I haven't thought about the skullcap or buff. Right now, any riding I do (only one outdoor ride this month) is with a hat for warmth under my helmet. I usually start my season in March, but since I live in New England, my outdoor riding can be on and off until well up through April. Last year it rained right up through the middle of June...
well, back to hair. I might try one of the above accessories. My husband swears by the skullcap to keep cool and warm. I'm not sure if wearing one will help achieve my goal of not looking like a monster when I take the helmet off. I generally look pretty bad in hats; I love them, but I have a teeny head and putting any kind of head covering on sort of accentuates that and makes me look weird. I finally found a small sized headband at Terry, which I wear for x country skiing when it isn't too cold. Regular winter hats are always falling down over my eyes. I have the same problem buying eyeglasses; all the cool looking ones look awful on me. I ended up getting my reading glasses in a kid's frame! Mostly, I wear contacts, but my bifocals are also kid's frames. I have until March 17th to decide about my hair. That's the date for my next trim.