Winona Ryder is one of the most iconic actresses of all time. She’s effortlessly played complex female characters in dark cult movies such as Beetlejuice, Heathers, and Girl, Interrupted, as well as slice-of-life films such as Lucas, How to Make an American Quilt, and Mermaids. More recently, she reached younger audiences as the tireless Joyce Byers in Stranger Things. Put her in any role, and she’ll charm you softly with or without a chainsaw.
Besides being an incredibly talented actress, Winona has also blessed us with the chicest outfits in film and television. Her style, much like her roles, covers a wide range of trends. The world first got to know her darker, edgier sensibilities through her sleek outfits as Lydia Deetz in Beetlejuice and Veronica Sawyer in Heathers. Over the years, her look softened for How to Make an American Quilt’s Finn Dodd and Joyce Byers, who are more vulnerable characters. Whatever role she’s in, we can always get an accurate first read of her character through her sartorial choices.
This year, we’re celebrating her 47th birthday by sharing how you can pull together her most stylish onscreen outfits. Grab your wide brim hats, Christmas lights, or your choice of a Winona film prop—we’re about to style it up.
The heading-to-a-party outfit in Heathers
Heathers (1988) is full of timeless Winona Ryder looks that work even in today’s context. Right before heading to a party, Veronica grabs some snacks and makes small talk with JD, who hasn’t yet revealed his psychopathic tendencies. We’re loving how she pairs a gray off-the-shoulder sweater with a black suspender dress for an effortlessly chic look.
Off-the-Shoulder Sweater, $24.99
Thick Strap Pinafore Skirt, $15
The inadvertently conspiring murder with your boyfriend look in Heathers
It’s all fun and games until your boyfriend tricks you into murder. Well, if you’re going to inadvertently break the law, you might as well do it in style. Here, Veronica’s wearing an ensemble that consists of a knit bomber jacket and sexy crop top. The casual outfit doesn’t quite scream murderess, but it’s still pretty cute.
Lace Button Front Bra Top, $34
Classic Bomber Jacket, $59.99
Her edgy goth style in Beetlejuice
Raise your hand if you ever aspired to dress like goth chic Lydia Deetz in Beetlejuice (1988). Besides her red bridal dress, you’ll likely see precocious Lydia sport all black to express her morose soul. We’re loving the moody outfit she dons when she spots the Maitland ghouls from outside of her new home. Here, she has on her signature wide-brim black hat and flowy dress. It’s a great style to wear when you’re feeling like flaunting something both edgy and vintage.
Black Big-Brim Hat, $35
Fit & Flare Shirtdress, $145
Her carefree, summer look in How to Make an American Quilt
In How to Make an American Quilt (1995), Winona plays Finn, a grad student who goes back home one summer to finish her thesis and sort out her feelings about her fiancé. Finn’s casual attire reflects her carefree spirit. She effortlessly wears grungy ’90s looks throughout the film, including this outfit that consists of a checkered dress shirt over a pair of overalls.
Ultimate Plaid Boyfriend Shirt, $32.99
Denim Shortall Overall, $49
Her badass mom outfit in Stranger Things
We’d be remiss not to include Winona’s role as the brave and persevering Joyce Byers from Stranger Things, which technically isn’t a movie, but still a major highlight in her career. Joyce isn’t usually dressed up to the nines, but her simple outfits can still be very stylish. Here, she’s investigating Terry Ives’s case with Jim Hopper while wearing a sleek, black moto jacket over a slouchy turtleneck sweater.
Black Leather Look Waisted Jacket, $72
Red Tannin Oversized Turtleneck Tunic Sweater, $69
The dancing it out with mom outfit in Mermaids
Winona earned a Golden Globe nomination for Mermaids (1990) as Charlotte, a guileless and quirky teenager who finds herself at odds with her flighty mother, who’s played by none other than Cher. One of the movie’s best scenes shows the entire family dancing it out in the kitchen. Charlotte enjoys this fleeting moment of cheer with bright red pants and a fun print blouse.
Banned Retro Reminder Button-Up Top in Red Floral, $45
High-Rise Super Skinny Ankle Pants, $25
Whether you’re feeling fun and summery or dark and edgy, there’s a timeless Winona look for you.
