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The most iconic Glastonbury looks of all time

From Kate Moss’ Hunter wellies to Alexa Chung’s Barbour jacket here are the best ever Glasto outfits to inspire your festival look...

glatonbury best outfits
Natalie Salmon
Natalie SalmonFashion Digital Editor
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The world’s most famous music event is once again upon us. Yes it’s Glastonbury time, the UK festival never fails to deliver when it comes to the style stakes. After being cancelled two years in a row it made a triumphant return in 2022, with headliners such as Billie Eilish and A-listers including Sienna Miller turning Worthy Farm into their very own runway. 

This year is set to be an equally incredible year for music fans, with hundreds of acts performing between Wednesday the 21st and Sunday the 25th of June. Highlights this year include Sunday night's headliner Elton John, and Indie-sleaze icons Arctic Monkeys who make a Friday night appearance on the legendary Pyramid stage, followed by  Guns N’ Roses on Saturday.

When it comes to ‘Festival style’ few music events are as iconic for inspiration as Glastonbury. From Kate Moss’ Hunter Wellies to Alexa Chung’s Barbour jacket - fashion trends are made and set in Somerset's rolling hills. With weather set to take a turn for the rainy it seems that the world’s muddiest catwalk is returning, so we made note of all the outfits that live in our mind rent free...

The 12 most iconic Glastonbury outfits of all time: 

Kate Moss - Glastonbury 2005

kate moss glastonbury

 The gold dress, the wellies, the rockstar boyfriend. No image of wellington boots is more etched in our memory than that of Kate Moss walking arm in arm with Pete Doherty at Glastonbury in 2005, bare legs out and dark navy Hunter wellies on.The look became so iconic that apparently it saved Hunter from going into administration, thanks to a dramatic sales increase.  Today the British heritage brand continues to enjoy the Moss-effect and is popular for festival goers and farmers alike. Fast forward to 2022 and Chanel’s AW22 wellies dominated their runway show during Paris Fashion Week, proof that the rain boot is going no-where this season. 

Alexa Chung - Glastonbury 2015

alexa chung glastonbury

One of the most iconic looks ever to hit the festival was Alexa Chung in double denim and her oversized Barbour coat. Once a staple of farmers and country bumpkins, Alexa made the humble wax jacket a must-have item for the festival set. 

Sienna Miller - Glastonbury 2004

sienna miller glastonbury

 Sienna Miller’s boho chic outfits will always be remembered, as she dominated the satorial agency for most of the early 00’s thanks to her signature boho-chic aesthetic. One look in particular will always be remembered for being the look that put her on the map and made all of us want a slow slung leather metal stud embellished belt. She paired this now iconic accessroy with a black denim tiere-ed skirt mini dress complete with neon aviators and short folded over micro-uggs.

RELATED: The 10 best bucket hats for festival season

Poppy Delevingne - Glastonbury 2016

poppy delevingne glastonbury

Another reigning Glastonbury style queen is non other than supermodel Poppy Delvingne, we went crazy over her short flower print dress and oh-so coveted aviator jacket combo. She nailed the model-off duty look. 

Cressida Bonas - Glastonbury 2013

cressida bonas glastonbury

 Cressida Bonas’ dungarees had us all reaching into the back of our wardrobes to find our very own to recreate the look. Pairing the look with statement sunglasses and a scrunchie, the actress perfected the relaxed attire which wins in the style stakes in Somerset.

Rita Ora - Glastonbury 2014

rita ora glastonbury

 Singer Rita Ora paired her cow print dungarees with Dolly Parton-esque white cowboy fringe boots. The look was teamed with a red sude handbag. A classic Glastonbury moment which set the cow print trend for years to come. 

Florence Welch - Glastonbury 2010

florence welch glastonbury

 Florence Welch from Florence and the Machine showed off her trademark ethereal style in a floaty ruffled maxi dress at Glastonbury in 2010. She teamed the look with a gold name necklace. 

Margot Robbie - Glastonbury 2017

margot robbie glastonbury

 Australian Oscar-winning actress Margot Robbie donned yellow Fear and Loathing in Las Vegas style aviators, worn with a Mickey Mouse  long sleeved t-shirt. Worn with leggings and the de rigeur wellies - the actress look was efffortless festival fashion at its best. 

Emma Watson - Glastonbury 2010

emma watson glastonbury

Who can forget Emma Watson’s studded Christian Louboutin boots she rocked to Glastonbury the perfect accessory for trudging around the fields - teamed with a camo-print corset top. The actress made her rare appearance to the festival back in 2010.

Kate Moss - Glastonbury 2005

kate moss 2005 glastonbury

 Yes this is the second time the model makes the list of most iconic outfits, but who can forget her micro shorts she wore to Glastonbury back in the same year, 2005. Suddenly there was nothing we wanted more than a waist coat and low rise ultra short shorts. Thanks for the memories Kate. 

Mia Regan - Glastonbury 2022

GLASTONBURY, ENGLAND - JUNE 24: Mia Regan is seen on Day One of the Glastonbury Festival on June 24, 2022 in Glastonbury, England. (Photo by Mark Boland/Getty Images)© Mark Boland
Mia Regan

Mia Regan was spotted on day one of Glastonbury Festival on June 24, 2022 wearing the ultimate Brit-pop essential - a Union Jack tee. Paired with bright red wellies and a denim micro-mini skirt, as well as 1960s mod-approved sunnies; she flew the flag for exceptional style. Mary Quant would approve.

Alexa Chung - Glastonbury 2022

GLASTONBURY, ENGLAND - JUNE 24: Alexa Chung is seen on day one of the festival wearing her vintage Barbour jacket on June 24, 2022 in Glastonbury, England. (Photo by David M. Benett/Dave Benett/Getty Images)© David M. Benett
Alexa Chung

Perennial Indie-sleaze style queen Alexa Chung wore her signature vintage Barbour jacket to Glastonbury 2022, paired with an electric blue mini shift dress and knee high black-lace up boots that were made for walking... (and by that we mean walking backstage of course.)

Poppy Delevingne - Glastonbury 2023

Poppy Delevingne wears Nobody's Child© Getty
Poppy Delevingne

Poppy stepped out on day three of the 2023 festival proving the power of a high street number. She wore the coolest crochet mini dress from cult-adored label Nobody's Child. She paired with some classic Hunter wellies, and added a touch of cowgirl-core with a black tassled side bag.

Lily James - Glastonbury 2023

Lily wore a low slung mini dress with a Barbour jacket and wellies© David M. Benett
Lily James

Lily schooled us in understated festival glam, wearing a black ribbed mini dress that boasted gold netting around the cowl neckline and the hem, with a daring thigh split that allowed lace panelling to peek through. Channelling her inner Alexa Chung with accessories, she paired the glamorous mini with one of Barbour's iconic wax jackets and black ankle boots. 

Sienna Miller - Glastonbury 2023

Sienna Miller attends day five of Glastonbury wearing double denim and white cowboy boots© Mark Boland
Sienna Miller

Double denim was back with a bang for the 2023 festival. Glastonbury royalty Sienna Miller did what she does best and oozed festival chic in a cropped embellished denim jacket from Self-Portrait paired with high rise denim shorts from the same label.

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