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Iconic Androgynous Ladies of the ‘90s

Before the ultra-inclusivity and gender politics of the digital age, queer people rarely had a presence in pop culture. Coming out was an act usually met with reluctance, if not complete ostracism. So, growing up queer often meant role models were hard to find.

As children of the ‘90s and earlier generations, we’ve found icons in Britney and Beyoncé to help us through our toughest queer times. But even before we had the inkling, there were certain celebs who nudged us in that direction. Such bold women tested the boundaries of gender expression well before it became the borderline social norm it is today. Although men like Bowie and Prince were accustomed to this practice, it was women like these who demanded a man’s power with their subtle characteristics that may have just appeared to be a trend at the time.

Angelina Jolie

This chameleonic performer has taken many forms throughout her illustrious career, from assassins to mothers. But we remember first seeing her in the 1995 cult classic,Hackers. Sporting a neo punk look with her short cut hair, she dominated a male-driven underworld with her tech genius.

Chloë Sevigny

A muse to many, she sported a boyish charm even through her Manhattan “it girl” persona. With her iconic pixie cut, she stole the screen in her breakout role as an HIV+ teen in Larry Clark’s 1995 cult classic,Kids. Since then, she’s gone on to push many boundaries both in her personal life and her film career.

Eve

Of the many iconic female rappers of the ‘90s, Eve has always exuded a sex appeal that speaks to fans of all gender identities and sexual orientations. And in a male-dominated industry often known for manufacturing misogynist lyrics, she’s held her own with a badass repertoire of tracks.

Jada Pinkett

Although today she’s known for mothering some of the most visible gender fluid kids of our time, she had her own androgynous style at the dawn of her career. Often sporting a short do and playing with societal norms of fashion, she made plenty question their inclinations from an early age.

Joan Chen

Although she may not be a household name, this Chinese actress personified androgynous sex appeal during the ‘90s. Fans ofTwin Peakswill recall her short, slick do with her angular power suits as she took over her husband’s business, among other professional interests.

Kate Moss

If there’s one supermodel of the ‘90s who defined the decade’s subtle inclination for androgyny, it would be Kate. From her edgy Calvin Klein campaigns to her own grungy style and angular features, she set the standard for a certain kind of non-binary beauty that’s still idolized today.

Missy Elliott

From her velour tracksuits to her finger waves, this raptress has long set herself apart with a certain sense of style. And with a repertoire of some of the most iconic tracks of our time, she could make most men in her industry shake in their boots.

Robin Tunney

Although she’s been known to play the typical pretty girl on more than one occasion, one of her most iconic roles was that of a troubled teen in the 1995 hit,Empire Records. The outcast of the group, she shaves her head after getting fed up with her boyfriend. The role remains in our queer hearts to this day.

Sinéad O’Connor

Long before Miley’s often problematic creative expression took over pop culture, this Irish rock star sported a shaved head while churning out iconic ballads with her angelic voice. Known for a shocking stunt onSNL, she’s always been outspoken. In recent years, she’s been very vocal about her mental health, raising concern and awareness.

Winona Ryder

Another ‘90s darling, this actress defined her generation. Known for films likeReality BitesandGirl, Interrupted, she was America’s edgiest sweetheart. And with that gender-fluid sex appeal, she’s played the object of affection for many of America’s boys and girls.