FLANNELS THINKS:
From Glastonbury to Coachella, Moss to Hilton, we chart the making of festival fashion and the looks that’ll go down in history.
Kate Moss in a shimmering gold mini dress. Kylie Jenner – at the height of her King Kylie era – all flower crowns, electric blue hair and high-tops. Paris Hilton in barely-there bikinis. And Robbie Williams and Oasis partying together at Glastonbury '95, at the height of Britpop power. Google ‘iconic festival outfits’ and you’ll be rewarded with images of crochet, glitter, low-slung belts and fringing. Lots of denim. Lots of wellies. Lots of personality.
Festivals have become synonymous with ultra-fun, out-there outfits that are a much-needed departure from our day-to-day looks. A place where the normal rules of dressing go out the window. Where party dresses are paired with waterproofs and waistcoats with muddy wellies. A place where people feel free to be themselves. It’s bred the ultimate high-low aesthetic, where form and function are of equal importance.
From Glastonbury to Coachella, Moss to Dean, and the eras we’d rather forget, we chart the making of festival fashion and the looks that’ll go down in history…
We have a lot to credit Woodstock for. A one-time phenomenon that has etched itself into our collective minds - and our festival wardrobes. A reaction to the political turmoil in America, it was a moment to break free, to be with like-minded people in a safe space. Long before we were freeing the nipple on Instagram, the Woodstock set were painting their bodies with flowers in the ultimate act of self-expression. The looks? It was 1969. Think denim cut-offs, waistcoats, fringing and headbands and floppy hats. Aka, festival style that still reigns supreme.
During the ‘70s, festivals became a moment of rebellion and reform once again. But the free-loving spirit of the ‘60s gave way to the anti-establishment punks of the ‘70s and the festival attire? It matched. Bare feet were replaced with chunky Dr Martens. Inspired by Vivienne Westwood and Malcolm McLaren’s iconic boutique, SEX, leather jackets were decked out with safety pins and metal studs. Both still firm fixtures of today’s festivals.
The ‘90s, aka our favourite era of fashion right now, brought us the glory days of Britpop. Blur. Oasis. Pulp. Suede. Whilst its influence has been everlasting on the music industry, it also played a big role in our wardrobes.
The British answer to America’s grunge moment, it was filled with baggy jeans, bucket hats, Stone Island windbreakers, zip-up jackets and adidas sneakers. It was Robbie Williams ditching his boy band looks of Take That and partying with the Gallagher brothers at Glastonbury ‘95, decked out with bleach blonde hair and that now iconic red zip adidas jacket. No wonder he’s hot on the Oasis reunion heels with a smartly titled new album called Britpop…
But the period that will go down in festival-dressing history, that conceived ‘festival dressing’ as the phenomenon we know today? That would be the Noughties. Thanks in no small part to its icons: Paris Hilton and Kate Moss.
Coachella 2009 found Paris Hilton in her in-between era - post The Simple Life, pre-My New BFF - and looking exactly how you’d expect an off-duty heiress to dress for the desert. The formula was deceptively simple: green sweats slung low, a barely-there bikini top, outsized sunglasses, and a flash of metallic at the arm; it shouldn’t quite work, and yet it does. It reads casual, but don’t be fooled - this is strategic dressing from someone who insists she’s not a shopaholic, just helping the economy.
A year later, Kate Moss brought a whole wardrobe of festival looks that would forever go down in Glastonbury’s history books. Arm in arm with Pete Doherty, she traipsed through mud in a shimmering gold mini dress; tiny hot pants and an impeccably tailored waistcoat; studded jackets and trilby hats – all accompanied by a pair of filthy Hunter wellies. It was a turning point in festival dressing: wellies were no longer the reserve of the country set and Moss was to become synonymous with festival style forever more.
Moss might get the credit but look back to Woodstock and you see those same pieces - waistcoats, fringing and denim - in full force. It’s a formula that’s been referenced ever since.
Scroll through videos of Olivia Dean performing ‘Man I Need’ or ‘Nice to Each Other’ and you’ll find two constants: vibes are electric - and the comment sections keep pace. One reads, “She’s so refreshing.” Another cuts straight to it: “Her stylist loves her.”
That synergy is hard to fake. With Simone Beyene at the helm, Dean’s wardrobe works in harmony with her sound - think sequined dresses made for movement, sharp little skirt sets, and romantic, retro-inspired shapes that feel deliberate rather than costume-y. Add in that ever-present onstage wind machine - lifting her hair, catching the fabric just so - and the whole thing takes on a sense of motion that feels entirely intentional. The cherry on top? The soundtrack that goes with it.
In recent years, festival dressing has been trying to find itself once again. Kendall Jenner, Kylie Jenner and Hailey Bieber et al have chosen to shun the out-there ensembles they became renowned for at Coachella in favour of laidback, under-the-radar looks that could have been thrown on to nip to the shop for a pint of milk. The response? Well, it was tepid. Festivals should be fun and free and full of self-expression, the people (on TikTok) cried. It seems our obsession with a celebrity festival look isn’t waning.
First on the scene in the mid-2000s, Lilly Allen’s on-stage style felt delightfully chaotic - occasionally questionable, but ultimately quite chic. She made her mark in prom dresses and trainers, complete with neon eyeliner and chunky chains.
By the 2010s, it all got a bit tidier. Think sleek cuts and vintage touches, a style she still feels at home in, and one she’s continuing to refine on her current West End Girl tour, with a string of summer appearances lined up including Mighty Hoopla. She brought exactly that to Glastonbury during her one-off link-up with Olivia Rodrigo: side part in place, jewellery doing just enough, and a cropped monochrome jumpsuit that fit perfectly. If there’s one thing the British nepo kid knows, it’s how to own a stage.
From Disney Channel darling to bona fide rockstar, Olivia Rodrigo’s style evolution has taken a decidedly pop-punk turn in the decade since she first appeared on screen. These days, the 22-year-old Grammy winner gives equal star power to a casual paparazzi snap in a plaid miniskirt and platform boots as she is walking down red carpets in couture gowns.
She brought that same energy to Glastonbury, nodding (whether intentionally or not) to Geri Halliwell’s iconic Union Jack moment - arguably one of British pop’s most indelible fashion moments - with her sequined hot pants; it’s a bold callback - but then, she rarely plays it safe.
And with 2026 marking the anniversary of the Spice Girls’ ‘Wannabe’, that irreverent energy feels newly relevant - Rodrigo tapping into a pop lineage that still shapes festival style, and signalling a return to nostalgic, statement-led looks set to follow.
And now? Glastonbury rests, but the party goes on - Burning Man, Coachella, Tomorrowland, Download. Festivals known for jaw-dropping style, mud-drenched chaos, and attendees who refuse to let a little dirt get in the way of a killer look.
So, what festival outfits should you be rocking in 2026? Across festivals worldwide, this year’s looks are fuelled by Zara Larsson’s Midnight Sun Tour: experimental eyeshadow and brightly hued co-ords are set to feature heavily.
On the opposite end, Britpop is back. Olivia Dean’s vintage-inspired hits are sweeping the BRIT Awards and pop playlists, Harry Styles’ gender-fluid tailoring is making waves, and Lily Allen’s West End Girl era and tour add another creative thread. Think oversized scarves, bold brights, feathered touches, and statement eyewear.
Meanwhile, football mania-inspired style is back this summer, riding the wave of a certain football tournament set to take over festivals for months to come. Think football-themed shirts, Adidas Sambas, and sporty shorts - a playful nod to Robbie Williams at Glastonbury ’95. We’re here for it.
One festival stalwart, denim shorts, has been reworked for SS26, now coming in longer, Bermuda-style cuts. In jorts we trust.
But the most important part of festival dressing? Having fun. Feeling free. And honestly, not giving a f**k what anyone else thinks.