. For those of you that feel this way, our response to you is to try to get to Level 2 first (yes, we know the vast majority of you are currently still Level 1). Your life will improve noticeably once you level up and when you reread this post again at that stage it won’t seem so offensive anymore.
As for the rest of you, of all the upgrades you make in your life, two in particular will generate the most hate from average people who know you: getting into better physical shape and transforming your wardrobe. The two go hand in hand as you can’t pull off one at maximum effectiveness without simultaneously doing well in the other. If you are extremely out of shape but dressed to the nines in luxury wear then you can 100% expect to attract the wrong crowd who are looking for nothing more than to leech off of you. Ignore the hate from all the average people. As you level up, there will be fewer and fewer of them in your life as they get replaced by a higher-quality crowd that will add real value.