Winona Ryder ’90s style: 8 of her most iconic outfits that made her a defining fashion icon

If one outfit explains the endless appetite for ’90s off-duty cool, it is this one. At the 1991 premiere of The Commitments, Winona Ryder paired an old Tom Waits T-shirt with a lapelled leather jacket and light-wash mum jeans, a formula that still fills moodboards. A band tee, leather jacket and straight-leg denim remain a foolproof uniform today, and Ryder’s version is still the reference point.

Winona Ryder wore a deep purple, sleeveless velvet dress to the New York premiere of The Age of Innocence at the Ziegfeld Theatre in September 1993, arriving with then-boyfriend Dave Pirner of Soul Asylum. Martin Scorsese’s adaptation of Edith Wharton’s Gilded Age novel cast her as May Welland and earned her an Oscar nomination for best supporting actress. Velvet suited the film’s period mood, and the rich colour stood out against the black that dominated her red carpet wardrobe.

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Winona Ryder attended the 66th Academy Awards in March 1994 as a nominee for The Age of Innocence. She chose a fitted off-white slip dress with a flapper-style fringed hem. The slip-dress cut kept the 1920s nod from reading as costume, giving the fringe a distinctly ’90s attitude. Against her goth reputation, the airy look came as a surprise.

Winona Ryder returned to the Oscars for the 68th ceremony in March 1996 in a beaded blush gown by Badgley Mischka, worn with a shawl. Designer Mark Badgley has recalled that he and partner James Mischka dip-dyed the dress in their kitchen sink the night before, after Ryder asked for blush. Her hair was just as considered: a close-cropped, light-blonde cut set in vintage-inspired finger waves, with a soft pink lip.

In 1998, Winona Ryder dressed up for the Film Society of Lincoln Centre’s tribute to Martin Scorsese, the director who had cast her in The Age of Innocence. She chose a sheer lace gown and brought back her signature red lipstick, pairing it with another short, closely cropped haircut. The look is all contrast: sheer lace set against a bold lip and a sharp crop. It is proof that a strong beauty note can anchor an entire evening look, and a reminder of her short-hair era.

Winona Ryder dressed in pink for the American Film Institute’s Lifetime Achievement Award salute to Martin Scorsese in 1997, a bright break from the black she usually favoured on the red carpet. Her strappy satin gown had a square neckline and a slim column skirt, topped with a sheer pink wrap draped across her elbows. A red satin clutch clashed boldly with the pink, while a bracelet and drop earrings added shine. Her short crop and red lipstick kept the sweet colour from reading too soft.

One of Winona Ryder’s rare forays into colour came at the New York premiere of Smoke Signals. She wore a knee-length pale blue A-line dress with a boatneck and a fitted shape, finished with silver sandals. The soft shade and clean silhouette felt a world away from her black-heavy red carpet record, yet it was no less distinctive. The silver sandals added a modern shine to a dress that kept everything else deliberately simple.

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