I think we can all agree that what’s “cool” is totally subjective. If great design is a given, other common denominators include authenticity, not seeming try-hard and a sense of originality. But whether it’s Rihanna, Charli XCX or the influencers’ looks you regularly screenshot, I’d wager that they’ve worn at least one of the following recently as the temperature has dropped: a leather jacket, baggy jeans or statement sneakers. Am I right?
Whilst social media has definitely accelerated the rate at which “cool” fashion trends are discovered and discarded—and kudos to the agenda-setters and earlier adopters—one person’s “cool” can still be someone else’s “cringe”. We’re gravitating towards similar things, but what makes your outfit feel “coolest” to you is how successfully you project your one-of-a-kind personality when styling your winter wardrobe.
As a graduate in fashion history and theory, I always want to dig a little deeper, and my research uncovered a recently published Journal of Experimental Psychology paper by Todd Pezzuti, Caleb Warren and Jinjie Chen, which pinpointed six attributes that “cool” people are perceived to possess. I realised that the “cool” fashion trends I’ve seen bubbling up for 2026 are aligned to this theory: extroverted, open, hedonistic, adventurous, autonomous and powerful.
From ‘80s flashbacks and pirate aesthetics to brooches and the Balenciaga City Bag and Nike Shox to furry moon boots (yes, really), keep scrolling to choose which of the coolest 2026 fashion trends speak to you, then shop them with the confidence that you can pull anything off.
7 Cool Fashion Trends That Will Be Everywhere in 2026
1. ’80s Groove
Style Notes: Don’t call it a comeback; it’s a full-blown ’80s-maximalism takeover at this point, according to Pinterest and other sources. If you’ve admired recent Saint Laurent runway shows, been drawn to a funnel-neck top or jacket, supersized your suit or snapped up some pointy slingback heels over the last few months, you’re already ahead. Depending on your commitment to this 2026 shift, you could wear these cool pieces all at once, as pictured, or deploy them separately to power up your fail-safe staples.
Shop the Trend:
Prada
Oversized Pilot Sunglasses
Slip these on whilst strutting through the winter sunshine.
COS
Funnel-Neck Jersey Top
Tuck this into skirts, jeans and tailored trousers for work and cocktails alike.
Chunky face-framing hoops are a no-brainer, and these also come in silver.
Toteme
Paneled Leather Skirt Black
You can wear this leather skirt anywhere, dressed up or down.
ARKET
Croco-Embossed Clutch
Go hands-free with a clutch bag so the outfit flow isn’t broken.
Saint Laurent
Apolline Slingback Pumps in Patent Leather
These are the exact black Saint Laurent slingback heels pictured.
2. Balenciaga City Bag
Style notes: During the noughties, supermodel Kate Moss was the ultimate British It girl, and she often had the Balenciaga City Bag dangling from the crook of her arm. It was the brainchild of then-creative director Nicolas Ghesquière, and launched in 2001 as the Motorcycle City Bag to supposedly reflect the edgy moto-jacket-inspired details. Of the viral It bags currently in circulation, City Bags of any size or age still have the same captivating aura. It’s the colour choice and addition of decorative bag charms that make certain iterations stand out.
Shop the Trend:
Balenciaga
Pre-Loved Le City Bag
Fewer people own this colour, and the shade is perfect for spring.
Balenciaga
Medium Le City Bag
This should be big enough to carry your laptop and lunch when heading to work.
Balenciaga
Small Le City Bag
Choose camel to neutralise brights and anchor all-black looks.
Balenciaga
Pre-Loved Le City Bag
This bag only gets better with wear and age, and this one is a case in point.
Balenciaga
Medium Le City Bag
Utilise the longer, removable strap to carry this bag on your shoulder or crossbody.
Balenciaga
Pre-Loved Le City Bag
The biggest styles can replace your trusty weekender bag.
3. Shirt and Tie
Style Notes: Once you get over the school uniform and “client-facing-finance-bro” connotations, it’s easy to conclude that wearing a shirt and tie together is a novel refresher for smart outfits. A button-down shirt is a capsule-wardrobe mainstay, which already makes this trend easier to tap into, and the size and length of your tie can be customised when you knot it. Keeping the colours tonal and complementary reads more chic than preppy, unlike matte collegiate stripes that admittedly animate plain tailoring.
Shop the Trend:
M&S
Cotton Blend Shirt & Tie
Sticking with different shades of blue makes this pairing seasonless.
Tommy Hilfiger
Pure Silk Jacquard Tie
A tie like this can be shared amongst friends and partners.
Jigsaw
Cotton Poplin Shirt
Your search for a classic white shirt ends here.
Ralph Lauren
Vintage-Inspired Striped Silk Tie
This tie may transport you back to school, but in this case, that isn’t a bad thing.
M&S
Cotton Collared Shirt
Proof that a black shirt is an good option for everyone, not just bouncers.
So sleek and perfect for after dark.
4. Nike Shox
Style Notes: I got my first Nike Shox in 2003 and my most recent pair of Nike x Martine Rose Shox MR4 mules (white, grey and red) last month. They are technically the most comfortable, high-performing heels I own, which is why I craft sportier night-out outfits around them. Those impact-absorbing columns at the back give you a welcome lift as you bounce along. There are now enough colourways and design tweaks to challenge the ubiquity of other sneakers.
Shop the Trend:
The pop of red is another big 2026 trend.
Neon green goes with neutrals and other bright shades.
Okay, ombré. This is a gorgeous colour combination.
Additional columns become a distinctive design detail.
A graphic take on monochrome trainers.
Iridescent and oil-slick details level up this all-black edition.
5. Piratecore
Style Notes: Not just Napoleon jackets or ruffled blouses, cue the bandana, which is associated with pirates by popular consensus, even though the historical accuracy is questionable. Certain friends and stylish women on my radar wear these square or triangular paisley headscarves religiously, not just to cleverly hide hair in need of a wash, but also as a fun way to insert contrasting colour into plainer outfits. Adding chunky hoops can lean obvious, but it’s still cool and slightly boho.
Shop the Trend:
Damson Madder
Multi Use Bandana
This one is big enough to be tied around your head, neck or waist.
These everyday hoops transcend trends.
Red is the classic bandana colour.
Free People
Triangle Bandana
Ivory and burgundy is softer.
What a great shade of olive to team with denim.
A less-is-more addition to your earrings collection.
6. Brooches
Style Notes: Jewellery is only getting chunkier, bangle stacks are rising up the arm and a great way to jazz up your outerwear is to affix an eye-catching brooch to your chest or sleeve. Grace Wales Bonner’s mixed-media talismans and inherited heirloom trinkets immediately come to mind to nail the vibe, and I’d recommend going for gold when picking an original shape or sentimental motif. Animals, gemstones, ornate swirls, evil eyes, medallions—anything goes, and you can always pin on more than one at once.
Shop the Trend:
Wales Bonner
Compass Brooch
Let this cross brooch shine against black or white.
Anthropologie
Candy Brooch
This floral is groundbreaking for spring.
Ellie Vail Jewelry
Joss Hammered Circle Brooch
Thread through a chain, and this brooch becomes a necklace pendant.
This sculptural bow is minimal but impactful.
Completedworks
Crumple Tie Pin
Made from recycled gold vermeil, this creased brooch is impressive.
7. Furry Boots
Style Notes: They’re essentially cosy moon boots covered in faux fur. Did anyone else see them and recall S Club 7’s festive hit “Never Had A Dream Come True”? Or how Beyoncé styled hers with Western-inspired attire during her Cowboy Carter era? The main takeaway, beyond how Y2K-coded and seemingly impractical these boots are in wet weather, snow and on pavements, is that they, surprisingly, aren’t limited by season, temperature or location. They may not be for the fainthearted, but there’s no denying they’re a “thing”.
Shop the Trend:
These knee-high faux-fur boots are an official collaboration with Moon Boot.
Bored of smooth suede? Stroke these instead.
Free People
Wild Thing Mid Boots
They work for après-ski and post-pilates alike.
UGG
Classic Short Fluff Momma Boot
Do you prefer these in black or pink?
Steve Madden
Beastie Boot
Consider these slippers that you can wear outside.
MOON BOOT
Icon Snow Boots
These were made to be worn in the snow.
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