Like you Trek and many others probably, even when I wear cycling gear, I'm not matching colours, sleekness at all:

Whatever is clean, is my motto.

I wear slightly baggy dark green windpants for rainy/cold weather, whatever cycling jacket is right temperature-wise. One of the jackets has an acrylic black paint stain which I've given up scrubbing away. I got my hands dirty from art class. But why throw away the jacket? Still serviceable after 8 yrs. I do make my clothing last, both cycling and non-cycling stuff.

My cycling shoes are narrow mountain bike like shoes...I just choose a style that's not too wide so I can toe-clip in (yea, I'm still that geeky!!). I ride an upright hybrid bike (no one can ever accuse of me not being ordinary cyclist)..

I wear red framed plastic cycling glasses. Other times I've had bright blue or silver. I love wearing flashy glass frames that don't match with anything. It's just FUN to wear them.

There have been times my jersey is sticking out past length of my vests or jackets. Oh well, that's the price of being short/petite.

I actually consider wearing cycling gear, an opportunity to be wearing stuff way flashier and more fun (like some designs and colours of jerseys), that I would never wear indoors colour-wise. I know that I can wear bright, neon colours well outdoor against my natural colouring. So strangely, I actually do feel more "chic" than dull me indoors.