When temps drop, your outfit should work just as hard as you do. Winter outfits for men should be warm, functional and easy to put together—and that’s exactly where Stitch Fix Stylists come in. They’ve done the thinking for you, building ready-to-wear looks for your next Fix that cover everything from chillier commutes to cozy nights in.
This is your ultimate guide to men’s winter outfits—straightforward, comfortable and easy. No overthinking required.
1. Conquer the Cold: Men’s Everyday Style
When the chill hits, layering is your best friend. A great jacket—think quilted, barn or shirt jacket (aka “shacket”)—adds instant polish while keeping warmth locked in. Pair it with a textured sweater or fleece for extra insulation and dark jeans that go with everything.
Complete your look with weatherproof boots and a cool beanie, and you’ve got a go-to winter outfit that’s both rugged and refined. Stylist Carolina adds, “Comfy, practical and stylish—these essentials keep you warm and ready for anything the season throws your way.”
Easy outfit formula: Quilted or barn jacket + comfortable sweater or fleece + dark denim + lug-sole boots + beanie
Wondering what a new-to-you trend or style might look like on? Try our newest app exclusive, Vision. It utilizes AI to generate personalized images of you styled in the latest looks and trends. You can then browse and shop these styles instantly!
“Comfy, practical and stylish—these essentials keep you warm and ready for anything the season throws your way.”
-Carolina, Stylist
2. Work Smarter: Men’s Winter Office Outfits
Winter workwear doesn’t have to mean sacrificing style for warmth. Our Stylists suggest swapping your button-up for a sweater with a graphic pattern or a sweater polo (aka “swolo”) to bring personality to your 9-to-5 rotation. Pair it with clean, structured trousers and smart leather or sueded boots to pull it all together. Stylist Kate adds, “An important layering tip is to wear different textures to add interest to your whole look.”
This works because it’s still professional but never stiff—warm layers meet office polish, making it one of the most reliable men’s winter workwear outfits out there.
Easy outfit formula: Cool sweater style + tailored trousers + sharp boots
Need more styling advice or help with date-night dressing? You can now chat directly with one of our expert Stylists! Head to our app to access Stylist Connect and start your conversation with a Stylist. Ask all your outfitting questions or even collaborate on your next Fix together!
“An important layering tip is to wear different textures to add interest to your whole look.”
-Kate, Stylist
3. Work Out or Chill Out: Men’s Winter Activewear
For days spent moving—or not moving much at all—comfort takes priority. But with the right mix of men’s winter loungewear and gym clothes, you can look put-together while staying comfy.
Stylist Kate says, “For those chill days at home this winter, try a great pair of joggers with a performance hoodie.” She adds, “Then if an errand pops up, throw on some sneakers and you are ready to go!”
We suggest wearing a hoodie or windbreaker in a fun, bright color. Stylist Carolina adds, “A fresh pop of color like red or green can liven up your whole look.” You’ll love this look because it keeps you warm without overheating, whether you’re headed to the gym or just grabbing coffee.
Easy outfit formula: Lightweight windbreaker + fun hoodie + fleece joggers + active sneakers
“A fresh pop of color like red or green can liven up your whole look.”
-Carolina, Stylist
4. Look Sharp: Men’s Winter Date Night Outfits
When the night calls for a little extra effort, winter date night outfits for men are all about subtle polish. Stylist Caro says, “Layer a crisp sweater under a jacket, pair with dark jeans or trousers, and finish with your favorite boots.” A refined shacket or wool jacket layered over a textured knit creates instant sophistication. Stylist Mathew adds, “Mix and match neutral tones like black, navy, khaki and gray for easy winter outfitting.”
Darker denim is a casual-yet-dressed-up option thanks to its wash. Or when in doubt, you can always go for classic trousers. Finish with sleek leather boots and you’re ready to go. This combo is confident but not too much—perfect for dinner out, a movie or a night downtown.
Easy outfit formula: Sleek jacket + dark denim or slim trousers + elevated shoes
“Mix and match neutral tones like black, navy, khaki and gray for easy winter outfitting.”
-Mathew, Stylist
Build Your Winter Lineup with Stitch Fix
No mall trips. No guesswork. Just easy, functional winter clothes for men. Partner with your very own Stylist who really gets to know you and your unique style. Take your style quiz, order a Fix and let your Stylist do the work for you. They’ll choose just-for-you pieces to save you time (and a trip to the mall). Keep what works, and return the rest—or get special discounts when you keep 5+ pieces. Shipping and returns are always free—no subscription required. It’s as easy as 1, 2, 3.
