Sorry to be the voice of contention here but this sounds like the type of question only asked by people who never spend time in urban environments. The beauty of city living, compared to small-town USA, is that no one gives a damn what you look like. On my sidewalk on any given day I have Hasidic Jews (think Amish black traditional garb), yuppie joggers, cops, doormen, delivery personnel, postal workers, single moms, the can-lady (big cart full of 5 cent cans), Wall St. brokers, soldiers, teachers, lawyers, accountants, athletes, skaters, drug dealers, drug users, drunks (besides me), kids, teens, elderly, etc.

The point is there's not an "urban dress code". No one is going to see you walking through midtown with your Kelty backpack full of firestarters and fishhooks and yell "Look! There's someone without True Religion Jeans!" Avoid the tacti-cool look of Brigade Quartermaster crowd and you'll be fine.

And if you ever really lost in NYC just look me up and I'll give you a safe place to stay. ;-)