In Hollywood some people age like fine wine and others like milk; Winona Ryder is part of the first group. As her career has progressed from 90s poster girl to 21st century Netflix queen, so has her style. As we’re researching our looks for Stranger Things Secret Cinema later this year, we came across a plethora of absolutely killer Winona looks that we are desperate to recreate. So in honour of this icon we run down the top Winona Ryder Fashion Moments of all time.

Best Winona Ryder Looks

1. Slacks ‘n’ sex appeal

Winona in a suit

Winona’s style in the 90s played with androgyny, as she carved out her iconic style in over-sized blazers, shirts and chunky shoes. This shoot perfectly encapsulates her style, with a crisp shirt, braces and smart slacks in a totally sexy, laid-back ‘morning-after’ look. We’re putting a twist on this look by pairing our favourite high-waist black trousers with an over-sized vintage shirt worn over a black bralet. Perfect summer-weekend attire.


2. Biker Babe

Johnny Depp e Winona Ryder, 1990

One of the most iconic and beautiful celebrity couples to have ever existed, Depp and Ryder were the IT couple of their time. Winona wore this look to a Vogue party in 1990, looking fresh faced  alongside Johnny Depp. We’ve bookmarked this classic look for drizzly, autumnal nights out when you are desperate to wear your favourite party dress, but don’t want to be caught in the cold. Grab a fitted, flirty, mini dress and an over-sized, vintage leather jacket for the ultimate effortless, cool-girl look.

3. Veronica (Heathers)

Winona Ryder in Heathers

A cult classic and a story that went on to inspire other 90s cult favourite such as Jawbreaker, Heathers is an iconic piece of film history, as were the costumes. It’s preppy-ness overload from start to finish, and always has us reaching for our pleated skirts whenever we watch it. Winona’s look is so simple yet instantly recognizable, as the powder-blue, puffball skirt contrasts with the wickedness of Christian Slater’s character JD. We’re recreating this quintessentially 80s look, pairing a blue mini skirt, black vintage crop top and blue cardigan - who knew this costume would be so wearable?

4. Kim Boggs (Edward Scissorhands)

ZOE on Instagram: “Winona Ryder in Edward Scissorhands (1990)”

One of Winona’s most notorious roles was sweet Kim Boggs in Edward Scissorhand; is it just a coincidence that Ryder’s CV happens to be all of the biggest. Cult classics to date? With blonde hair and a pastel wardrobe, she looks heaven-sent. The perfect low-key look to recreate for an easy Halloween costume or a fun formal look, you can put together this outfit with a white, skater dress and the perfect peachy makeup.

5. Eternally Effortless 1991

From Heathers to Stranger Things: Winona Ryder's best looks

Finally an excuse to wear your favourite, comfy outfit - you’re actually channeling 90s Winona, OBVS. This kind of look is the perfect Friday outfit as it will take you from office to pub to bar, and even to Saturday brunch if you feel like going all out. Nail effortless dressing with your best pair of vintage Levi’s, classic band tee and leather jacket. The beauty of this look is that with a simple change of shoes you can completely change it up.

6. Joyce Byers (Stranger Things)

Winona Ryder in Stranger Things | ASOS Style Feed|HAIR!!

In 2016 Winona took our screens by storm again, this time in one of the biggest, most-talked-about and most-memed shows of the decade. We are head-over-heels obsessed with all of the looks in the past three series of the show, mining our huge vintage collection to find the perfect 70s and 80s pieces to build our own Hawkins look. Joyce Byers, the most stressed-out mum in TV history has taken Ryder’s look in a different direction. The classic Joyce that both the viewers and Hopper fell in love with is a cardigan-wearing, khaki-loving mum-style icon. Throw on your best corduroy trousers, flannel shirts and striped tees and you’re Upside-Down ready. 

For more outfit ideas for the upcoming Stranger Things Secret Cinema then head over to our blog where we show you how to put together the ultimate Stranger Things- inspired look. Alternatively you can shop our Stranger Things edit or our 90’s era vintage.

Words Eloise Gendry

August 08, 2019 — Eloise Gendry
Tags: Culture