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How to Dress Cozy While Staying Stylish

How to Dress Cozy
While Staying Stylish

By Megan Gustashaw

As the weather cools and the days get shorter, it’s tempting to get dressed for comfort over style. The good news about the state of menswear in 2018? You don’t actually have to choose. Thanks to the rise of athleisure, athletic wear, streetwear, and every other trend involving drawstring pants, off-duty, warmth-enhancing clothes are sharper than ever. Case in point: our Sherpa fleece hoodie, which feels like a cozy couch blanket but looks like a rich-guy sweater. Combine this winter workhorse with our leather boots and your bottoms of choice and you’re the best-dressed guy cruising into cozy town. For proof, check out these ways to wear the layer, each one perfect for one of the season’s weekend activities.


For those cold weekend days and nights when you’re watching the game, catching up with an old friend over a beer, or just reading at your local coffee shop alone, our gray Sherpa fleece if your best companion. It’s just like your typical weekend hoodie, but made a little bit cozier and more luxe thanks to its plush fabrication. Plus, this hoodie goes with everything—black, brown, gray—so you don’t need to stress the details. Just grab your favorite jeans and your lace-up boots and you’re good to go.



Whether you’re making the trek home or already chilling on mom and dad’s couch, spending time with family at the holidays requires a slightly more festive wardrobe that’s also primed for movie-watching. Our red check Sherpa fleece is just the thing. It looks sharp and alert even though it feels like PJs and looks excellent with your favorite gray joggers and lace-up black boots (which you’ll immediately kick off).





Driving to dinner on a farm, winery, or in some cozy ski village? Fun activity, tricky style territory. Here’s an idea that’s stylish, warm, and polished enough for Pinot Noir: our snowflake fleece, black flannel trousers, and black Chelsea boots worn with your heaviest rag socks. Your fireplace ‘grams are going to look extra good when you’re wearing this look—and you’ll sink right into that cozy leather chair too.