Winona Ryder’s innovative yet classic style often lands her on coveted best dressed lists. Her eclectic taste and willingness to take fashion risks led Ryder to don vintage looks on the red carpet before it was cool and to take couture to the courtroom years before Naomi. To dress like Winona, you must dare to experiment and become a trend setter rather than a fad follower.

Combine the old with the new. Winona’s style trademark is adding a modern twist to vintage fashions. Ryder’s favorite vintage designers include James Galanos and Charles James, both famous for their evening gown collections.

Put a dark twist on the school girl look by mimicking Ryder’s “Heathers” character, Veronica. Pair pleated plaid skirts with boxy jackets and white button downs, accesorizing with funky tights and oversized brooches. Remember to stick with Veronica’s colors: blue, black and white.

Wear Marc Jacobs. Winona Ryder wore a black Marc Jacobs dress to her infamous shoplifting trial and later appeared in a series of ads for her designer friend’s apparel. Jacobs, like Ryder, enjoys blending glamour and grunge and masculine and feminine fashions.

Buy one of everything in black. Like her “Beetlejuice” character, Lydia, Ryder appreciates black clothing for its versatility, functionality and timelessness.

Mix it up. Comfortable in overalls and a tee shirt or ultrafeminine floral print dresses, Winona marches to her own fashion beat. In keeping with the actress’s individual style, create your own eclectic looks rather than mimicking hers.

Wear designer shoes or convincing look-alikes. Among Ryder’s favorite shoe designers are Stuart Weitzman and Manolo Bhlanik. If these brands fall outside your price range, visit department stores like Macy’s or discount shoe retailers like Payless.

Pay attention to the details. Whether working the red carpet or taking a casual stroll, Ryder clearly puts effort into achieving her polished look. Add a diverse collection of scarves, hats, coats, jewelry and handbags to your wardrobe to look put together from head to toe, just like Winona.


  • Shoe retailers, like DSW, sometimes sell high-end brands like Stewart Weitzman at affordable prices.

  • When on trial for shoplifting, Ryder received a lot of media attention for her courtroom fashion. Arguably, her wardrobe sparked more press interest than her crimes. Despite her guilty conviction, Ryder looked classy, pulled together and appropriate.