Winter, we’ve been waiting for you. The air is crisp, the layers are cozy and your wardrobe? It’s about to get a lot more interesting.
This season, our Stylists are forecasting a mix of the unexpected: vintage-inspired outfits, bold romance, easy resort vibes and voluminous silhouettes—all designed to bring a little extra fun to your winter style.
At Stitch Fix, our trend forecasts aren’t just guesses—they’re grounded in deep industry insight and data from our in-house experts (and clients like you). Think of it as your insider look at what’s next in fashion, backed by pros who live and breathe style.
Not sure where to start? That’s where our Stylists come in. They help take the trends off the runway (and out of the group chat) and turn them into looks you’ll actually want to wear. Best of all, our Stylists help you find pieces that fit, flatter and fuel your confidence. We do the shopping for you, saving you time while making your wardrobe—and your day—feel a whole lot easier. With a mix of effortless classics, fresh updates (plus a few fun surprises), we can help you work these pieces into your closet in a way that feels totally you.
Ready for your first look at what’s next in winter fashion trends? Consider this your personal sneak peek at the styles showing up in your next Fix.
1. Retro Supreme: Midcentury Style, Modern Revival
Everything old really is new again—and we’re not mad about it. Inspired by the buzz around the Timothée Chalamet film Marty Supreme, this trend channels 1950s flair with crisp tailoring, playful prints and a dash of nostalgia. Our Stylists are calling it “smart casual with vintage soul,” and we couldn’t agree more.
“Midcentury-inspired pieces have this magnetic blend of nostalgia and modern polish,” explains Stylist Caro. “The clean lines and playful prints remind us of a classic era, but when styled with contemporary silhouettes, they feel fresh and relevant. It’s that perfect mix of familiar and new that makes people fall in love with them all over again.”
To bring 1950s style outfits into winter, Stylist Mathew offers his favorite take: “Start with a classic button-down as a base layer and add a tea-length skirt. Finish with a boxy jacket as your go-to outer layer.”
Want a little more whimsy? Polka dots are also back, with client requests for polka dot styles climbing 175% since last year. Try a polka dot dress with a studded bag for a playful, pattern-on-pattern twist. Not feeling that bold? “I love it in a fun patterned skirt, then warming it up with a cozy sweater and tall boots,” says Stylist Kate. Easy, chic and just the right touch of retro.
“Midcentury-inspired pieces have this magnetic blend of nostalgia and modern polish. The clean lines and playful prints remind us of a classic era, but when styled with contemporary silhouettes, they feel fresh and relevant.”
-Stylist Caro
2. Dark Cupid: In the Mood(y) for Romance
Move over, bubblegum pink—romance is getting a bold makeover. This trend fuses deep, moody tones with luxe textures like velvet, lace and leather for an aesthetic that’s equal parts drama and dreaminess. Think of it as Valentine’s Day…after dark.
“There’s something really effortless about pairing romantic, silky fabrics with structured layers,” explains Stylist Caro. “In fact, client requests for romantic styles have increased nearly seven times since last year, which shows how much people are embracing that softer, moodier side of winter dressing. A lace cami under a tailored blazer or a slip dress with chunky boots creates this balance between softness and edge. It’s equal parts dreamy and cool—a combo that never really goes out of style.”
Need date-night looks for winter? Stylist Kate suggests leaning into rich color and texture. “A classic black dress and a velvet blazer will bring those romantic vibes and keep you warm in the cooler weather.”
Bringing that moody energy into daylight? Easy. Stylist Jackie’s pick: a fitted puff-sleeve top with a flowy maxi skirt. “It’s chic enough for work and romantic enough for dinner after.”
If you’re still unsure how some of these pieces 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!
“There’s something really effortless about pairing romantic, silky fabrics with structured layers.”
-Stylist Caro
3. Anchors Away: Nautical Styles Set Sail
Cruise culture is getting a refresh and wardrobes are following suit. Our Stylists have seen a sharp rise in clients asking for cruise outfit ideas and resort wear that actually fits real life (not just the pool deck), with client requests for “breezy” styles up nearly 700% since last year. Enter Anchors Away, a trend that channels carefree, resort-ready energy with drawstring trousers, cinched-waist dresses, crisp cottons and nautical stripes that feel timeless, not touristy.
“Consider it permission to daydream about warmer places—and dress like you’re already there,” says Stylist Kate. Start with breezy white linen or a soft striped dress, then add your own spin: a woven bag, loafers, maybe a touch of gold jewelry.
If you’re packing for a getaway, this is resort wear for women at its breeziest. If you’re staying put, Stylist Erin’s got you: “Layer a cozy crochet sweater over a knit linen-blend top. Style with wide-leg jeans and suede boots for that coastal winter look.” Effortless, elevated and totally wearable, no passport required.
“Consider it permission to daydream about warmer places—and dress like you’re already there.”
-Stylist Kate
4. Volume Up: Wide-leg Jeans and Pants for Women Take Center Stage
Big pants, bigger energy. This winter, silhouettes are taking up space—and we’re loving every oversized inch. From wide-leg jeans to billowy workout pants and genie-inspired bottoms, this trend is all about volume with intention. Requests for relaxed pants have skyrocketed—up more than 16x since last year—and oversized styles are up 80% too, proving that comfort and confidence are officially the new power duo.
The trick is all about balance—pair your voluminous pieces with something fitted or structured to keep your shape defined. Think sleek turtlenecks tucked into flowy trousers or a cropped puffer paired with barrel-leg jeans.
Even athleisure styles are seeing a shift into oversized silhouettes. Stylist Jackie says she’s seeing clients gravitate toward looser fits that move with them: “Swap your leggings for wide-leg pants to add maximum comfort.” The result? A laid-back, confident vibe that feels just as good as it looks.
Need more help styling an oversized outfit? 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!
“Swap your leggings for wide-leg pants to add maximum comfort.”
-Stylist Jackie
Get styled by Stitch Fix for 2026
Excited to see how these 2026 winter fashion trends could work in your own closet? Your Stitch Fix Stylist is ready to make it happen. 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 keep 5+ pieces and get 20% off your entire order. Shipping and returns are always free—no subscription required. It’s as easy as 1, 2, 3.
