Winter cycling can be brutal, especially when trying to keep your head warm without compromising the fit of your helmet. I've spent countless rides trying to find the perfect balance between warmth, comfort, and safety. It's a challenge many cyclists face, and I'm excited to share my experiences and what I've learned along the way. Finding a good winter cycling beanie is key for staying comfortable.
For years, I struggled to find a beanie that would fit comfortably under my cycling helmet. Either it was too bulky, affecting the helmet's fit and safety, or it wasn't warm enough, leaving my ears freezing despite my best efforts. I tried thick wool hats, which were too bulky, and thin cotton beanies, which offered little to no warmth. I even attempted using scarves, which were a complete disaster, constantly slipping and obstructing my vision. It was a frustrating cycle of trial and error.
One particular ride stands out in my memory. It was a particularly cold morning, hovering just above freezing. I wore a standard beanie, thinking it would suffice. Halfway through my ride, my ears were numb, and the beanie had shifted, pressing uncomfortably against my forehead. I had to cut my ride short and head back home, thoroughly defeated. That's when I decided to seriously research and find a better solution.
After much research and experimentation, I finally found a few options that worked wonders for me. These solutions not only kept me warm but also ensured a comfortable and safe helmet fit.
My first discovery was merino wool beanies. I found that a Buff merino beanie did the trick perfectly. They are incredibly thin yet provide surprising warmth. The material is breathable, which prevents overheating and keeps sweat at bay. Plus, merino wool has natural odor-resistant properties, which is a huge bonus for long rides. I found that merino is definitely the way to go....warm when wet and won't stink!
During a ski equipment sale, I stumbled upon a stretchy insulated balaclava hood. This has been another fantastic find. It covers my entire head and fits snugly around my neck, offering excellent protection from the wind and cold. The best part is the stretchy fabric flap that can cover my nose and mouth for extra warmth, or be pulled down under my chin when not needed. It's incredibly versatile and comfortable, especially on those extra-cold days.
Another solution I've found is using a merino ear flap hat. I have a small head, so I found one at Walz Caps that works great without messing up my helmet fit. Also, I found that if you have other caps you wear, a wool buff or two is my favorite hack. Put on normal cap, put on buff over it and double up (pull over ears). This layering technique provides adjustable warmth and works surprisingly well.
For those extremely cold days, around 0°C, I use a Gore C3 Beanie wind stopper. It’s a game changer. The windproof material blocks out the biting wind, keeping my head and ears incredibly warm. It's a bit bulkier than the merino wool beanie, but the added warmth is worth it when the temperature drops.

Speaking of style, I once saw a really interesting beanie. It was the "2018 Fashion Spring and Autumn hats beanies diamond beard pattern cap hip-hop Skullies gorro turban hat for women bonnet caps Beige" from WholeCustomDesign Bulk, and while I haven't tried that specific one, the design caught my eye. I could see how a beanie like that, with a snug fit, could work well under a helmet, especially if it's made of a thin, breathable material. I've found that Wholecustomdesign often has unique and well-made products.
Based on my experiences, here are some practical tips to help you choose the right beanie for cycling under your helmet: