Many years ago I started working with a large fashion brand, doing PR for Bonobos for a brief amount of time. Before this I’d been some sort of weird mix of “guy in hoodie” or “guy in awkward suit,” and I got a few hints to upgrade to “guy whose pants fit” and “guy who managed to get a second date.” This isn’t to say women are judgmental creatures, moreover that no woman wants to go out with a man who looks like he just rolled off a tour bus after hauling amps for an hour.

Men grow up with the antithesis of the pressure of women. While throughout their teenage to adult lives women are pressured with endless judgment and forced cultural tropes, men can get by with a much smaller set of evaluations. Why? Because we don’t have to deal with makeup, jewelry and the basic societal expectation that we must be pretty at all times. In fact, we can look “good” dressed down. Yet how do men screw up this winning formula? Little mistakes, that’s what.

This counts for any guy. I’ve been 130lbs, I’ve been 270lbs, I’ve been 155lbs, I’m currently sitting at 175lbs, and I know for a fact when I wear stuff that fits me (or did in the past), and feels good to wear, I am a damn sight more attractive to the opposite sex and in general feel more confident! Here’s how to do it.

Guys, if you’re a size 40 but you wear 38s to prove a point? You will be uncomfortable. Your balls will feel like they’re in an airlock. Do you want to put your balls in an airlock?

Prepare to spend some money.
Before we start – How serious are you about this? If you’re not, post it on Facebook or email me at If you’re reading this I assume you’re okay with this idea, but good clothes cost money because they fit better (ideally), they look better (ideally) and they’re better-quality materials. This isn’t to say you have to jump to the $150 pairs of jeans or $200 button-downs, but if you’re used to spending $10 on a pair of jeans, you may have a bit of sticker shock.

I’d recommend if you wanted to totally renew your wardrobe setting aside anywhere from $500 to $2500. That’s a lot of money. I know. It sucks. But the result is longer-lasting clothes and ones that fit you properly, ones that make you feel good-looking even when you are not an AAA movie star with abs that can cut diamonds.

What’re You Looking To Buy:
-Three button-down shirts
-Two belts: one black, one brown
-Three pairs of shoes—one smart black, one smart brown and a casual pair (Depending on your style, loafers can work both ways, and you can find some reasonable deals between $50-150 in this market. Kenneth Cole, Cole Haan, Hugo Boss and the like all have great options.)
-Three polos
-Two pairs of good jeans
– A formal jacket, a casual jacket
-If you can, some colored denim or cotton pants—grey or darker blue
-Comfy clothes that you don’t give much of a shit in but can still look good—This can range from your favorite pair of sneakers with some jeans, a t-shirt and so on…
-Optional: A watch. Some guys like ‘em, some guys don’t.
-At least one suit. We’ll get to that, okay?

You have options:
-Go to a store like Nordstrom and try things on in the dressing room. Preferably do this with someone who knows what they’re doing, or alternatively go freestyle and just go on your own and trust in yourself.
-Buy a whole bunch of stuff from Zappos or another online store, return the ones you don’t like.
-Use a service like Trunk Club that ships clothes to your home after a consultation and then you send back the ones you don’t like.

Trying to save money? Try these:
-Nordstrom’s annual sale or Nordstrom rack.
-TJ Maxx, sometimes
-Consignment stores
-eBay, once you’ve tried them on in a store
-See if a buddy has a bunch of pants that he has grown out of or just has too many then steal those, or buy them off of him if he sees you trying.
-Rob a store.
-Start a clothing company.

Understand what “FIT” means and FORGET about sizes.
I own, I’d say, five pairs of nice jeans. One’s a 34×32. One’s a 34×32 slim. One’s a 35×32 regular. One’s a 34×32 relaxed. They…all fit very nicely and comfortably—One might even argue that they fit identically. More importantly, they’re comfy and look good on me. I once was a 32, but I put on some weight as I grew older. This felt like shit. I’ve had weight issues my entire life to the point that I will look at myself in the mirror and think I look fat regardless of what the scale, my girlfriend or mental professionals tell me. It sucks ass. But it has taught me some lessons.

When clothes “fit” that doesn’t mean that they are tight against you, form fit-ing. Furthermore, you are not a particular “size.” I used to be a 32. I wanted to be a 32. I have 32s that fit me. I have tried 35s that don’t. These are all vanity sizes anyway, because the actual size of your waist is way, way larger. Break the fallacy in your head that you “have to be” a particular size. Guys, if you’re a size 40 but you wear 38’s to prove a point? You will be uncomfortable. Your balls will feel like they’re in an airlock. Do you want to put your balls in an airlock?

Jeans and Pants
I’d really recommend you do not go cheap on jeans. At Bonobos they sell $100-128 jeans that I personally like, but have not tried in years. And their first pairs were a little more tight on my juevos than I’d like to admit. My favorites are J-Brand, DL1969 and Fidelity—and in all cases those fall between $150 and $200, depending on the pants. I also like 7 for All Man Kind, which you can find outlets for and they’re quite affordable. I like AG for non-denim pants.

If you have only worn Old Navy or Gap Jeans (which are perfectly fine jeans and I own a pair or two), and then try on and find your right size in the above, it is night and day. It’s like putting on a pair of sneakers after a pair of work shoes. They feel nicer, in a way I can’t describe, and they fit you.

Other pants should be the same, but also fall into the same category of total wackiness between sizes and brands. You will try AGs that fit like shit, then J-Brands that will feel amazing, then another pair of J-Brands will feel like crap. Don’t feel bad when this happens. Fashion is weird, clothing is weird and your job here is to clothe your body not hit a god damn tick box. Slacks, too, can be weird. I’d personally recommend either going the same route as above, getting custom work done (I’ll get to that) or just ignoring them and getting dark cotton pants.

Side note: Get a belt somewhere. These are so subjective, but get one that holds your pants up without constricting you.

Shirts of all kinds
The one thing you want to know with your shirts is that they neither show the shape of your belly or leave a giant billowing balloon by your stomach. They shouldn’t be super tight anywhere, but bagginess makes shirts look cheap, even if they’re expensive. 

I like polos because they’re comfortable and come in a variety of colors and fits. They’re fancier than a t-shirt, yet casual enough to wear in a variety of occasions. If you want to go fancier, I like Burberry, but they’re $150 each and you better really like polos. Don’t talk to me about $350 Zegna shirts. Get them from Vastrm or somewhere else that uses similar high-end cottons if you really care that much.

Another good trick is to use Banana Republic’s almost-every-Wednesday 40 percent off deal. I also really like Everlane, especially if you’ve got a belly. They’ll still fit nicely, they have a good return policy, the prices aren’t terrible and they’re easy to work with. Banana Republic is also pretty good for short-sleeve button-downs. These are good casual shirts. Never tuck them in. For long-sleeved button-downs you’re about to enter a world of unearthly pain, of such confusion and mystery that I cannot tell you exactly how to do it perfectly.

Everlane and Bonobos also have good casual button-downs, but let’s say it clearly: Denim shirts are weird. As are dark shirts, such as dark green or dark black ones. Dude, don’t buy a black shirt. A casual shirt can be worn, for example, with a pair of jeans and sneakers out to a party or a bar. You’ll look good but not overdressed.

I’d also recommend you go to a Brook’s Brothers, despite them being overpriced, and let them measure you up and recommend a shirt. They usually have deals.

Charles Tyrwhitt also has a good selection of shirts, but there are about three stores in the country. I like them because I know my size now.

Denim shirts are weird. As are dark shirts, such as dark green or dark black ones. Dude, don’t buy a black shirt.

Never buy a suit off the shelf.
Go to a local tailor and get measurements or go to their walk-in suit shops (Indochino has a few, but make sure to not fall into the trap of, well, buying from them directly unless they can match the website). Do not go to Express and buy a suit. Don’t go to Men’s Wearhouse, even though they’ll measure you. I am 100 percent married to the concept that the best deal in town is one of the many custom suit shops online—Indochino, Knot Standard, Black Lapel (though in my experience they run a touch tighter) and their ilk all provide a better deal with a better suit that will make you look way, way better. For cheaper. This is not an ad, this is from a guy who owns a fancy Zegna tuxedo and worked with several suiting companies, and knows how royally boned you will get.

You really only need one suit, maybe two if you think you’ll hit a funeral sometime soon. Black suits are for funerals. Get a grey suit, or a navy suit. You want to wear brown shoes with anything that’s not a black suit. For a grey suit, it’s hard to go wrong, but make sure you’re not buying a weirdly-patterned one. Finally, you don’t really need a three-piece suit, unless it’s a tuxedo. Also, tuxedos traditionally do NOT have belts, and require white patent-leather (shiny) shoes.

Custom suits are also great because you can build them up in bits. For example, that blazer you have with the suit can easily be pulled over a t-shirt and some jeans and worn to be smart-casual. Or those suit pants can fit with a button-down for a business meeting that’s less casual than one requiring a suit.

In conclusion.
Your own personal style is something you will find eventually, and one I can’t personally remark upon because you’re you. The best way to look at it is to work on what fits you first, get comfortable in that, and slowly build up to what you think “works.” Remember that whatever you do, don’t try and dress like someone else unless you feel comfortable looking like they look. If you’re forcing yourself into someone else’s mold, you’re likely not going to feel good—and faking it until you make it is a suicidal strategy.

Photo Credit: Twenty20/@JenSosa

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