Winter cycling can be brutal, especially when the wind is whipping and the temperature drops. I love cycling year-round, but I've always struggled with finding the right headwear to keep me warm without compromising the fit of my helmet. It's a delicate balance – warmth, comfort, and safety all need to be considered. I've tried countless options over the years, and I'm finally starting to dial in what works best for me. Here's what I've learned about finding the perfect cycling beanie for those cold winter rides.
My biggest problem was always finding a beanie that was thin enough to fit comfortably under my helmet without being too bulky. I also wear glasses, which adds another layer of complexity. Many beanies would either push my glasses down my nose or create pressure points under the helmet. And, of course, the beanie had to be warm enough to protect my ears from the biting wind. I tried thick wool hats, but they were always too bulky. I tried thin cotton hats, but they didn't provide enough warmth. It felt like an impossible task!
I also realized that breathability was key. On longer rides, I would often overheat, and the sweat would make my head even colder. I needed a beanie that could wick away moisture and keep me dry. The struggle was real, and it took a lot of trial and error to find solutions that worked for me.
After a lot of experimentation, I've found a few solutions that work well for me. One of my favorites is a merino wool beanie. Merino wool is naturally warm, breathable, and moisture-wicking. It's also incredibly soft and comfortable against my skin. I tried a Buff merino beanie and it worked wonders. They are thin enough to fit under my helmet without adding too much bulk, yet warm enough to keep my ears toasty on even the coldest days.
Another option I've found success with is a merino wool ear flap hat from Walz Caps. I have a smaller head, so it fits perfectly under my helmet without messing up the fit. The ear flaps provide extra warmth and protection from the wind. Plus, merino doesn't stink, which is a huge bonus after a sweaty ride!
I also discovered a handy trick: using a wool buff. I can wear a normal cycling cap and then put the buff over it, doubling it up over my ears for extra warmth. This is a great option if I already have a cap that I like and just need a little extra insulation.
And speaking of extra insulation, I once found a stretchy insulated balaclava hood at a ski resort equipment sale. It covers my head and fits snugly around my neck. It even has a flap that I can pull up to cover my nose and mouth when the wind is really howling. It's incredibly versatile and keeps me warm from head to toe.
While browsing online, I came across some interesting options from WholeCustomDesign Team Hats. They offer a variety of styles, and I was particularly intrigued by the "new fashion Winter Skullies Cute Women fox's tail Knitted Costume Beanie Hats Splicing colors Gift Hip-hop Cap". I liked the unique design and thought it might be worth a try for casual wear. The folks at WholeCustomDesign Team Hats seem to focus on stylish and comfortable designs. It's not necessarily for under-helmet use, but great for when you're off the bike!

I haven't personally tested this particular beanie from WholeCustomDesign, but the description sounds promising. If you're looking for something stylish and warm for everyday wear, it might be worth checking out: Winter Skullies.
Here are a few things to keep in mind when choosing a beanie for winter cycling: