The Style Guy Answers Your Most Frequently Asked Menswear Questions

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Style Guy is a pretty great gig. The benefits are decent—medical, dental, tailor-al are all covered. I get most fashion holidays off: Paris Fashion Week, Labor Day, Prince’s birthday, etc. And you guys are always polite with your sartorial insecurities, whether you’re tweeting at me or stopping me mid-green tea order. But every job has its negatives. And this—this exercise in answering the entry-level questions about men’s style—is the toughest part of the work. In fact, it’s an occupational hazard. Why? Because I don’t want to tell you exactly what to do. I want to tell you how to do what you want to do. I hate the idea of some manual of unbreakable style rules. I’ve also, in my short tenure as Style Guy, answered all of these questions a trillion times. But what I hate more than anything—what I swore an oath never to do—is to leave you hanging. So, here (with my editor’s gun to my head) is a lightning round of the questions I get the most. Hopefully for the last damn time.

How far should my pocket square peek out?
Half an inch at the most. Always style the pocket square with your jacket off. It’ll give you a better perspective.

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…and the cuffs of my shirt?
Half an inch, too. Especially if you have monogrammed cuffs. Showing them off is doubling down on the douchey.

Where should the bottom of my topcoat hit?
Your knee. Give or take a few inches in either direction.

…and the bottom of my pants?
Pass! (I get one pass, right?) It’s totally up to you. I have handsome ankles, so my pants are usually cropped.

What things should every college guy have in his closet?
I went to Morehouse College, where students get dressed up for class. I expect the same from you. Nice dark jeans, thick cardigan, respectable sweats, and a navy suit. (And no, the suit isn’t optional.)

How do I pull off a T-shirt under a suit without looking like a club owner?
Thin solid T-shirt. Slim, soft-shouldered blazer. Keep things tonal. (Black on black is an easy way to start.)

How do I pull off a shirt and tie without looking stuffy?
A neck tattoo. Easiest way to never look stuffy. A slim tie is another, non-permanent option.

I can wear white after Labor Day now, right?
(Seriously, this is painful for me.) Yes, dude. Do it.

Belt or no belt with a suit?
No belt. If your pants need a belt, they’re too big.

I’m going to a black-tie work event. It’s important that I make a good impression. How can I make my tux even bolder?
I say don’t. But only because if you’re asking the question, chances are you’ll feel self-conscious the entire night. Just find the sharpest black tux you can afford.

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What tie knot should I use?
The simple four-in-hand. Please stop it already with the big, fat Windsors.

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