It’s a old joke that most people stop “trying” after they get married: stop trying to stay in shape or keep up with fashion. For example, a recent poll suggests that 25% of men gain significant amounts of weight after getting married. After all, you’ve landed your catch, right? You don’t need to fool around with all that nonsense anymore.

Until you get divorced, that is. Maybe you’re finding yourself newly single, and packing on a few (or more than a few) more pounds than you did on your wedding day… and on top of that, your closet’s looking less Urban Outfitters and more Sears casual section these days. You want to look good, and it’s not just about landing a hot woman; it’s about feeling good about yourself. But fashion is a river that keeps flowing whether you’re swimming in it or not, and if it’s been a few years since you actually had to think about it, it can be intimidating to jump back in.

Fashion Tips for Big Men 

I speak from personal experience, by the way. I’m 6’3” and weigh what I’m going to go ahead and claim is around 260 pounds, and I know the terror of navigating the treacherous terrain of style. But luckily, while the hip thing of the moment comes and goes, some fashion secrets are eternal…especially for big men. So I’ve compiled a few to help you get started.

1. Keep it classic.

Maybe you’re browsing around on Vice and looking at the way the cool kids are dressing in Williamsburg and Portland these days. You could rock a plaid shirt with a bow tie and a pair of jean shorts, right?

Wrong. There are two people who can make hipster fashion look good: Ryan Gosling and…well, no, really it’s just Ryan Gosling, and definitely not you. So you’re going to go for timeless, classic looks. A good rule of thumb: if the outfit you’re considering would’ve gotten you carted off to the asylum at any point between 1950 and now, it’s probably a bad idea. You don’t want to be this guy.

2. Keep it casual.

Maybe you belong to a generation that associates looking good with ties and exquisitely folded pocket handkerchiefs. While there’s nothing wrong with that, these days it can be overkill. (Plus you run the risk of being mistaken for the head waiter at the restaurant.) A good dark sportcoat over an untucked dress shirt and raw denim jeans is a perfectly acceptable look for going out these days, for a man of pretty much any age. Make sure your dress shirt has a flat hem, though; if it has “tails” or is of uneven length, it’s meant to be worn tucked in and you’ll just look sloppy with it hanging out.

You can’t ever go wrong with a nice pair of Oxfords or loafers, of course. But definitely stay away from big, flashy sneakers, unless you are actually a member of Run-DMC.

3. Not too casual.

There is nothing sadder in the world, in my opinion, than a fat guy in a polo shirt and Sansabelt khaki slacks pulled up to his belly button. It’s a look that tells the world that you’re not afraid to admit you spend your Saturday nights playing Magic: The Gathering with the other guys from the IT department.

If you’re going to keep it on the casual tip, nobody ever went wrong with jeans and a t-shirt. You’re probably going to want to go with sedate, darker-colored t-shirts; shallow V-necks are great for big men (they accentuate the length of your neck rather than the width), but deep V-necks will make you look like you’re trying too hard. Jeans should be dark, preferably raw denim, devoid of embroidered designs or, God help us, bedazzling. Wear your jeans around your hips — you’re not fooling anybody by yanking them up to your imaginary waist, and you look like somebody’s grandpa. And wear a belt, because the second-saddest thing in the world is a fat guy walking down the street trying to keep his pants from falling off his non-existent butt.

4. Avoid big and tall stores.

There seems to be some cultural consensus that if a man is heavy or large, he must enjoy dressing like he’s mentally challenged, or possibly a private detective from an 80s TV show. If you’ve ever set foot in a big and tall store, you know what I mean: soul-crushing and ludicrously overpriced Hawaiian and Cuban bowling shirts, floral-print muu-muus, tacky golf pants and t-shirts with “wacky” slogans like NOBODY MESSES WITH THE BIG DOG. If you didn’t feel like Chunk from The Goonies before you walked in, well, you do now.

Unless you’re morbidly obese, most major chains will carry a subset of clothing in your size. Old Navy, for example, is very good about carrying XXL shirts and jackets, and larger-sized pants. Burlington Coat Factory has an excellent Big & Tall section, although a lot of the selection skews towards urban-style stuff like Rocawear and FUBU; nothing wrong with that, of course, but it’s not really my style, personally. Your mileage may vary. But anything is better than walking out of a big and tall store with a George Foreman-branded shirt that makes you look like a Hialeah bookie.

5. To shave or not to shave?

At this precise moment in our cultural timeline, beards are in, in a big way. But it’s pretty much an all-or-nothing thing for heavy men. A full beard will hide your lack of a jawline and make you look masculine; a clean shave will show that you’re serious about your grooming.

Whatever you do, don’t try some kind of stunt facial hair like a razor-thin chin strap or a gigantic wax mustache. You won’t look daring. You’ll look like you just ran away to join the circus.

6. Jewelry.

Aside from a nice watch or a simple bracelet: don’t. Just don’t.

7. A new do, a new you.

Hair is tricky for big men. Longer hair tends to fit round faces better, and can give you that Game Of Thrones look, but you have to be a certain type of dude to really pull it off. Ditto a shaved head: do it right and you’re Vic Mackey from The Shield, do it wrong and you’re Uncle Fester. Your best bet is probably something longish, tousled rather than tightly-groomed: think current-period Seth Rogen. And, as with your facial hair, stay away from stunt styles.

8. Silk shirts, sharkskin suits, suspenders, leather dusters, fedoras.

See # 6. And seek psychiatric help.


Do you know any guys that need some fashion help?

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