As the days get colder, a fresh wave of winter style is emerging. This season’s (style) forecast? Vintage-inspired tailoring, bold shapes and rich textures that bring warmth and confidence to every look.

Below, we outline the latest trends with tips from our Stylists on how to bring them to life.

Retro Supreme: Midcentury Style, Modern Revival
Retro Supreme channels midcentury silhouettes and timeless tailoring. Inspired by the buzz around Marty Supreme, clients are gravitating toward crisp cuts and playful prints. Requests for “retro” styles have increased over 30% and “polka dot” requests have surged 175%, while sales of structured jackets are up by more than 30%, signaling a return to classic, confidently tailored dressing. With celebrities like Ariana Grande embracing polka dot gowns and Sabrina Carpenter recently sporting tailored vests and iconic suiting, this vintage-inspired trend is just as suitable for the red carpet as it is for everyday wear.

How to wear it, according to Stitch Fix Stylist Melissa Wright: For Women, pair a tailored jacket with high-waisted trousers for a look that feels both classic and current, adding texture with a polka dot blouse. For Men, try a blazer over slim or straight leg trousers with a patterned shirt or knit for a playful touch. Finish with loafers to keep the look polished yet modern.

Dark Cupid: Romantic Edge with a Moody Twist
Romance takes an edgier turn this winter, with Dark Cupid reimagining classic Valentine’s hues with rich textures, dark florals and flowing silhouettes that feel dramatic yet wearable. Fueled by the buzz around Wuthering Heights (hello, Margot Robbie!), Women’s clients are leaning into this moody, feminine look. Requests for “romantic” styles have increased nearly 7x, while “puff sleeve” mentions are up over 90%. Velvet pieces are also on the rise, with sales up 50%, proving that elegance with attitude is having a moment.

Stitch Fix Stylist Julie Ward shares her go-to combo for achieving this trend: Our Women’s clients can try pairing a lace-trim blouse with dark denim and leather boots for an easy nod to the trend. For a more dramatic look, opt for a velvet dress or flowy skirt in deep plum or burgundy. Finish the look with metallic jewelry or a deep cherry lip to make winter romance feel modern.

Anchors Away: Nautical Style Sets Sail
For those gearing up for a warm weather getaway or living in a year-round warm climate, take inspiration from a trend we’re calling Anchors Away. With the rise of micro-cruises and coastal getaways, this resortwear aesthetic takes nautical style in a more effortless direction. Client requests for “breezy” styles are up nearly 700% and interest in “stripes” has climbed more than 60%. Sales of Women’s linen pieces are also up nearly 40%, proving coastal-inspired style is setting sail for our vacation wardrobes.

Stitch Fix Stylist Ramon Sorstokke’s favorite way to style it: For Women embarking on a cruise or jetting off to a tropical vacation this winter, style wide-leg or drawstring pants with a crisp tank or striped knit to balance ease with polish. Add lightweight layers like a relaxed cardigan or linen blazer, finishing with boat shoes for a look that channels coastal sophistication. For Men, pair relaxed linen trousers with a fitted polo or short-sleeve button-down, finishing with clean white sneakers.

Volume Up: Wide-Leg Style Takes Center Stage
Silhouettes are expanding this winter, and comfort is coming with them. Volume Up celebrates the rise of wide-leg and flared pants that blend style with ease. Clients are all in with requests for “relaxed” styles having increased by more than 16x, while requests for “flowy” bottoms are up over 30%. Sales of wide-leg and flared athleisure pants have climbed by more than 125% as well.

Stitch Fix Stylist Kelline Gorecki offers this outfit idea: To help Women’s clients nail the look and ensure balanced proportions, we’ve developed a simple styling approach: The 60/40 Rule. Roughly 60% of your outfit’s visual “weight” should come from your wide-leg pant, balanced by 40% up top through fitted, tucked, or cropped pieces. The result is a shape that feels modern, flattering and effortlessly put-together.

Methodology: Unless otherwise stated, all client request data compares Q1 FY25 vs Q1 FY26 to date, as of October 16, 2025. Unless otherwise stated, all sales data compares January-October 2024 vs January-October 2025.