Occasional matching is nice. Worrying about matching all the time is for 'sissy' or those with low self-esteem.

We, strong women can defend our fashion choices with one heavy sigh and long stare at the person. Honestly, if someone suggested that my sunglasses must match my watter bottles or something like that, I would laugh for a very long time. It is great to have your own style and choices which our not dictated by some 20 yo clerk in the LBS. Sunglasses are too finicky to care about color; they must match your cheekbones (we don't want additional wrinkles from too large sunglasses or from too small ones), must match you head size and must not give you headache after a day wearing them. That is important.

Honestly, I wear black with occasional red accents because I like red. My bike is silver and black. Recently I got a red chain because I just thought will be funny. But I will hapilly wear screaming yellow jacket in cloudy/rainy conditions and yellow screaming helmet because it MIGHT save my life. I don't care if I don't look as professional biker. It is actually even more fun to look like someone who just start biking and then blow fast around all the 'matchy' professionally $1k-spent-on-outfit. I never forget to remind them that they have 30 (or 20) gears and are still slower than me on a fixie. "Sorry, I have a fixie, I must pass you since I am FASTER than you!"