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?