How can a bigger guy dress nicer?

I have a friend - and no, this isn’t one of those “the friend is really me” deals - who’s about 50 lbs. overweight, but he’s pretty tall, which helps balance it out somewhat. Still, not a slim guy.

He’s 30, killer personality, one of the funniest people I’ve ever met in my life, quite handsome when he maintains himself (he tends to get depressed and let himself go sometimes), but he dresses like a 14-year-old. All jeans all the time (which is fine with his job) and band t-shirts.

I’m trying to help him class it up a little bit in hopes of re-entering the dating scene, but he’s very resistant to new clothing and so on. As he jokes, “I don’t have adult clothes.”

How can a fat guy dress better?

I’m of the opinion that most of the fashions that fat guys do to try to look nicer, such as the old “open button-down shirt worn over the t-shirt” just make them look bigger and sloppier.

What direction can I help push this guy in, purely on a casual “hang out” clothes level, to help him look better and more appealing?

Slacks and shirts without logos should do fine. He just has to make sure they actually fit well instead of being too big or too small.


He’s 30, so I assume the best way is to let him make his own decisions about the clothes he buys and wears.

Unless he’s actually told you he’s ready to date again and explicitly asked for your advice, but I’m guessing that’s not the case.

Here’s a few pictures…is this the kind of silhouette we’re talking?

Don’t horizontal stripes tend to be slimming? And dark colors?

I’m pretty sure, too, that he should avoid vivid patterns (damn…if only I kept those back issues of Men’s Health, with all the fashion advice).

And, of course, wearing clothes that fit properly is key.
Of course, all of this advice is moot if it isn’t how he wants to look; far better to be hated for who you are then loved for who you aren’t.

Pressed pants, not jeans. Simple belt. Solid bright colour button down shirt, tucked in and done up except for the top button. Casual leather shoes, non-scuffed. Non-athletic socks that don’t clash. Neatly trimmed hair, clean shave, clean fingernails. Smile.

Actually, that is the case - he specifically came to me asking for this advice.

Sounds to me like his clothing is a reflection of his personality. To force him to dress different would be akin to ‘false advertising’!

Has he explicitely asked for your help in (a) getting a girlfriend and (b) changing his style of dress?

He’s actually not even as big or round as those guys. Besides, there are so many things wrong with those four pictures!

From L to R:

Pleated khaki shorts?! Ahhh!
Not bad, but the white shirt makes him look positively huge and tucking it in doubles the effect.
Top right: lighter colored top makes him look bigger, while the black pants make him look even smaller from the waist down, further creating a “Humpty Dumpty” effect.
Bottom right: there are so many things wrong with this one. “Shirt over shirt” just looks sloppy. Too-short khaki shorts look ridiculous. This guy’s never going to get laid.

A) yes, and B) yes.

I agree with everything that Muffin said. The quickest way to start looking better is to ditch the jeans and t-shirts.

Try and find casual pants that aren’t pleated in the front. IMO almost no one looks good in the pleated trousers and big guys even less so.

Ditch the sneakers and go for a nice casual loafer or any casual leather shoe. No white socks please.

If he wants to look more laid back leaving the shirt tail out seems to be OK these days and tends to elongate the torso and minimize the gut if he’s got one.

Good luck to your friend and try and convince him to post before and after photos.

Better yet, nominate him for one of those make-over shows like What Not To Wear or Queer Eye for the Straig Guy.

I might say go for small changes if he’s unsure at first. Trade in the band T-shirts from some plain CLEAN UNRIPPED undershirts, buy some button down shirts in solid colors or not-ugly patters and tell him to button his shirt. Get some decent shoes (not-sneakers). Shave. Trim eyebrow, ear and nose hairs. I think he can keep the jeans if he’s really uncomfortable in slacks, but he should have something on hand for nicer events.

Heh, okay I agree with you that there are some things I would change about each of those looks, BUT … do you want to date him? :wink: You didn’t mention whether he wants to date men or women, but from my viewpoint (as a woman), any of those outfits are a step up on the “adult clothing” scale from jeans and a t-shirt.

Other thoughts:

What is he wearing on his feet? This is so critical. Good shoes make just about any outfit look better. Nice quality leather shoes are a plus, like Docs or other casual footwear. Sneakers, of course, dress an outfit down. Tevas or other sporty sandals likewise, unless he is on a date where he’s actually engaged in a sporty type activity.

I think pressed white linen shirts look good on men of just about any size. I would suggest not being afraid of white or light colors – I know there is a belief that they make people look even larger, but in the real world, everyone knows how big he is regardless of what he is wearing at the moment. Bright colors are not terrible, either. The one area I would be wary of is prints – either large or small. Especially on a larger man, the print can seem like just too much of whatever it is.

Untucked shirts are becoming more acceptable at more places these days, and I think this is often a look that is comfortable for larger men, BUT (I cannot emphasize this enough) if a shirt is untucked, it must be especially neat. No frayed hem, or those thin fabric shirt hems that “roll” at the bottom.

V-neck sweaters over solid color t-shirts are very in right now (personally I’m not sure where I stand on this issue, but they’re all over the place) and that’s a look that translates well to a larger-size man. The nicest ones are in natural tones, tan, stone, etc. I would also add that a cashmere sweater is especially nice to touch (if he offers his arm to a date, for example). The V-necks are out there in pullovers and button-downs, I would lean toward a pullover for your friend. Button-downs will emphasize a tummy too much.

Get him a decent haircut, too, if his is lacking. That can have an amazing slimming (or aging, or de-aging) effect, and it’s a $20 investment.

Since you mentioned a “casual, ‘hang out’ clothes level,” I think dark wash denim jeans in a straight cut would be nice, especially if his current jeans are on the tattered side.

Nonono on the shirt untucked! It just makes big guys look bigger, because it makes their waistline disappear.

Shirt tucked in. And a belt.

If he complains that this is “uncomfortable”, he’s wearing the wrong size. Tell him to go someplace that sells good pants and has a sales staff (i.e., not Target or Sears or something), and ask them to help him find a pair that fits.

But, seriously, that “shirt not tucked in” look goes well on thinner guys, but it’s on the way to muumuu-land for bigger guys.

If wearing a shirt un-tucked, it should be one designed for that with a stright hem, such as a Guayabera or Hawaiian shirt.

If dressing very casually, consider mesh shoes rather than athletic shoes, and for god’s sake, never Croakies.

He should be thankful. I’m a fat guy. My female padlling crew dresses me in a pink T-shirt with a beanie.

Which I have to zip home to change into right now, for we’re dancing in the park tonight, and racing the big canoes tomorrow!

How tall is ‘pretty tall’? Do be aware that the BMI is only a guideline and doesn’t work so well for very tall people. I’m 6’3" and 17 stone (238 pounds) and want to lose 2 stone. This will still leave me in the overweight category, but the BMI table I consulted said I should be okay at 156 lb. A loss of 82 lb. Sorry, no way. I was far too unhealthy at that weight.

Is his extra weight flab or muscle? If it’s flab like me, and thus on his belly, then I suggest good shoes, chinos, a jacket, and exercise.

Get him a Land’s End men’s catalog. The have everything from business to casual to sport wear, in all sorts of big & tall sizes. The clothes are reasonably priced and the quality is decent. Stuff he buys from them will hold up pretty well over the years. It’s mostly ‘classic’ stuff that will be in style for the next ten years. So buying some basics now means he won’t have to replace his wardrobe next year.

But the real point of the catalog is to give him a visual reference for guys of his build and age. You could go to too but the pictures are better in the catalog. If he browses through a couple of the men’s catalogs he’ll get a chance to see what lots of different pieces of modern casual clothing looks like and think about how he can work that into his life.

A good haircut, decent pair of jeans and a soft polo or Henley shirt won’t feel all that different than his current jeans & band shirt but it will look noticeably better.

No, horizontal stripes accentuate the bulges and contours.

All these years I thought you were female.