Look, I’ll be honest with you, when I first started winter cycling five years ago, I showed up to rides looking like I was about to summit Everest. Too many layers, not enough thought, and way too much sweating. As a fashion editor who happens to be obsessed with cycling, I’ve spent the better part of my 35 years figuring out how to look good while staying functional. And let me tell you, winter cycling gear has come a long way.
That’s exactly why I fell in love with cycling apparel from OrionRide. These guys get it, they combine vintage-inspired aesthetics with modern technical performance. Their philosophy revolves around freedom, adventure, and that deep connection to nature that every cyclist craves. Plus, their designs don’t make you look like a walking billboard or a traffic cone. It’s gear that works as hard as you do, whether you’re grinding through a freezing morning commute or hitting gravel trails on a crisp Saturday.
1. Start With a Breathable Base Layer
I’ve learned that winter cycling comfort begins with moisture management. Sweat is your enemy; a clammy base layer will chill you faster than the wind. I normally go for something that hugs close without feeling restrictive. Breathable synthetics work best for me and set the foundation for the rest of my outfit.
Sometimes I’ll swap in one of my favorite OrionRide tees, especially their cycling shirts, when I want a lighter, sport-casual base layer that still wicks moisture surprisingly well.
2. Add a Thermal Mid Layer for Warmth
After the base layer, I reach for insulation. This is where I like to have fun with color, graphic prints, or textures. A mid layer should feel cozy without trapping too much heat. OrionRide’s gear always nails that balance, especially their long-sleeve options.
On gravel days, I’ve even layered with a gravel shirt for a bit of rugged warmth. It adds just enough thermal comfort while keeping the vibe casual instead of overly “pro-cyclist.”
3. Top It Off With a Weather-Resistant Jersey or Jacket
Winter rides demand a barrier between you and the elements, windproofing is a must. I look for jerseys that give me mobility while still blocking gusts and trapping warmth. Water-resistance is a bonus, especially when the sky looks questionable.
If I know I’ll be hitting mixed terrain, I’ll grab my OrioRide gravel shirt cycling as an outer layer. It’s become my go-to for unpredictable winter days, especially on sloppy gravel routes.
4. Prioritize Smart Storage for Ride Essentials
In the winter, I always carry extras, gloves, a lightweight buff, or even chemical warmers on sub-zero mornings. That means I rely heavily on jerseys with well-designed back pockets. They keep everything accessible but stable while I ride.
That’s why a cycling shirt with pockets is non-negotiable for me. The right pocket layout lets me stash snacks, gloves, and my phone without weighing me down.
5. Don’t Forget the Fun Layer, Style Still Matters!
Even in the winter, I like my gear to reflect some personality. Whether it’s bold prints or island-inspired graphics, style boosts my mood when the weather is bleak. Winter doesn’t have to be all navy and black.
I’ll often throw on a hawaiian cycling jersey under my jacket. It stays hidden most of the time, but I know it’s there, and that little spark of color just makes the ride better.
The Bottom Half: Don’t Neglect Your Legs
For cold weather, I need durability, warmth, and flexibility. I’ve shred-tested plenty of shorts and pants, and OrionRide’s MTB lineup is surprisingly winter-friendly. Paired with thermal tights underneath, they’re nearly perfect.
The men’s mtb shorts give me wind protection and a rugged shell without sacrificing movement.
When the temperature drops below freezing, I switch to a long sleeve cycling jersey layered under a shell, my ideal combo for warmth and breathability.
On days when I’m hitting downhill trails in winter (yes, I’m that guy), I rotate in a downhill jersey for extra durability and airflow.
Don’t Skip the Final Layer: Cozy Warmth Post-Ride
Once the ride is done, nothing feels better than a warm pullover while I decompress with a coffee. OrionRide makes some of my favorite casual layers, perfect for thawing out.
My go-to is a bike sweatshirt with a soft interior that warms me up instantly.
And when I want something extra soft for the ride home, I pull on my knit bike sweatshirt, a cozy classic.
Winter cycling isn’t just about surviving the cold, it’s about finding the right layering formula that makes you feel confident, warm, and ready to enjoy the ride. With the right mix of breathable base layers, smart mid layers, and stylish outer pieces, you can tackle any chilly route with comfort and personality. For me, OrionRide has become my winter cycling wardrobe MVP, blending style and performance better than most brands I’ve tested.
