
Dressing for transitional weather can always be tricky, but especially when you live in the UK. One minute, you’re contending with balmy temperatures, the next, there’s an icy chill in the air or a sudden downpour. Whilst we have had our fill of layering over the last few years (be it dresses over jeans, polo over polo, or doubled-up T-shirts), in 2026, there’s one piece which feels fresher and cooler, layered or not: the plaid shirt, a piece everyone is styling in 2026.
Now more recently a signifier of prep and polish (Ralph Lauren, anyone?), the plaid shirt’s roots are a little more humble. Made popular in the 70s and ‘80s as women increasingly adopted men’s practical workwear, by the time the ‘90s rolled around (and plaid shirts met visionaries like Vivienne Westwood and Kurt Cobain, Lorelai Gilmore, Dolly Parton and, of course, the cast of Friends), their transition into a slightly rebellious, grunge Americana was well and truly cemented.
(Image credit: Shutterstock, Getty)
Whether you call it flannel, plaid, or a simple checked shirt, fast-forward 30-odd years and the laidback button-down has become the hottest layer to wear. It’s latest reinvention at the hands of Matthieu Blazy era Bottega Veneta (the Spring/ Summer 2023 show, to be exact), transformed the check from dull to one of the most luxurious pieces going. And who better to bring about a shift than supermodel Kate Moss herself? Sauntering down the runway in croc-print ballet flats, low-waisted washed jeans, a white tank top and a plaid button-down, its simple proportions and eye-catching hues instantly made it a favourite. I mean, Jacob Elordi adored it so much he wore the look in the last season of Euphoria.
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After The Row’s viral red checkered iteration garnered a cult following when it strutted down the runway for S/S ‘2025, a rotation of vibrant lumberjack-inspired silhouettes lined the high street, and it couldn’t be clearer that plaid shirts are back on the fashion agenda. But once you’ve found the one, the next big question becomes: how do you style it?
For Amy Shaw Creative Director of London based brand Fuchsia Shaw, the appeal of the throw-on-and-go layer always been there. “I first came out with shirts in 2020 and when I relaunched in 2024, I always got questions about whether we’d bring them back. They are quite a timeless piece that people never tire of!” And when it comes to styling, Shaw has a refreshingly unfussy approach. “I’m always tying one around my waist over a really simple outfit, usually a long-sleeve basic with corduroy trousers, because it adds something without feeling overdone and it’s there if I get cold.”
Keeping things boxy and oversized, and balancing the slightly masculine shape with dainty accessories, her styling trick feels refreshingly current right now as fashion continues to dip into bygone eras, a sentiment Shaw shares: “I think plaid is having such a moment because there’s a real nostalgia to it, but styled in a more feminine way it feels really current. For me it’s the ultimate low-effort, still stylish piece”.
After scrolling through my social media feed, I’ve found a number of stylish dressers having fun with the flannel. Whether it’s worn backwards with the collar facing up, tucked into shapely barrel-leg jeans, or layered with a printed skirt and boots, this year, the fashion set is plaid shirted to the max. Scroll down to see my seven favourite looks and of course, you can shop the full outfit below.
7 Ways to Wear a Plaid Shirt in 2026
1. The Minimalist
Style Notes: Arguably the easiest way to wear a flannel shirt this season (much to the point of Amy Shaw) is tied around the waist. Breaking up a minimal look with its vivid colour and boxy, utilitarian charm, it functions as a handy, additional layer when the weather inevitably drops. If in doubt, look to Annabel Rosendahl [pictured above] for inspiration. From her washed-black stovepipe jeans to loose cotton top and The Row’s Tori bag to finish, this is off-duty styling at its very best.
Shop the Look:
With Nothing Underneath
The Classic
Whilst Annabel’s viral The Row shirt is still sold out everywhere, theres no need to fret as With Nothing Underneath’s uber luxe offering comes as the next best thing.
M&S
Pure Cotton Relaxed Top
As you can see, shirts ties around the waist is the coolest way to style them this season.
Agolde
90’s Pinch Waist Crop High-rise Straight-leg Jeans
A best-selling style in a perfectly distressed wash.
Crafted from functional canvas, flat leather straps, and outer front patch pocket, The Row’s minimal Tori bag is well placed to become your everyday go-to style.
Archies Footwear
Arch Support Flip Flops
On a cooler day swap Annabel’s flip-flops with a functional pair of loafers or trainers.
2. The London It Girl
Style Notes: Call me biased but, I’ve always maintained that Londoners’ sense of style is one that few can rival. And naturally, this extends to styling a plaid shirt. Take Alice Satterthwaite’s look [pictured above], as the perfect example. Shrugging on a blue-and-black iteration around her shoulders, she pairs fashion-forward shapes like low-rise cargos with classic pieces like a high-neck top to create an outfit that feels as carefree as it does stylish. If you’re looking to recreate it on a cooler day, swap out her flip-flops for a gathered loafer and finish with a warm chocolate brown tote. It’s an easy styling switch that keeps the laid-back energy going.
Shop the Look:
Reformation
Santino Knit Top
The easiest styling piece in your rotation.
FUCHSIA SHAW
The Robin Shirt
Size up for a looser finish.
Citizens of Humanity
Thassos Cropped Cotton Twill Cargo Pants
With a cropped shape and minimal details, these 100% cotton cargo trousers would look cool with a loose shirt and ballet flats.
Massimo Dutti
Leather Loafer
On a cooler day swap her flip-flips for a stylish pair of gathered loafers.
The Row
Park Medium Suede Tote
I can’t quite believe The Row’s Park tote is still in stock in this warm chocolate brown suede.
3. Casually Cool
Style Notes: When I first started looking for the best plaid shirt outfits, this Amaka Hamelijnck look [pictured above] stopped me in my tracks. Simple in its assembly (mid-blue denim Bermuda shorts, a white tank top and square-toe boots), it’s a master class in letting classic silhouettes and neutral colours shine. This is all about quiet confidence and unfussy finishes that have restraint but feel inherently cool.
Shop the Look:
I love how this diagonal plaid shirt looks styled with white, slouchy jeans and loafers.
This tank is highly regarded as one of the best on the market right now.
ZARA
Zw Collection Mid-Waist Denim Bermuda Shorts
Its not time to pack away your Bermuda shorts just yet.
ALOHAS
East Rift Leather Boots
Shop Amaka’s exact boots.
DeMellier
The Siena Bucket
4. Americana Fever
Style Notes: Arguably the easiest way to make a plaid shirt work in 2026 is to channel its rugged, western roots. In a look that wouldn’t feel out of place in Bella Hadid’s wardrobe, Tia Dewitt [pictured above] pairs a relaxed, orange-hued plaid shirt with straight-leg jeans and distressed cowboy boots for a look that feels straight out of the ‘90s Americana playbook. The icing on the cake? Well, that would have to be her Medallion belt. Simple yet striking, the sculptural buckle pulls her look together, adding a little extra polish.
Shop the Look:
4th & Reckless
Tove Check Shirt
Levi Strauss & Co.
501® ’90s Jeans
I’ve recently reignited my love for Levi’s 501 ’90s jeans, I mean they’ve been a fashion person bestseller for decades for a reason.
M&S
Cowboy Block Heel Pointed Toe Boots
Such a good price for a 100% leather boot.
Haven’t you heard? Medallion belts are all the rage this year.
Miu Miu
Aventure Nappa Leather Bag
Shop Tia’s exact Miu Miu bag.
5. Statement Street Style
Style Notes: If you’re a regular reader of Who What Wear UK, you’ll know that the layered top has been one of this year’s biggest trends. And as we turn the corner into autumn, we’ll be layering polos with plaid shirts. Don’t believe me? Just ask Sofia Mcoelho [pictured above]. Choosing to stack a cute pink shirt over a canary yellow polo, creates a dynamic finish. For a more casual, street-ready look, lean into slouchy jersey shorts, chunky trainers and a bold-coloured sock for a finish that’s guaranteed to go out with a bang.
Shop her Look:
Pull&Bear
Check Shirt With Pocket
No need to size up as this plaid shirt comes naturally oversized.
Lands End
Short Sleeve Supima Polo Shirt
Collusion
Baggy Longline Jogger Short
Wear again with a fitted V-neck top and loafers for a casually cool weekend look.
Adidas X Bad Bunny
Badbo 1.1
Shop Sofia’s exact trainers.
Uniqlo
Colourful 50 Socks
Uniqlo’s colourful sock range comes in 50 dopamine-inducing shades.
6. Pretty In Pattern Clash
Style Notes: If you’re a maximalist dresser looking to make the plaid shirt work hard for you this year, simply turn your attention to Karyna Balaban’s dopamine-inducing look [pictured above]. By mixing a playful prints with her strong check plaid, she creates a look that demands attention and holds your gaze. This is all about balancing business with the joyfully unapologetic, and what could be better than that?
Shop the Look:
Superdry
Check Flannel Boyfriend Shirt
Superdry have so many vintage-inspired plaid shirts in stock.
Source Unknown
Leopard Print Anouk Mini Skirt
You can now shop It girl favourite Source Unknown at Harrods in the UK.
If you like these boots, I’d be quick as H&M’s affordable shoe offering never stays in stock for long.
The Attico
La Passeggiata Medium Leather Tote
Aspinal of London
Freshwater Pearl Necklace
Pearls are a girls best friend.
7. New York or Nowhere
Style Notes: Perhaps the most ingenious ways I’ve seen a plaid shirt worn is often by New York natives. Layered underneath tank tops or worn backwards with the collar up to create a funnel-neck like Deva Pollon [pictured above], there’s something creative and cool about the way she’s reworked the classic. Playing with proportions, her sculptural midnight-blue barrel-leg jeans cast a striking shape, whilst her playful leopard-print bag and croc-effect heels dress things up—proof that a plaid shirt can be anything but predictable.
Shop her Look:
TIBI
Reversable Checked Cotton and Silk-Blend Shirt
H&M
Barrel Regular Waist Jeans
Id advise you size down in H&M’s barrel leg jeans as they tend to fit a tad oversized.
Season after season, Prada’s luxurious offering of Bonnie bags always make it to the top of my wishlist.
Tom Ford
Croc-Effect Leather Mules
The meticulous attention to detail on these backless, croc-effect Tom Ford mules will make these your go-to pair.
Saint Laurent
Lily Cat Eye Sunglasses
The easiest way to keep the winter sun at bay.








