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The enduring pull of ’90s fashion lies in its simplicity. While trends come and go, the decade’s signature silhouettes have never really gone out of style. With Love Story putting Carolyn Bessette-Kennedy back into the spotlight, and a renewed fascination with the decade of the supers—Kate Moss, Naomi Campbell, and Cindy Crawford—the pull of those years feels stronger than ever.
As a nineties baby whose gateway into fashion was TV and film—like many of my peers, I grew up watching on Friends and Sex and the City, obsessing over the costumes in Pretty Woman and The Talented Mr. Ripley. It’s the high-profile women of the time whose particular brand of effortlessness I’ve always been drawn to, and still reference in my own wardrobe.
How to Get the ’90s Look:
Among the great ’90s staples that have retained their cultural capital today are the slip dress, the cigarette jean, and the pencil skirt. There’s also, of course, the jersey dress and top, and the itty bitty cami. And let’s not forget about the strappy heeled mule. These were all mainstays in my closet then—and now.
What makes these specific styles hold onto their currency is not just nostalgia, but function. Simple, elegant, and inherently versatile, the magic of ’90s was its authentic expression of personal style. It preceded the algorithmic sameness that flattens taste today, teaching me that true style is knowing how to wear your clothes—not have your clothes wear you. Let’s take a closer look at the decade’s defining pieces that still hold up.
The Slip Dress
Cut on the bias with spaghetti straps and a subtle V or cowl neck, the slip dress is classic for a reason. Its pared-back elegance appealed to style icons of the time—Princess Diana, Kate Moss, Gwyneth Paltrow, and Jennifer Aniston—for its polished refrain. Even Carolyn Bessette-Kennedy’s wedding gown, which was fitted at the hips and puddled lightly on the floor, was a slip dress. Today’s It girls (Zoë Kravitz, Alexa Chung, and Dakota Johnson) continue to gravitate towards the silhouette, in simple neutrals and more romantic takes (in pastels with lace trims), for date-night dressing, press tours, and beyond.
Calvin Klein
Lynn midi dress
The Cigarette Jean
Cigarette jeans (a.k.a. straight-leg, high-rise fits) were mainstays in the off-duty wardrobes of CBK, Cindy Crawford, and Winona Ryder for their undone ease. Style yours now the way Crawford or Courtney Cox might with low-heeled boots and a black leather belt.
Levi’s
wedgie straight ankle jeans
Re/Done
90s straight-leg jeans
The Slinky Jersey
This soft, often, fluid fabric skims the body with ease, delivering that rare combination of comfort and allure that defined the low-key mood of the decade.
Kallmeyer
Jocelyn draped top
The Heeled Mule
There’s no denying: Strappy mules were the most popular shoe silhouette of the ’90s. Forever tied to the decade, they remain relevant today, whether paired with slip dresses or denim.
Manolo Blahnik
Haribalmu sandals
The Pencil Skirt
Synonymous with ’90s Calvin Klein and a favorite of Princess Diana, CBK, and Gwyneth Paltrow, the pencil skirt holds its place as a power piece that goes beyond the workwear rotation into late-night cocktails and red carpet appearances. The skirt suit set made a triumphant return on the spring 2026 runways, matching at times, but far from a must.
J.Crew
Trouser pencil skirt
The Cami
The cami is ’90s version of the tank top: an everyday basic that works overtime during spring and summer. Pair with a denim and oversized shirt, or a slip skirt and matching cardigan—a way it was often worn on the red carpet. Choose from square or scoop necks, and stick to thinner straps.
