I am often asked for style advice. This is unsurprising. Not because I dress cool or look good. It’s because I work at GQ. Giving style advice is an inherent part of my job. Strange then, perhaps, that I fundamentally don’t believe in giving style advice. I know a lot about clothes and wearing them. But when it comes to giving advice—specific, prescriptive advice—I’m not just disinterested, I am diametrically opposed. Sorry. I want to help you on your journey toward a more fulfilled and stylish life, but I’m not going to give you a set of rules to live by. Even if those rules actually exist, I don’t know them!

Typical style advice follows certain recurring patterns—how should something fit, what to wear it with, and when to wear it. For menswear in particular, there is a long history of rules, based on standing traditions of tailoring and uniform dressing. This magazine has made many significant and correct contributions to that history. And still does! But I believe there is an alternative path to style nirvana—one that for some might be easier and more natural.

My philosophy in general is that style advice is a kind of fallacy. Not that all style advice is bad. It can be good, smart, and useful. (For the record, Glenn O’Brien’s very excellent archive of Style Guy advice columns still holds up, but I’d argue that he could have been writing advice about auto repair or landscaping and it would have been just as entertaining and enlightening.) It’s simply not the way I think about what I wear.

For starters, most style advice is typically based on the general premise that if you wear the right clothes in the right combination you will look and feel better. It starts with the outcome, not the clothes.

Style advice that does start with the clothes—explaining how a thing should fit or what you should wear it with—tends to take a rather one-dimensional approach to clothes. That word should is the issue here. It indicates a certainty and rigidness that comes from a place of insecurity and self-doubt. Don’t be a should man. Be a could man! Cultivating a deeper understanding of the clothes you own and wear will eliminate the should from your life. When someone is searching like this, trying to find the answer to some outfit riddle, it’s not because they don’t know the answer. It’s because they don’t understand the question. Good clothes don’t leave you wondering how you should wear them.

A lot of style advice also boils down to: Tell me what to buy. Fair enough. Shopping can be a pain. Browsing e-comms is bad for the soul, and shopping in stores brings its own set of existential problems. Figuring out which things in your closet are complementary and which things clash is all just part of the process of owning, wearing, and becoming familiar with your stuff. You don’t need someone else to tell you what to do—what you should do. You just need to put that shit on and go outside and see how it goes. Worst case scenario, it didn’t work out and you won’t do it again. But if you aren’t buying bad clothes, if you only own things that you like, if you’ve done the due diligence of being considerate about how and where you spend your money, it’s hard to go too far wrong. The cool part about having good clothes is that you get to try wearing them in different ways.

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