7 Reasons Why Winona Ryder Is The Ultimate '90s Dream Girl

It’s a big week for Winona Ryder. On top of ruling the press circuit in support of her upcoming HBO miniseries, Show Me A Hero, the industry veteran/person we’re still aspiring to be, confirmed to Seth Meyers that a Beetlejuice sequel is in the works. (Pause for screams of joy and saying “Beetlejuice” three times.)

So yes, everything’s coming up Winona. But on top of HBO, the upcoming full-length Experimenter, and the recently-announced Netflix show, Montauk (in which Ryder will star), the actress will also be celebrating the 25th anniversary of Edward Scissorhands in December. Which ignited a discussion on why and how we crowned Winona Ryder as the official nineties posterchild. Better yet, why we still aspire to be her most famous characters, twenty-plus years after we first met them.
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Photo: Ron Gallela/Getty.
1. Her sense of style

Tim Burton's costume department aside, we can all agree that Winona Ryder epitomized the laissez-faire, vintage-inspired vibe of the decade. At the top of the nineties, we saw her in pieces like faded jeans and leather jackets (effectively epitomizing the badassery many of us still hope to evoke), while her characters — specifically Lelaina in Reality Bites — opted for suburban androgyny like short-sleeve dress shirts, tank tops, and loose denim. (A look we saw echoed by Ryder herself in oversize blazers during the later Depp years.)

But what’s continued to endure us to Winona’s nineties style was her willingness to try anything. The nineties was a decade that introduced style experimentation on a greater scale (see: the influence of street style via designers like Marc Jacobs and Alexander McQueen), and saw an overt combination of old and used clothing with high-end finds. Like designers themselves, Ryder never shied away from taking risks. So, considering the nineties were defined by risk-taking, snap judgements, and a complete abandonment of eighties excess, only someone willing to navigate trends without regret could uphold the spirit of the decade.
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Photo: Joe McNally/Getty.
2. Embodiment of minimalist beauty

Perhaps one of the greatest feats of the nineties was its ability to dismiss the large-and-in-charge nature of eighties beauty standards. While the turn of the decade still saw its fair share of hairspray (see: young Winona, circa 1991), the years gave way to natural waves, straight hair, and, in the case of Ryder, a loss of length completely.

Like fashion, beauty in the nineties also began paying homage to androgyny, as short hair was no longer teased to excess, or permed, or primped. Instead, women like Winona embodied the abandonment of conventional femininity by cutting their hair and just letting it be. This is why we still care that in 1994, Ryder debuted a shorter, wavy haircut that reflected the minimalism popularized by the likes of it-girls Kate Moss of Chloë Sevigny. In an act of rebellion (or what seemed like it — especially to those of us too young to begin challenging things), Winona proved that she wouldn’t be defined by hair length or the product in it. Like the rest of her generation, she didn’t need permission to change or to grow.
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Photo: BEImages.
3. Her relationship with Johnny Depp

Granted, as adults who’ve read more than enough pieces on the relationship between Johnny Depp, Winona Ryder, his “Winona Forever” tattoo (RIP), and the Kate Moss aftermath to write books of our own. (Or just read Champagne Supernovas by Maureen Callahan.) But in the nineties, the couple helped kick off the era of celebrity tabloid journalism we’re still in.

Having met at the Great Balls of Fire! premiere in 1989, Ryder and Depp embarked on the infamous romance that saw them engaged by 1990 — and not together three years later. Arguably, the couple’s intensity ran parallel to the decade’s penchant for sensationalism, as reporters, paparazzi, and the public were left to fill in the blanks by reading into body language, quotes, etc. It marked the beginning of what’s come to define almost any coupling between famous people. That, and the beginning of any/all tattoos that say “Wino.”
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Photo: Moviestore Collection/REX USA.
4. Intellectual and emotionally-fulfilling film roles

If there’s one word to describe Winona Ryder’s film career, it’s “interesting.” Especially since the nineties saw her play a range of characters that were equal parts complicated (Lelaina), tragic (The Crucible), damaged (Girl, Interrupted), and engaging (Little Women). At no point did Ryder place herself in a box or typecast herself as a specific type of character. In fact, despite being so aligned with the nineties, only her turn in Reality Bites really qualifies Winona as being the fictional voice of a generation. Instead, she embodied her generation in a much more valuable way.

Considering the nineties (and most specifically, Generation X) were built on challenging the conventions of earlier generations, few things embody that call to rebel like accepting a fleet of unique film roles. Winona Ryder built a career on variety, in a decade that valued it supremely.
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Photo: Moviestore Collection/REX/REX USA.
5. Representation of counter-culture

Of course, it’s not like we’re about to take Winona’s role as Lelaina in Reality Bites lightly — because that movie specifically tackles the Gen X idea of doing what one wants, versus doing what one’s expected to do.

Here’s why this matters: Lelaina graduates university at the top of her class, and because of that, is expected to hold down a job and slide into the workforce despite her dislike of her current job. She wants to be a filmmaker (and/or documentarian). And eventually, she’s either forced to compromise her vision for her first documentary series (a.k.a. her dream) or start from the bottom in a different way. (With a love triangle thrown in for good measure.) To be honest, it’s as true a tale now as it was then, especially with lines like “Honey, the only thing you have to be at 23 is yourself.”

You can’t help but wonder if series like HBO’s Girls would even exist without it.
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Photo: Jim Smeal/Getty.
6. Punk rock credibility

Sure, we can chalk up Winona’s punk rock credibility to Johnny Depp (never forget The Viper Room), Tim Burton (the spokesman of pop-goth), or her black hair and leather jacket. Or, we could acknowledge that Ryder’s punk rock self as a picked-on teen.

As a woman whose identity fell in-step with the subculture’s rejection of norms and embracement of rebellion, Ryder had first-hand experience with being on the outside looking in. In a 2013 interview with V, the actress opened up about being on the receiving end of a homophobic attack back in school, all because she’d been obsessed with Bugsy Malone and had cut her hair short. As a result, she started homeschooling, which led to her career as an actress. Winona Ryder is a survivor and always has been.
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Photo: Matt Baron/BE Images/REX USA.
7. Genuine and unpolished

Living as a normal human being is scary. But to live so publicly and honestly in the shiny, new spotlight of nineties-bred celebrity culture is something we can only describe as terrifying. However, Winona established herself as a genuine, unpolished presence despite this. This is thanks in part to sharing that she’d been a “full virgin” when she’d met Johnny Depp, and/or that he’ll “always be in [her] heart.”

This was in stark contrast to the glam-infused eighties, or overly polished fifties, and seventies. Representing her generation appropriately, Winona offered a breath of fresh air to the stuffy-seeming world of famous people. She proved — via her outspokenness, style, and candidness — that stars were just like us. Or maybe more accurately, that stars are just people. And people are more complex than just being stars.
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