Throwback Snaps Of Winona Ryder Will Give You All The Moody Fashion Inspo You Need

It's hard to think of '90s fashion without Winona Ryder coming to mind. Although she first came to fame in the late '80s thanks to the films "Beetlejuice" and "Heathers," it wasn't until the dawn of the 1990s that she solidified herself as a style icon — and a moody one at that. With her iconic pixie cut and penchant for black clothing, Ryder serves as the perfect inspiration for the new wave of nostalgic fashion. From the '90s dress trends that were hot in 2025, to the reemergence of butterfly clips, the decade's distinctive style is once again all the rage.

"It's hard to talk about the influence of the '90s because I lived through it, so I see it differently than the younger generation," Ryder told Harper's Bazaar UK in March 2018. "People are obviously carefully cherry picking the better trends — there were a lot of bad looks in the '90s." While that's very true, a quick jaunt down memory lane proves that Ryder never fell into the trap of silly trends and what she calls "bad looks." Considering the way she always embraced her own unique style, that's probably how the actor was able to avoid the cringe-worthy pieces of that decade.

As one of the celebrities whose eye makeup never left the '90s, you could say that Ryder is the patron saint of the decade when it comes to fashion and beauty. If ever there were someone to inspire a moody look, Ryder is it. She never failed to deliver on that end.

In the 1990s, black boots were a staple. Whether they were black combat boots, platform boots, or knee-high boots, the versatile shoes were paired with both short and long floral dresses, skirts, jeans — pretty much anything, really. In this photo, three '90s icons — Winona Ryder, Liz Phair, and Rosanna Arquette — demonstrate a few ways to style black boots. All of the looks deliver major moody vibes, but it's Ryder's, in particular, that truly embodies the fashion of the decade. The long dress with black boots combo exhibits femininity with a dash of toughness.

If you want to rock one of the '90s minimalism looks that are making a comeback, then overalls are the way to go. Not only are they comfortable, but they can easily be dressed up or down, depending on your mood or the event. In 1993, Winona Ryder attended the MTV Video Music Awards alongside then-boyfriend, Dave Pirner, of the band Soul Asylum, wearing overalls with a button-down shirt and Chuck Taylor sneakers. The best part about investing in overalls, if you don't already have a pair, is that they never really go out of style.

Although red lipstick has been a staple in just about every era, the look got a new spin in the 1990s, when deep wine red was in high demand. The shade was everywhere, even extending to nails, like Channel's iconic nail polish color, Vamp. Ryder, as always, was on top of the moody trend. The "Reality Bites" star often appeared at events in head-to-toe black — a look she almost always paired with a bold shade of dark red lipstick. Bringing the perfect hint of color, a burgundy lip is an easy way to elevate an ensemble, while keeping the sultry mood in place.

As if Winona Ryder's choice of roles weren't already dark, in 1992 she starred alongside Gary Oldman and Keanu Reeves in "Bram Stoker's Dracula." When she attended the LA premiere of the film, she skipped the black, opting for a royal blue corseted suit set with white lace at the hem and along the neckline. Although the only black she wore that night was in her heels, there's still a lot of moodiness in her look, and it was a very appropriate ode to her character, Elisabeta.

In 2000, while growing out her iconic pixie cut, Winona Ryder attended an InStyle event rocking jeans and a Jackson Browne T-shirt, with a blazer and (now back in fashion) Y2K skinny scarf in hand. The look was simple, yet stylish, and is one of Ryder's go-tos. When Harper's Bazaar UK asked the actor in March 2018 about her wardrobe essentials, she said, "Everyone's different, but socks and underwear, a comfortable pair of jeans, favorite T-shirt, and a soft sweater. But that's just me. I don't think I'm qualified to tell others what theirs are." Though Ryder isn't prepared to prescribe the look to everyone, we feel confident saying jeans and a T-shirt are never out of style.

At the height of paparazzi mayhem in the late 1990s and early 2000s, photos were constantly being snapped of celebrities out and about — so much so that LAX started to feel like another red carpet event. But here's the thing: You don't need to be the always-stylish Winona Ryder to use the airport as an excuse to try out a new look and let your moody fashion shine. A one-color look, from head-to-toe, complemented with a denim jacket, shoulder bag, and sunglasses, and you're looking effortlessly chic while catching your flight. 

Even if your plans for the day are dedicated to bed rotting as a means of self care, that doesn't mean you can't be stylish. After all, we dress for ourselves and not for anyone else (although an audience does make it a bit more fun). In the mid-1990s, Winona Ryder posed for a series of photos in her New York City apartment, cuddled up in bed in matching flannel pajamas. While it's not her normal black, Ryder still manages to exude moody style in blue stripes, with her messy hair and doe-eyed look.

If you thought you have to skip glitz and shimmer to pull off a goth-y look, think again. In 1997, Winona Ryder attended the 69th Academy Awards wearing this stunning art deco-inspired black dress with sequins and beading that provided just the right amount of sparkle. True to Ryder's style, she completed the look with black heels, a black handbag, her dark pixie cut slicked back. The only pop of color is the actor's red lipstick, so she's basically ready to hit up a séance on the way home. 

Nothing says moody girl fashion inspo like this photo of Winona Ryder from the mid-1990s sitting at home in a sleeveless T-shirt, backwards baseball cap, and guitar in hand. Given that the '90s were the era of grunge music, this look — including the guitar — is spot on for the decade. Of course, Ryder is no poser, and in her 1999 film "Girl Interrupted," the actor played an acoustic guitar, so we know she can play at least a few chords. Looking like she's about to bust out a Nirvana song, Ryder nails the moody, indie grunge style that was so popular in the '90s.