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3 min readI LIVE IN New York, and winter has officially settled in. Temps dipping below 40 degrees is not exactly my favorite thing, especially since I commute to the office three days a week, walk everywhere, and still make it to the gym after work. In weather like this, layering is optional. My outfits need to survive a 10-minute walk to the train, overheated subway platforms, drafty workspaces, and whatever weather whiplash the day throws at me. After years of testing clothes for a living (and freezing in the wrong ones), I’ve landed on a layering system that actually works in real life. Whether you live in a cold region or need clothes that can handle long days spent moving in and out of the elements, here’s how I do it.
Start With a Base Layer
This is the most important step—and the one most guys get wrong. Your base layer shouldn’t feel like underwear. It should be something you’d happily be seen in once the coat comes off.
For me, that’s usually a heavyweight tee, a slim merino long-sleeve, and a lightweight thermal with structure. I avoid anything too flimsy or overly athletic unless I’m going straight to the gym. Stick with natural fibers—merino, cotton, or a blend—because they regulate temperature better and don’t get funky by noon. On a sweaty subway ride, I want the fabric working with me, not trapping heat. If your base layer looks sad on its own, your entire outfit collapses once you step indoors.
Buck Mason Field-Spec Cotton Heavy Tee
Flint and Tinder Long Sleeve American Heavyweight Pocket T-Shirt
Carhartt Base Force Midweight Base Layer Classic Crew
Add In The Mid-layer
If the base layer is about comfort, the midlayer is about personality. This is where the outfit stars to do the visual heavy lifting: a brushed flannel or overshirt, a sweater or knit polo, or a lightweight fleece that doesn’t scream “hiking trip”. I want something warm but breathable, and ideally something I don’t mind wearing all day at my desk. This layer should be easy to remove, but still cool enough to wear if the office is blasting heat.
Arc'teryx Kyanite Jacket
Buck Mason California Cashmere Polo
Your Insulating Layer Should Trap Heat, Not Bulk
Most guys think warmth means thickness, but that’s not the case. You can stack and feel cozy without channeling Michelin Man energy. Instead, look for fabrics with a high warmth-to-weight ratio—like responsibly sourced down, merino wool, or synthetic insulation (think Primaloft or Coreloft)—that trap heat without adding bulk. I reach for a packable down puffer jacket or a slim wool cardigan under my coat. This layer should compress under your outerwear and disappear visually, while still doing its job when the temperature drops into the 20s.
lululemon Featherweight 900-Down-Fill Quilted Hooded Jacket
J. Crew Rugged Merino Wool-blend Cardigan Sweater
Cos Striped Merino Wool Cardigan
Cotopaxi Fuego Hooded Down Jacket
Outerwear
My outerwear has to look good, sure—but it also needs to earn its place in my rotation by doing the heavy lifting in bad weather. For commuting, I’m looking for wind- and water-resistance, enough room for layers underneath, and coverage that actually blocks cold air. Whether it’s a parka, a wool topcoat, or a technical shell, my outerwear has to work with the layers underneath. If I can’t zip it comfortably over a sweater and insulated layer, it’s not a winter coat.
The North Face Gordon Lyons Full Zip Jacket
Don’t Forget the “Micro Layers”
The smaller stuff matters more than you think. Accessories that can make or break a winter outfit, in terms of how well they regulate heat throughout the day. That’s where my winter non-negotiables came in: a beanie for my noggin, a real scarf (wool, leather or cashmere), gloves I can use my phone with, and socks that pull their weight. These pieces let me dial warmth up or down without changing my entire outfit. I loosen the scarf on the subway, tighten it for the walk home, and stay comfortable the whole time. Gloves are an easy on-and-off fix, while good socks are tall enough to layer over thermals without bunching or slipping.
Carhartt Knit Cuffed Beanie
Bombas Marl Calf Sock 4-Pack
Charles Tyrwhitt Leather Touch Screen Gloves
Paul Smith Fringed Striped Wool Scarf
Smartwool Liner Glove
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As the Style and Reviews Editor for Men's Health, Joseph covers all-things fashion and grooming. Previously, Cheatham was a commerce editor for Spy, and he has written for Travel + Leisure.
Christian is the Style and Reviews Director at Men's Health and Women’s Health, where he oversees shopping and style content for both brands. He started his magazine career as an accessories assistant at Vogue, and has since held editorial roles at Tatler Asia and The Manual. When he’s not online shopping, you can find him on long walks with his two corgis.
