1. The Hendrix Monterey Headband
Jimi Hendrix didn't just play guitar with his teeth; he defined a whole vibe. A patterned silk scarf tied around the forehead is a timeless nod to the ultimate showman. Rework it with a modern, minimalist print.
2. Janis Joplin’s Rose-Tinted Glasses
Before Instagram filters, there was Janis.
Her oversized, colorful lenses were part of her persona. Bring back the vibe with circular frames in an unexpected color like ocean blue or sunny yellow.
3. The Woodstock Tie-Dye
The original symbol of '60s counter-culture is more than a cliché. Instead of a full-body swirl, try a single elevated piece: a tie-dye bucket hat or a pair of high-end dyed socks peeking over your boots.
4. Stevie Nicks’ Mystical Shawl
Part of the Fleetwood Mac singer's on-stage magic came from her flowing, ethereal shawls. Update the look with a lightweight, sheer kimono in a dark floral or geometric pattern over modern basics.
5. The Punk Rock Leather Jacket
Pioneered at anti-establishment festivals in the '70s, the leather jacket is pure rebellion. Lighten it up for summer by opting for a cropped, vegan leather version or a jacket with painted details on the back.
6. Kate Moss’s Glastonbury Wellies
In 2005, Kate Moss made mud fashionable by pairing Hunter rain boots with tiny shorts. Even if it's sunny in Grant Park, high-end rubber boots offer a practical, chic edge to any festival look.
7. The Original Lolla Grunge Flannel
In the '90s, Lollapalooza was the epicenter of grunge, and the flannel shirt was its uniform. Wear a lightweight version open over a band tee or tied around your waist for that authentic anti-fashion statement.
8. Kurt Cobain’s White Oval Sunglasses
Those iconic white sunglasses were an instant statement. The shape has come back in a huge way. It’s a perfect, slightly alien addition to any outfit that says you know your music history.
9. Björk's '90s Space Buns
Long before they were a festival staple, Björk was rocking multiple mini-buns. It’s a playful and practical way to keep your hair out of your face while paying homage to a true original.
10. The 'Kinderwhore' Babydoll Dress
Popularized by Courtney Love, the babydoll dress paired with combat boots was a defining female grunge look. Make it modern with a sheer version layered over a slip or by choosing a dress in a luxe fabric like satin.
11. Daft Punk’s LED Glow
Their 2006 Coachella pyramid set was legendary, defined by futuristic, robotic lights. Integrate the idea subtly with LED-laced sneakers, a glowing piece of jewelry, or light-up fiber optic hair clips for after dark.
12. Amy Winehouse's Headscarf
Paired with her signature beehive, Amy's rockabilly-style headscarf was iconic. A simple folded bandana tied around the head is an easy, powerful nod to the late soul singer's unforgettable style.
13. Florence Welch’s Flowy Gown
Florence + The Machine brought ethereal, bohemian romance to the stage. Channel that energy with a maxi dress that moves, but keep it city-appropriate with combat boots instead of bare feet.
14. Beyoncé's 'Beychella' Hoodie
Queen Bey's custom Balmain hoodie wasn't just merch; it was a cultural statement. The modern takeaway is the elevated graphic sweatshirt. Find one from an independent Chicago artist or a brand with a message.
15. Harry Styles’ Sequins
His dazzling, gender-fluid sequin jumpsuit at Coachella proved that maximalism is back. You don’t need a full jumpsuit; a sequined top, shorts, or even a sparkly bucket hat can capture that joyful exuberance.
16. The Bucket Hat
A staple from '80s hip-hop and '90s rave culture that has become a festival necessity. It's practical sun protection that has been endlessly remixed. Find one in a bold color or with a unique texture.
17. The Band Tee
The ultimate classic. It shows your taste and is a built-in conversation starter. Instead of a vintage replica, grab official merch from one of the bands playing at Lolla this year, like The Smashing Pumpkins.
18. The Utility Vest
Rooted in rave and big beat culture, a vest with plenty of pockets is both a fashion statement and a solution to carrying your stuff. Look for a modern, streamlined version in a neutral color.
19. Animal Print Everything
From '70s glam rock to '80s punk, animal print has always screamed rock and roll. A leopard-print crossbody bag or snakeskin-patterned boots add an instant dose of attitude without overwhelming your look.
20. The Fringed Jacket
A little bit country, a little bit '60s psychedelia. Fringe adds movement and drama to any outfit. A black or tan suede jacket with fringe on the sleeves is a classic that always feels right at a festival.
21. Layered Chain Necklaces
Popularized in punk and '90s hip-hop, layering delicate and chunky chains adds texture to a simple tee or dress. It's an easy way to add a bit of edge and personality to your festival uniform.
