Yea but not young bums..
Then, you just look like a lazy bum, unable to afford modern clothes..
A lazy bum could never keep a closet of nice older clothing, only people who really care can do it.
Anyone who dresses nicely and presents themselves well looks fashionable. I can always tell if a woman is wearing older items because nice clothing and shoes are not available in current fashions.
No, it looks great even on many 40 and 50 +