Featuretile, my bike clothing experience was a bit like yours. DBF said "Yeah, you need shorts" and dragged my butt to Performance for a cheap pair (all I was willing to buy at the time.) The helmet was not an issue--I'm not dumb enough to ride without one, and even if I was, my BF would never let me near a bike without one.

A couple miles, I could do without all the spandex and a jersey. Never dressed up like that, though. I can't walk around and look like that. I like the idea of a "casual bike wardrobe" for jaunts to the coffee shop or to class and the like. I need the wicking fabric-- I could sweat for England.