Depends where you live and what kind of places you frequent....maybe where he's at that would be acceptable.
The best is when fellas like that one try to look "serious" and "official" all the time. They wear "expensive" looking clothes, expensive watch, shoes out of aligator skin, etc... I could afford all of that, brands, etc.. tho' I like to look like I'm just out and about, care free, urban-style. That suits my personality very well. Not to repeat that if you guys are really serious - it's baffling, as it's normal look in Europe (unless you are are 40+old dude AND look like it.. Then a casual polo or shirt is the way to go. ).