I've bought my share of beanies that itched after ten minutes, slid up over my ears, or vanished somewhere between the car and the office — so this year I finally kept the ones that actually fit. This is my pick of the best winter beanies for men under $30: warm winter hats and knit beanies that stay put on cold, windy mornings without scratching or squeezing. They're for men who want a warm beanie that actually fits and doesn't itch, whether you're walking the dog, heading to work, or standing on a freezing sideline. Every one is under $30 — which one would you reach for first? As an Amazon Associate, I earn from qualifying purchases.