Winona Forever: Winona Ryder’s Style Evolution

Attending the All-Star Tribute to Kareem Abdul-Jabbar in 1989, a fresh-faced Winona Ryder rocks a satin slip-style dress beneath an oversized blazer. Flash-forward to 2019 and this is the fashionista uniform of the moment.

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For the 1989 premiere of Great Balls of Fire, Winona Ryder channeled her character from Heathers and stepped onto the red carpet in a gorgeous off-the-shoulder white dress, with sheer long sleeves, stockings and sweet kitten heels to match.

How very.

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Full of the teen angst you’d expect from 90’s youth, Winona Ryder serves it right up — in androgynous style. Forever ahead of the trends, the young actress played up the masculine suit bit, complete with dress shoes, chunky ankle socks and an oversized white tee. If that wasn’t enough to fall in love with her style, have a look at that retro suitcase — yes, Winona!

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On the arm of then-beau and co-star Johnny Depp, Winona Ryder, dressed in head-to-toe black, hit the premiere of her film Edward Scissorhands in 1990. From the sheer details and red lipstick to her fringed bag, Ryder is serving up all the old trends that are new again in 2019. Minus the bad-boy-boyfriend, of course — because who has time for that?

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For the New York premiere of Little Man Tate in 1991, Winona Ryder rocked an oversized two-piece suit, complete with wingtips and effortlessly-perfect undone hair. Finishing it off with her signature red lip, Winona cements her status as the “it-girl” of the style scene.

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Sporting belted straight-leg jeans, a graphic tee, leather jacket and combat boots, Winona Ryder is the cool “fashion girl” we all aspire to be while attending a premiere in Hollywood in 1991.

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Switching gears from the usual all-black ensembles, Winona Ryder had some fun with colour in a blue corseted dress with lace trim — appropriately Victorian-inspired for the 1992 Hollywood premiere of Dracula.

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Winona Ryder ensured all eyes would be on her at the 1994 Academy Awards when she glided onto the red carpet in a floor length white (shocker!) gown with heavy beading and fringe details. Keeping it edgy, the petite actress rocked a pixie cut hairstyle and bold lip.

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Steeping outside of her comfort zone yet again for the Academy Awards in 1996, Winona Ryder opted for a beaded blush gown, styling her pixie-cut hair in glamorous retro-inspired waves.

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This is what we love about Winona Ryder’s style sense — she’s able to take a classic strapless gown in a colour that we’ve seen on her time and again, and still manage to make it look elevated in some way. From her chic chignon, bold red lip and that daring neckline, it all just works on Winona.

Rocking pink on the red carpet, Winona Ryder accessorized her strappy satin gown with a fuchsia clutch — if this isn’t a futuristic nod to the red-carpet vibes of present day, we don’t know what is.

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Lady in red Winona Ryder looked stunning in an off-the-shoulder red gown while attending a benefit event to honour Richard Gere in 2004. This shade was perfect on Winona, and the draped fit flattered her petite frame beautifully.

Wearing a long tweed jacket over a black dress, Winona Ryder styled her lighter locks in soft waves with natural makeup and minimal accessories.

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Not every fashion risk pays off, and Winona Ryder’s bohemian-inspired ensemble for the 2004 Los Angeles Film Festival is proof of that. While we love seeing Winona in colour, this mish-mash of prints, layers and proportions seems to overwhelm the actress’ small frame.

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Winona Ryder donned a strapless blush-pink gown with a ruffle-detail neckline to the 2008 Marie Claire Prix De La Mode Awards. With minimal accessories and soft makeup, this look was perfect on the actress, who’s penchant for the perfect strapless gown seems to get her on the best-dressed lists every time.

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Almost as fun to watch as her red-carpet style is Winona Ryder’s off-duty fashion. Forever the “cool girl” in Hollywood, Winona Ryder looked edgy and on-trend in distressed denim, a plaid shirt, fitted blazer and newsboy cap.

Donning an all-black outfit, Winona Ryder was buttoned up and all business in a suit, with silver accessories and a black clutch for the New York premiere of Black Swan — we’re not sure if we love or hate this one, but either way, Winona Ryder is definitely making it work.

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A longtime-fan of designer Marc Jacobs, Winona Ryder stunned at his fashion show in 2015 in a little black dress with strappy details. A simple cut and classic fit, the dress looked phenomenal on the actress, who manages to work the LBD so well that we forget it’s almost never in colour.

As signature a style move as her love of black, Winona Ryder is all about a touch of whimsy. Sporting a fun graphic sweater with patent loafers, the Stranger Things star looks as fresh-faced as ever, always managing to stay current while still staying true to her unique personal sense of style.

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In the perfect leather jacket, graphic tee, long skirt and chunky boots, Winona Ryder would be on-trend in the 80’s or present-day. With a seemingly timeless pulse on lasting trends and the styles that flatter her the most, Winona is grunge-glam forever, and we can’t get enough!

You’d think by now we’d be sick of seeing Winona Ryder in a strapless black gown — but you’d be wrong. There’s no one else who could make this classic style look quite so stylish. In her signature colour with loose waves and natural makeup, the Stranger Things actress serves up everything we’d hope for in a red carpet moment.

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Rocking her signature style at the Stranger Things 3 premiere in 2019, we’re placing our bets that the coming years will have us feeling inspired by a whole new crop of perfect LBD’s courtesy of everyone’s favourite edgy it-girl.

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