Yes and no.
I'll ride all my bikes with normal clothing when commuting or popping to the shops.
However when I properly go riding, the bike and clothing have to fit eachother. You just can't wear Retrobike clothing when you ride a 2011 bike.
Similarly, when I wear a jersey that says "WARNING : I have disc brakes and know how to use them" on the back, there's no way I'll ride a bike that uses cantilevers.