Wellies & Wild Nights: The Icons Who Defined Glastonbury Fashion

We can’t talk Glastonbury without mentioning Kate Moss. When she first appeared at the festival in the early 2000s, she set the standard. Her effortlessly cool, rock 'n' roll looks sparked trends that are still going strong two decades later – copied, pinned, and referenced year after year.

Her most legendary Glasto moment? Arguably 2005. In a look that became instantly iconic, Moss turned heads in tweed Alexander McQueen micro-shorts, a black waistcoat, and the now-famous Hunter wellies for a laid-back androgynous, yet impossibly stylish look. Suddenly, everyone wanted to look like they just threw something on and looked perfect. Add tousled hair, and oversized shades, and you've got the blueprint for cool-girl festival dressing.

Later that same weekend, Moss stunned again in a metallic gold sequinned tunic, paired (again) with her trusty Hunters and a cropped leather jacket. It was part disco, part muddy field, kicking off the “mud chic” aesthetic. Effortless, practical, and cool without even trying.

Then in 2008, she did it again. Moss was spotted in understated low-rise shorts, a simple black t-shirt, letting her vintage waistcoat shine – of course paired with tousled hair, oversized sunglasses, and her now-trademark Hunters. It looked thrown together — but every element was intentional. A little rock, a little glam, and completely iconic.

Style Takeaway: Comfort meets cool, don’t shy away from sparkle or statement pieces, and wear it like you mean it.

If Kate Moss was the original queen, Alexa Chung carried the Glastonbury torch into the 2010s with her unique blend of indie, and tomboy-meets-French-girl fashion. Her festival looks were never overly styled – just effortlessly nonchalant, and a little dishevelled.

It started with 2008, when she nailed the just-rolled-out-of-a-tent look. She wore cut-off denim shorts, a simple striped tee, and a leather biker jacket – a combo that’s since become a Glasto staple. Paired with messy hair, knee high socks, and welly boots - the ultimate cool-girl combo.

Fast forward to 2011, and she was deep in her indie sleaze era. Think fedora hat, slouchy military jacket, high-neck blouse, statement necklace, and smudged eyeliner. A bit sexy, but also keeping that tomboy vibe, a perfect reflection of the Tumblr cool-girl energy of the time.

Then came a major style switch-up in 2014, when she arrived in a stunning, silver lamé mini dress – a departure from her usual tomboy staples. She wore it with her usual ease, grounding the glam look with a simple green coat, knotting a staple grey knit around her waist, and wearing those ever-present Hunter boots, but this year in a cropped style.

Style Takeaway: Mix a little grunge with a little glamour, and always look like you’re not trying too hard (even if you are).

Before Pinterest boards were filled with crochet and cowboy boots, Sienna Miller was living the boho dream in a field at Glastonbury, setting the gold standard for effortlessly undone boho-chic. It all began in 2004 , when she stepped onto the Glasto scene with bedhead hair and barely-there makeup, wearing a tiered asymmetric dress, wide studded belt, and Uggs, paired with rave sunglasses, and the all-important VIP wristband. It was carefree cool at its best.

By 2010, her style had evolved but stayed true to its bohemian roots. That year, she wore cut-off denim shorts, a slouchy vest, and a crochet waistcoat. She topped the look off with lace-up ankle boots, a sunhat and an armful of vintage jewellery, keeping things playful but polished. It was grown-up boho, a little cleaner, but still full of character.

At Glastonbury 2013, her look was a masterclass in texture and personality: a richly embroidered tapestry-style jacket layered over a casual black tank and subtly patterned high-waisted shorts. She topped it off with a wide brimmed felt hat and rugged knee-high boots, adding a touch of vintage flair.

Style Takeaway: Layer textures and prints with confidence, and let standout pieces (like an embroidered jacket or a studded belt) do the heavy lifting. Add a wide-brimmed hat for instant cool.