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If you tackled No Jeans January, SG’s 31-day wardrobe challenge, you already know this plot twist.
Once you take denim off the table for your everyday casual winter outfits? Your outfits get a lot more interesting.
What takes some guys by surprise? How comfortable these denim-free looks can be.
Tailored sweats tagged in for everyday wear. Corduroy pulling its cozy weight. Chinos feeling just like your favorite pair of denim.
Somewhere between #NJJ weeks two and three, it clicks: casual winter style doesn’t have to mean sloppy.
So, consider this roundup of jeans-free casual winter outfits a nudge towards keeping up that creative energy next month…and beyond!
These looks are perfect for cold mornings, long afternoons, and those “I’ll leave the house… maybe” days.
Turns out when you mix soft textures with warm layers, you get low-effort looks with maximum style impact. Perfect for if you do actually leave home…or if you stay curled up on the couch with a good book.
February may be short, but it’s still winter—so you might as well make your wardrobe work for you with comfortably cozy, stylish ‘fits.
Keep scrolling for 31 days of winter style inspiration:
1. A quarter zip and corduroys
Shop this look: quarter-zip sweater | pants | sneakers | cotton tee
The “quarter zips are cool again” train is chugging along in 2026. Wear yours with a pair of white sneakers and comfy corduroy pants.
2. Tailored joggers and a hoodie
Shop this look: joggers | hoodie | sneakers
Top the hoodie with whatever heavy jacket is necessary for February.
3. Rollneck sweater and 5-pocket pants
Shop this look: sweater | pants | sneakers
Rollneck sweaters are back, baby. Wear yours with black 5-pocket pants and a soccer-adjacent sneaker.
Layer a sport shirt underneath if the spirit moves you.
4. OCBD and jewel-toned trousers
Shop this look: oxford shirt | pants | sneakers
This outfit would work perfectly for a business casual office. I’m slightly obsessed with these sneakers from our pals at Greats (who helped us put #NJJ on this year) and hope to see more guys wearing the dadcore style.
5. Rugby shirt and slip-on sneakers
Shop this look: rugby shirt | pants | sneakers
Finishing an outfit with a multi-color rugby shirt is like topping a pizza with pepperoni. It’s always a good idea.
6. Fleece over a tee
Shop this look: jacket | joggers | cotton tee | sneakers
As if I need to convince you to slip into sweats this winter. Joggers are perfectly acceptable to leave the house wearing, so long as they’re tailored like this Taylor Stitch pair.
7. Black pants with a crewneck sweatshirt
Shop this look: knit crew | trousers | sneakers
One of my favorite men’s looks from No Jeans January, I love how this grey and black outfit can take you from the workday to a date night.
8. Plaid overshirt and fatigue pants
Shop this look: overshirt | pants | sneakers
This outfit feels very Gabi-coded to me. Cool, comfortable, ready to elicit compliments from your most fashionable friends.
Wear the overshirt open over an off-white tee, or buttoned up for extra-cozy vibes.
9. Loafers and drawstring pants
Shop this look: sweater | trousers | loafers
Just because the lakes are frozen over doesn’t mean you can’t look like you’re ready to hop on a boat.
Add a pair of white dress socks for a nerdy-cool vibe that also keeps your ankles warm.
10. Sweater vest and sneakers
Shop this look: sweater vest | pants | oxford | sneakers
The sweater vest’s reign continues into 2026. Wear yours over an OCBD or tee, depending on the temperature.
11. Pleated pants and a rugby shirt
Shop this look: sweater | trousers | sneakers
Topping a casual outfit off with a long-sleeve rugby shirt makes any outfit 10x cooler.
12. Statement pants and a hoodie
Shop this look: overshirt | hoodie | trousers | sneakers
Let your pants do the talking with a statement pair in bold black and white. Keep the rest of the look simple with casual sneakers and a chambray shirt layered under a hoodie.
13. Earth tones outfit
Shop this look: sweater | pants | sneakers
Sometimes it’s a crazy pants day, and sometimes it’s a henley and chinos day. Choose your fighter, as they say.
14. Camo pants and a cozy vest
Shop this look: vest | overshirt | pants | sneakers
Here at SG HQ, we’re very pro-mixing patterns. In this case, camo workwear pants with a Hickory stripe top.
15. Colorblock hoodie and corduroy pants
Shop this look: hoodie | trousers | belt | sneakers
Even the most color-averse guy can get down with an outfit awash in hues of blue.
16. Sweater polo with chinos
Shop this look: knit shirt | pants | sneakers
A sweater polo in a bright color pops for a drinks date, or a night out with friends.
17. Workwear pants and a shearling jacket
Shop this look: jacket | cotton tee | pants | sneakers
You can get away with a t-shirt if the coat you wear over it is as warm and cozy as this bad boy.
Want more warmth? Add a cardigan in between the layers.
18. Stripes with joggers
Shop this look: rugby shirt | joggers | hat | sneakers
Joggers in chocolate brown look surprisingly sophisticated. Wear them with a striped shirt and bright white sneakers.
19. Shorts and a sweater polo
Shop this look: button-up sweater | shorts | pocket tee | loafers
Working from home? Slip into drawstring shorts and drivers with a sweater polo topping the whole thing off.
20. Spring colors and white sneakers
Shop this look: button down shirt | pants | sneakers
This outfit gives the impression that spring might actually be around the corner. Now let’s just see if the groundhog sees his shadow or not.
21. Light layers with penny loafers
Shop this look: sweater | button-down shirt | chinos | loafers
Another outfit that suggests temperatures could be rising in the foreseeable future feels like a beacon of hope in the trenches of February.
22. Corduroy pants and suede sneakers
Shop this look: crewneck sweater | pants | sneakers
No matter the season, a pair of drawstring pants can take a starring turn in your casual outfits. In winter, turn to corduroy to ratchet up the warmth factor. A cozy crewneck helps, too.
23. dark overshirt and drawstring pants
Shop this look: overshirt | pants | sneakers
Matching your top layer to your footwear is an easy way to create a cohesive look with your casual outfits. Don’t worry; it won’t look too “matchy-matchy.”
24. zippered cardigan over a thermal shirt
Shop this look: zip-up cardigan | sneakers | thermal shirt | joggers
This cashmere sweater looks just as good with joggers and your favorite sneakers on the weekend as it would with dress pants and laced boots for work.
25. sporty hoodie with shorts
Shop this look: hoodie | shorts | sneakers | socks
For the guy who thinks there’s no temperature low enough to stop wearing shorts.
26. suede loafers with a sweater polo
Shop this look: striped sweater | trousers | loafers
This simple and sophisticated outfit would look great at a business casual office or on a winter date with your wife or girlfriend.
Swap the loafers for something more substantial if there’s snow on the ground.
27. a bold overshirt with black sneakers
Shop this look: patterned overshirt | pants | sneakers
Keep the rest of your look simple when wearing a patterned overshirt that’s ready to be the star of the show.
28. a suit styled casually
Shop this look: double-breasted blazer | turtleneck | suit pants | sneakers
Yes, a suit can be casual. Worn with sneakers and a sweater instead of dress shoes and a button-up shirt, this look reads special date night rather than office-reaady.
29. short sleeves and suede sneakers
Shop this look: short-sleeve shirt | pants | sneakers
Because not every guy lives somewhere that long sleeves are essential in the winter months!
30. fatigue pants with a striped long-sleeve tee
Shop this look: Breton stripe shirt | utility pants | sneakers
A Breton stripe shirt is a classic casual outfit staple, no matter the season. Pair it with of-the-moment pants and you’ve got a crisp, cool look for cold weather.
31. a bright sweater and white sneakers
Shop this look: Fair Isle sweater | pants | sneakers
Don’t shy away from a seasonal sweater after the holidays, especially when it’s in a non-traditional color like bright blue and green.