Most men look terrible as they get older because they get fat - when you get fat, your arms don't grow as your belly grows so shirts rumple in odd because the proportions are wrong. Then they couple that look with some shapeless jeans that look like they have just robbed them off a homeless person.
It must be much harder for larger men to buy clothes that fit properly than us larger women. I'm a UK size 16-18, and shop almost exclusively at stores that cater for larger sizes because the proportions of the clothes in these stores are right. Simply upsizing a size 8 pattern to a 16 doesn't work because the overall proportions change. It's pretty easy for me to find clothes that fit properly, including jeans, but it must be much harder for larger men. I can't think of any store which caters exclusively for their clothing needs.
I'm 44, and lately when I've been shopping with my teenaged daughter I've asked her point-blank whether I'm too old to wear a particular item of clothing. This is when her brutal honesty comes in handy.