
Originally Posted by
GLC1968
I want to appear like a hip but mature woman. Finding that sweet spot between 'mom' and 'cool' without crossing into 'trying too hard to look young' is tough!

Toss in the company branded items (which are almost never 'cool') and you get a real challenge!
That sounds like me, except I don't need to wear branded stuff much. Can you get away with wearing just a button or a pin? Or a cap or something else small? Or maybe just carrying a tote bag or briefcase with the brand name prominently on it? That would give you a lot more leeway with clothes.
We have some branded stuff too that I hate, but wearing it is optional. I try to look professional when we're out travelling, but luckily in my line of work professional equates rubber boots and goretex jackets 
Anyway. The hippest mom - and new grandmom - I know at work is also a cyclist, and wears lots of knee-length, colourful dresses. Not frilly feminine ones and not closefitting sexy ones, but semi-fitted, artsy detail, fun Pippi-like dresses without looking childish. A bit like some of these: www.desigual.com. And colourful shoes and boots. She looks fantastic.
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