The Original What Not to Wear (on BBC) “redid” a big guy–actually, the husband of a previous lady “redo.” (Apparently, I wasn’t the only viewer who reacted poorly to his condescending approval of her new look. As in: “You should talk, Lardo!”)
His weight was mostly in his belly. So he chose to cinch his belt tightly around his rather slender hips–under the belly–then tuck in his baggy tee-shirt. Thereby exaggerating his worst feature. The girls got him into layered tops, such as a vee neck sweater (in a thin knit) over a tee-shirt. Warm weather equivalents would be the guayabara-style shirt. (Details would vary, depending on the exact body type.)
The guy was a contractor, so his work outfits were informal. He switched out his juvenile athletic shoes for equally comfortable black leather trainers. Faded denims were dumped for well-fitting dark jeans. Generally, he upgraded to better fabrics & flattering colors. And brushed up his grooming.
There was enough left in the clothing budget for one suit, tailor made in London. Which is guaranteed to make any man look his best.
He doesn’t have to give up on jeans, but they must a) fit, b) be in good shape, and c) be a decent color or wash. The crotch of the jeans should be at the crotch of his crotch, and there should be some detectable ass-contour. He shouldn’t be busting out of them in any direction, and no gymnastics should be required to get into them, even when freshly washed.
One of the big things that prevent people from improving their image is being afraid to leave their rut. When (/if) they go clothing shopping, they only look at the kind of stuff they’re already wearing. It’s very important for your friend to look around and try some things he wouldn’t normally wear. The whole point of fitting rooms is that it’s okay if the clothes you try on look terrible on you – nobody else has to see! And sometimes you might find that the shirt you thought was too bright or whatever actually looks good on you.
He should pay attention to what other people are wearing and how it makes them look, especially if he spots a guy who has a build like his. This is one of the easiest ways to avoid some fashion don’ts, or pick up some new fashion dos.
Also, white socks are for wearing with sneakers only. Trust me on this. And your socks should not show when you walk if you’re wearing full-length pants. An inch or two difference in pants length in any direction can make a bigger impact on appearance than you might think
I think that slim fitting, contoured button-downs can be a really good fit for a big guy and minimize the belly. Other than that, I second the layered sweater and dark jeans look.
Gestalt
Presumably he wants to date adult women, so he may want to reflect on the merits of leaving his “comfort zone” (= rut) in this area. Dressing with a bit more style tends to enhance attractiveness and garner a few compliments here and there. The rewards are worth the effort to overcome ones’ reluctance.