Winona Ryder's Style Evolution Through the Years

Ryder kept it cozy and casual for the Amazing Chuck and Grace premiere. The look she went for included a printed maxi dress and an oversized gray wool overcoat. In addition, her fringe bangs added the perfect amount of edge.

The actress smiled alongside actor Rob Lowe at the Golden Globe Awards in a red velvet dress matched with a boxy black blazer. Her red lipstick and small beaded necklace were nice touches to the elegant ensemble.

Ryder has always been the queen of street style. She’s pictured here with the Beastie Boys’ Ad-Rock wearing a slouchy light pink sweater, dark wash jeans, and a simple black flap handbag.

Ryder proved less is more when she arrived at the Independent Film Spirit Awards in a simple white dress with a flouncy pleated skirt. And, yes, that’s Keanu Reeves beside her.

The actress donned a sleek and structural blazer dress paired with sheer tights for the premiere of Batman.

For a 1989 music video titled “Debbie Gibson Is Pregnant with My Two-Headed Love Child,” Ryder was put in a silky bridal gown complete with veil.

Ryder posed with her Edward Scissorhands co-star in a black leather trench coat layered over sheer black stockings. She styled the all-black sartorial statement with a dark red lip and a chic black bob.

You can always count on Ryder to wear something innovative or unexpected to the red carpet. She was at the Dracula premiere wearing a ruffled two-piece skirt set in a soothing dark blue hue. The outfit had a specific Victorian-era feel to it.

She attended the Age of Innocence red carpet in another vampy look. This one included a deep purple velvet dress with a simple choker and minimal makeup.

How amazing is this fringed gown she wore to the 1994 Oscars?

She sported more velvet at the premiere of Little Women. This time, it consisted of a hip-length velveteen jacket layered over a voluminous black skirt.

Ryder looked like she stepped right out of an old Hollywood movie when she showed up to the Fire and Ice Ball in a timeless black gown with an exquisitely designed neckline and fitted waist.

She rocked a similar look at an event in Los Angeles. Ryder paired a gown with oversized pearl and diamond earrings and a slicked-back updo.

For the Academy Awards, she went with a flapper-esque ensemble that consisted of a sequined chiffon beige dress with a matching stole. Her wavy hair and satin pouch handbag made things look extra romantic.

Here, Ryder wore a Barbie pink satin gown with a chiffon shawl, statement-making diamond earrings, and a rose pink envelope clutch.

The actress can never say no to a head-turning lace look. This dress featured a ruffled see-through collar and a sparkly skirt.

The Cannes Film Festival always has fantastic looks, like this sequined getup Ryder wore with shiny silver sandals and a bedazzled hair accessory.

Here’s Ryder in another excellent Cannes Film Festival ensemble comprised of a purple gown matched with a chiffon stole, a layer of necklaces, and a beaded handbag.

For the premiere of Smoke Signals, the actress stepped out in a pretty periwinkle dress with a high neckline and slightly ruffled hem.

She wore an all-black look for the 1998 MTV Music Video Awards. It featured a sleeveless top, satin pants, and square-framed sunglasses. Her platform flip-flops and sweater tied around her waist gave her an effortlessly cool vibe.