I have to admit that I thought you were being facetious when you first wrote about not being "able" to be cycle chic. Sure, it looks civilized and elegant to ride in snazzy clothes, but I'd never heard of anyone feeling inappropriately dressed when wearing specific cycling gear, just the other way round.
But reading your post it sounds like you do feel judged for not wearing chic clothing when cycling. Is that really the case where you live?
I guess I can see someone being judged for wearing hotshot gear like full matching team kit all the time, grocery shopping and running errands, but not just everyday commuter wear like a yellow jacket and standard black shorts. I dunno, I just never viewed the cycling chic movement as judgmental, just a celebration of it being possible to look elegant while riding a bike. I feel I can co-exist with that ideal quite comfortably, grubby commuter clothing and all.
Winter riding is much less about badassery and much more about bundle-uppery. - malkin
1995 Kona Cinder Cone commuterFrankenbike/Selle Italia SLR Lady Gel Flow
2008 white Nakamura Summit Custom mtb/Terry Falcon X
2000 Schwinn Fastback Comp road bike/Specialized Jett