I have worn some strange things while biking, mostly on RAGBRAI.
Bikini top, grass hula skirt and leis. That was hawaian day. Leopard top and skirt for jungle day. Gotta be careful with the skirts and not get them caught in the spokes. We had an Irish day and put shamrocks on everything. Where'd you wear all your stuff, pedalfaster?
Leather pants, leather bustier, leather jacket and biker boots for a Halloween ride.
Haven't done the commuter thing so no normal clothes that just seem a little different on a bike, no cashmere.