Freakonomics Radio recently aired an episode in which they discussed the normative social practice of wearing belts as opposed to suspenders, which the producers clearly found more comfortable, effective and overall a better solution to the persistent problem gravity presents to keeping ourselves decent. In it, they present an anecdote about a famous Indonesian artist who was invited to come to England. He refused, stating that the severe discomfort inflicted by trousers and shoes, as opposed to sarong and flipflops, was too much to bear.

In it, they consult fashion historian (yes, those do exist) Chloe Chapin to get to the bottom of this critical fashion mystery. The short answer: the Duke of Windsor, aka King Edward VII. During his time (mid-20th century), princes were notorious for sporting outfits thought to be too casual by their elders. One of these statements was the belt, which was a primarily American trend, and was seen as a very casual accessory. Starting with the Duke’s closest friends and rippling outward to general society, the belt became a symbol. As Chapin explains, “his friends that were sitting next to him and, you know, those people would have dinner with someone else, and they would be like, ‘Oh after dinner I’m unbuttoning my jacket, just like the prince does. You know how I hang out with the prince all the time? Because I’m so important?’”

mensfashion-6This is just one of a multitude of interesting ideas presented in this episode, so do yourself a favor and check out the rest here. However, this particular idea made me realize that “functional clothing” doesn’t simply mean something comfortable and effective, like suspenders. Apparel also serves a social function that can be just as important as being cozy. Who knows what opportunities and experiences that artist could have had in England? All those potential fruit were wasted by his refusal to accept the full functionality of clothing—both the physical and social aspects.

I believe that embracing the full spectrum of clothing’s functionality is the cornerstone of modern men’s fashion. The word “fashion” has a connotation of femininity that scares a large portion of the heterosexual male community away from even Googling the term. But in a reality where humans’ evolutionary background forces us to make subconscious snap judgements based on first appearances, and where globalization is making cross-cultural travel more and more commonplace, what you wear and the way you wear it is probably more crucial to achieving your goals than you think.

Once you accept this principle, there should be no qualms about entering the world of men’s fashion—it is not a senseless or girly obsession with an endless barrage of ridiculous celebrity-generated trends or a based attempt at superiority by arrogantly displaying material wealth. It is simply having an awareness of the impressions your apparel has on those around you, and, like any sensible human, leveraging those impressions to your advantage by collecting the right articles of clothing. The optimization of this advantage is what I like to call having a dope as heck wardrobe.

In an attempt to convert the multitude of sensible men who have not yet realized the benefits that a respect for men’s fashion can have, I have provided below a few items and behaviors that define my personal style, and why they are at the locus of physical and social functionality. But that’s the most important part—that it reflects your style. What’s functional for me may not be functional for you. So take the following not as strict guidelines or rules, but as general model of how to think about clothing. Stepping a little outside your comfort zone can never hurt, but keep in mind that the right collection of clothes is going to feel right. Ultimately if you feel very uncomfortable in anything, it’s going to weigh on your psyche and manifest itself in your actions, and unconfident actions are the opposite of what men’s fashion can accomplish.


1: Tailor It

The way an article of clothing fits is far more important than its brand, material or design. It sends a subtle signal that you know what you’re doing. There have been studies that demonstrate the positive effects of wearing tailored suits. After looking at men in tailored and untailored suits, participants predominantly selected those in tailored suits as more successful. While this isn’t a cheap practice, there are ways to find great clothes for dirt cheap.

2: Thrift Shops are Your Friend

I have an unusually lanky build, which makes finding shirts that are both long and skinny enough of a challenge. However, thrift stores are loaded with XL and XXL shirts that don’t fit the average shopper. These shirts, which are perfect in length, often run me about 5 bucks. I simply take these to the tailor to have them taken in, which will only cost $25. So now I have a closet full of perfectly fitted shirts for a fraction of the cost of shopping at first-hand stores. Men’s fashion is relatively static—a solid white or blue oxford is always going to be in style. While you’ll want to be wary of dingy or tattered items, thrift stores are full of hardly-worn gems ready to find a new home.

3: Minimize Logos

While sporting pieces that proudly display a little sheep or alligator logo can heighten the public’s perception of your social status, I choose to steer away from them to avoid the hint of pretention they add to an outfit. While designers often do produce genuinely sharp collections, they’re pretty easy to imitate at a lower price point. Reddit’s “Two Budgets One Price” forum offers great alternatives to high end lines.

4: What the heck is going on with watches?

They’re getting out of control. I see more and more men walking around with quarter-pound behemoths chained to their wrists. I like to keep the diameter of the watch face smaller than the width of my wrist, and the height no thicker than four stacked quarters. I shy way from overly intricate dials as well. A watch tells time, which isn’t a terribly complicated task. I look for a design that reflects the simple yet dignified responsibility of keeping time.

5Dress For the Occasion

Like wearing clothes that fit your body, wearing clothes that fit your activity quietly says, “Hello, I am competent and forward-thinking enough to successfully navigate logistical challenges and respect societal norms.” For example, if you’re going to a bonfire or outdoor activity, leave the fresh kicks at home—it is very tedious to try to avoid dirtying them and you’ll spend more time worrying about the conditions of your sneakers than the people around you, which is so lame.

6: Crotch Blowouts and the Rise (?) of Men’s Jeggings

I have spent over $100 in the past year repairing denim. Apparently, there is a point on the upper thigh that simply cannot withstand the friction caused by the pant legs rubbing together as I walk. After about 3 months of every other day use, I have to take my jeans to get patched up so that I don’t have to spend even more money on a new pair, or constantly expose my undergarments to those sitting across from me. Alas, the Japanese company UNIQLO has started selling pants made of a stretchy cotton-polyester-spandex blend that is immune to this fatal weakness of denim. While they are, in essence, jeggings, a fad that was swiftly mocked out of style in the world of women’s fashion, they are too good to resist. No one can tell them from regular dark-wash denim, they’re virtually indestructible, comfortable as hell, and only cost 30 bucks a pop.

7: Iconic Pieces

James Dean has the stark white tee. Bill Nye has the bowtie. Johnny Depp has the fedora-scarf-abundance of jewelry combo. Finding a unique accessory or article of clothing that speaks to you and wearing it regularly is a great way to convey an air of originality. I found a sweet pair of gold-trimmed RayBan Clubmasters that a lot of people now use to distinguish me from the next bearded twenty-something-year-old hipster.

8: Flannel: Me as a Human Incarnated in an Article of Clothing

While I do avoid them in the hotter months, flannel shirts are the epitome of everything I look for in clothing. It’s comfortable, keeps me warm, and is durable, fulfilling three very important physical aspects of clothes, but also has excellent connotations; when people think of flannel they think things like “cozy,” “colorful,” “pancakes,” and “lumberjack,” which are all words I would be very happy for people to associate me with as well. This is the kind of bond I encourage you to find with your apparel.


For more inspiration, grab a copy of GQ, or browse Pay attention to the initial reactions you have at seeing certain outfits or accessories. If nothing pops out at you, pass it on to an S/O, or someone whose perception of you that you value. If they get positive vibes from certain looks, chances are your other peers will too. And it’s those good vibes you’re after; they’re what form a positive image of you in others, making it easier to communicate with them, attract them, influence them, befriend them, gain their trust or support and generally succeed at interaction and life.