Suddenly, Every Chic Dresser Is Swapping Their Trusted Winter Trends for These Surprising Comeback Styles

What do prim pill box hats, funnel-neck jackets and librarian-like pencil skirts have in common? They’re amongst the major trends making a comeback for winter 2025. Indeed, it appears that this season is taking sartorial cues from the looks of yore and embracing specific pieces and styling tricks that date back a few years. (Or even half a century, as is the case with the ‘60s silhouettes mentioned above.)

Though this proposition might make it seem that the winter that lies ahead will be rife with dated looks that really should be relegated to fashion’s boneyard for antiquated shapes, it actually couldn’t be further from the truth. As is the nature of the hyperaccelerated trend cycle, everything old is new again. So while you might receive an odd comment here or there from someone saying that they remember when your specific look was en vogue the first time, the collective mainstream will be none the wiser. In fact, some of these trends haven’t made an appearance in several decades, meaning that contemporary dressing techniques are even making these motifs feel fresh and cutting-edge.

Because what really is innovation for innovation's sake when there’s a rich history to look back on and draw inspiration from? That being said, what exactly are the key trends that are making a comeback for the winter of 2025? Generally speaking, cold weather months are typically more conservative than others, given how the frigid temperatures force us to bundle up under layers of clothes, so it’s fitting that the biggest returning trends pay homage to the ‘80s. (The era in which this ideology was most prominent.)

This is translating through the return of power dressing with boxy jackets that protrude at the shoulders and taper in the waist, pin straight trousers that sit high on the hips and jean-and-boots combinations that certainly feel like they’ve been ripped from the pages of a Jilly Cooper novel. Very Saint Laurent-esque.

Without any more time passing, scroll on to see and shop all the trends that are making a comeback this winter.

5 Fashion Trends Making a Comeback for Winter 2025

1. Wall Street Suiting

Style Notes:

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2. Cropped Trench Coats

Style Notes: Another hallmark of this decade to make a return is the cropped trench coat, especially when it takes the form of a bomber jacket like the one pictured. While not a classic aviator fit, the billowing and languid structure of this comeback trend softens the formal and austere essence that’s innate to the garment. Past iterations might’ve been sported with something like a club stripe tie, however, these days it’s being worn with everything from slouchy bottoms to long, lace-trim tops.

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3. Slouchy Boots

Style Notes: While I won’t exhaust the metaphor too much, it’s clear to see that this comeback trend also harks back to the ‘80s. This time, though, the look is considerably more Cotswolds-approved than anything else we’ve seen. Particularly when tucked into jeans and styled with a preppy fashion pinstripe blazer like this, slouchy boots shed all their connotations with the early 2000s and parallel something you would’ve spotted on the sidelines of royal polo matches in Windsor. Incredibly Rivals coded, in the best way possible.

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4. Collarless Blazers

Style Notes: Finally, a trend for those who are getting slightly fatigued by all these late 20th Century throwbacks! While the first appearance of a collarless jacket can be rightfully attributed to Chanel when the French maison debuted them in 1925, I’d contend that the style is more popular than ever, exactly 100 years later. Intentionally refined and endlessly ladylike, this trend pairs well with more body-conscious garments, like the leg-skimming stirrup leggings and glove-fit, rounded pumps styled above.

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5. Double Shirting

Style Notes: Another style that’s supplanting itself back into fashion’s lexicon is the layered t-shirt trend. Sure, this is something you would’ve seen Seth Cohen from The O.C. wear in the early 2000s, but irrespective of all its ties to surfers and skate rats, there are so many stylish dressers who are making a case for its comeback. From The Row to Wales Bonner’s latest collaboration with streetwear brand Stüssy, consider this a look that’s rightfully been given a high-fashion makeover.

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