The 12th Annual MTV Video Music Awards (Photo by Ron Galella/WireImage)

The Mother of ‘Messy’: A Look Back at Courtney Love’s ’90s Style

Courtney’s wardrobe is up for sale this week, prompting reflection on her fabulously tousled, pre-glow-up look circa Hole.

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Dec 5 2018, 7:38pm

The 12th Annual MTV Video Music Awards (Photo by Ron Galella/WireImage)

Courtney Love’s wardrobe is up for sale at Heroine this Thursday. But don’t hold your breath, Hole fans: it’s Love’s well-heeled, grown-up collection of Hedi Slimane, Marc Jacobs, and Givenchy that’s being sold off to benefit charity, not her frayed gingham babydoll dresses or the Doc Martens that have been apocryphally attributed to her.

“I think that a wardrobe is a living, breathing thing, like, I’ve been known to talk to my dresses,” Love told Vogue. If only those dresses sit down for an exclusive interview with GARAGE! It’s hard to think of a celebrity whose outfits have been more scrutinized than Love’s over the years. She cuts an elegant figure these days, but back when her music career was first taking off in the early ’90s, Love’s style was a little more devil-may-care. Call it grunge, call it kinderwhore, call it whatever you want: whether hurling candy at Kathleen Hanna at Lollapalooza or whipping a compact at Madonna at the MTV awards, there’s no denying that Love pioneered and perfected the stylistic art of what we would today call “being messy.”

This inherent messiness of Love’s signature look—sheer slips and witchy velvet, cigarettes clutched dangerously close to her tousled blonde locks, words like “DIVA” and “WITCH” scrawled across her body in Sharpie—had such a powerful effect that, over 20 years later, rebellious teenage girls are still learning the lyrics to “Celebrity Skin” and pairing their Docs with long, frayed dresses. In a twentieth anniversary ode to the album Celebrity Skin, New Yorker staff writer Naomi Fry pinpointed Love’s dress at the 1997 Golden Globes as the look that “transformed Love from a chaotic, thrift-store-wearing avatar of the grunge era to a kempt, Versace-gown-clad star,” but we think her pre-Versace days deserve some love, too. In celebration of Love’s fashion legacy, let’s take a look back at some of her most powerfully messy, pre-glow-up fashion moments.

The Epitome of Babydoll (1994):

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Photo by Ron Davis/Getty Images

Love stepped out to a D.A.R.E. event featuring Richard Tyler’s fashion collection and the debut of a short film by Johnny Depp (has there ever been a more 1994 sentence?) in the defining Love-ian look: a ruffled babydoll dress accented with actual baby, “WITCH” scrawled on her arm in lipstick, and a jaunty purple ribbon belt tying it all together.

Sheer Slip and Cigarette (1990):

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Photo by The LIFE Picture Collection/Getty Images

Nobody, but nobody, wore a slip like Courtney.

Black Lace in Relief with Cigarette (1995):

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Photo by Mick Hutson/Redferns

A real Madonna vibe in this photo—which is ironic, given their history of antipathy. (Note the cigarette, pearl choker, and heart pin; the devil’s in the details.)

Butterfly Wings, Pink Tube Top, and “DIVA” Midriff (1990):

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Photo via Getty Images

In case you can’t make it out beneath her guitar strap, Love’s toned midriff reads “DIVA” in Sharpie. That, plus the butterfly wings and tube top, make her look like an extremely fashion-forward performer at a child’s birthday party.

White Silk and Tiara (1995):

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Photo by Time Life Pictures/DMI/The LIFE Picture Collection/Getty Images

It’s a kick to see Love, tiara-ed and wedding-attired, wearing matching silk with Amanda de Cadenet, seeing as the two would soon fall out. (Amanda’s comment on the split: “I, uh, don’t really have anything to say about that.”) Time flies when you’re having feuds!

Visible Bra and Glitter Hoops (1990):

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Photo via Getty Images

Love always found her light onstage, and this look—ruffles, hippie dress, black bra sticking out, hoops, bangs in her eyes—is pure, Hole-y radiance.

Sparkly Lingerie and Flower Crown (1999):

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Photo by Brian Rasic/Getty Images

This look marks the tail end of Love’s fabulously messy ’90s ensembles. Here, she serves up one last glittery, fishnetted, Sharpie-scrawled gasp at Glastonbury before going through it for a good chunk of the 2000s, only to emerge a Hedi Slimane-clad swan.

Tiny Hat and Breakfast Buffet at Planet Hollywood (1990):

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Photo by The LIFE Picture Collection/Getty Images

Love serving herself scrambled eggs from the Planet Hollywood breakfast buffet is the last image I want to see before I die. For more gourmet Courtney food content, read her 2012 Grub Street diary—you won’t be disappointed. Sample entry: “Every day I have my house manager, Hershey—who I stole from the Mercer Hotel with André Balazs’s blessing—wake me up with a hot washcloth for my face, a leg rub, and a plate of toast soldiers.”