This is Isaac:
I met him on the corner of 3rd and Folsom, and I stopped to compliment him on his short distressed denim coat (not just a jean jacket). Nice fashion choice, Isaac! His bicycle is also incredibly cute. Isaac also dons a matching blue cap.
I think the word for men in hats would be dapper (in my humble opinion). But it has to be the right hat for the man. For example:
This fellow in plaid shirt and black hat and matching black hi-tops on 16th and Guerrero, and...
this young chap dressing up his sporty look with a brown hat seen on Bryant and 16th.