Winter running can be amazing – the crisp air, the quiet trails… but freezing ears? Absolutely not! I used to dread those first few miles when the wind would whip around my head, making me question my life choices. Finding the right winter running hat or headband became a mission, and I'm excited to share what I've learned.
Like many runners, I struggled to find a hat that kept my ears warm without being too bulky or interfering with my headphones. I have a larger head, so finding a hat that actually fits comfortably was another challenge. Beanies often felt too tight, squishing my ears and making it hard to hear. And forget about wearing a ponytail – most hats just didn't allow for it.
One of my biggest issues was keeping my earbuds in place. The slightest movement, and they'd pop out, especially when combined with a hat. It was incredibly frustrating to constantly readjust my headphones while trying to focus on my run.
After much trial and error, I discovered that a combination of different headwear options worked best for me, depending on the weather conditions.
My first breakthrough came with headbands. I now swear by them for milder winter days. I love how a headband covers my ears perfectly without overheating my entire head. Plus, I can easily wear a ponytail. I found that fleece headbands are particularly comfortable and effective at keeping my ears warm. They don't squish my ears as much as a beanie, which is a huge plus for me. If you're looking for other options, check out the category for more styles.
Another option I've come to rely on is a buff. I simply scrunch it up in a headband style to cover my ears. This is great because it's so versatile – I can adjust the thickness depending on how cold it is. It also works well with my Shokz headphones, providing a comfortable and secure fit. This method has been a game-changer for me over the past few years.
When the temperature really drops, I reach for my Smartwool Intraknit headband. The wool provides excellent insulation, keeping my ears toasty warm even in freezing conditions. I also appreciate that it's not too bulky, so I can still wear my headphones comfortably.
I also tried using a gaiter scrunched up like a headband. This works surprisingly well and keeps my headphones secure and my ears warm. It's a simple and effective solution that I've been using for years.
While the above options are great for performance, sometimes I want something a little more fun and stylish. That's where the Cartoon Bear Ear Novelty Hats from Wholecustomdesign come in.

These aren't just cute; they're surprisingly practical for winter activities. The balaclava design provides full coverage for my head, ears, and neck, protecting me from the wind and cold. It's perfect for cycling, skiing, or just a casual winter run. I was initially drawn to the design, but I've been impressed with how warm and comfortable it is. Plus, it's a conversation starter! You can find it at Wholecustomdesign. The warm mask is an added bonus!