It really has a lot to do with where you are too. Commute on a fixt to work or the grocery store in a team kit and you’re a total dork. Show up to USCF sanctioned road race in your black and white cammy cut offs and Black Flag tee shirt and your even dorkier.

I where these cheap bike under shorts from Trek under my cutoffs for commuting mostly cause whity tighties suck after about 20 ft of riding and they tend to hold the package in. Any old shirt will do. Usually what ever is on the floor and relatively clean. When I train and race crits in cat 4 I wear simple either two tone or plain solid colors with no advertisements. If I get good enough I'd love to wear the advert of my sponsor but as for now I aint gonna wear a team kit that I am not a member of and I sure aint gonna advertise for free.