I have always had this problem too! I refuse to ski without a helmet, but always get sweaty and my hair is a mess by the end of the day. I just don't get how some people manage to pull off perfect hair after wearing a helmet. Here are a few thoughts:
- I concur, Athleta makes cute hats and some that have pony tail holes.
- Wedze,
https://www.wedze.com/en, makes cute hats. A friend of mine just bought my one for xmas with a cute pom pom on top and I love it- I too don't think some winter hats look good on me, like regular beanies, something about my forehead & lack of bangs just don't work. This one is super soft and looks pretty good.
- I'd also encourage checking out Etsy for a funky vintage 80s/90s hat or a homemade one. I bought this one on Etsy last year and get tons of compliments on it. It has a pageboy-style brim and though it's knit, it's a chunky knit so it breathes well:
Last, two seasons ago I left my neck gaiter at home and had to purchase a substitute at the mountain. I bought a buff, which is light but very effective at blocking out wind and BONUS can double as a beanie if we stop mid mountain to warm up or grab an adult beverage. I really hate having to take my helmet off with nothing else to put on my head, so it's nice to have this option in a pinch:
https://www.buffusa.com/sports/
On a separate but related note...... I've found it disturbing, whilst watching the Sochi Olympics, that some of the women (i.e. slope style competitors) wear a hat under their helmet, and their helmet essentially pushed back on the back of their head loosely so as to not mess up the underlying hairdo. God forbid that you crack your head open and have a hair out of place!!! Anyone else notice that??