• Wed, Jan 8 - 11:20 am ET

5 Great Fashion Looks From Terrible 90s Movies

Image: TriStar Pictures

Image: TriStar Pictures

I like to think that most of fashion from the 90s was worn by the general population as some bizarre collective joke for future generations to look back upon. Alas, even in a sea of floral jumpers and butterfly clips, there have been some looks that I could see making their way into the twenty-teens. (What do you call this decade, anyway?). Where have I collected some of my favorite 90s looks? Oddly enough, from some of the movies that hold up the least. Okay, so the plot may be convoluted and the dialogue may be sub-par, but admit it: You know you love these cheese-fests regardless. And let’s take a look at some of the looks that I also love from them:

Drive Me Crazy (1999)

When this film came out, I was a child with a passion for Britney Spears and parents who refused to take me to see this PG-13 nightmare of a movie. In case you aren’t familiar, the plot follows Melissa Joan Hart and Adrian Grenier as neighbors from different social circles who team up to make their exes jealous, even though both of them think that they’re slummin’ it by fake-dating the other. In the end, the two fall in love for real, and adorable things like this happen:

Honestly, I think that all of the outfits worn by Melissa Joan Hart in this movie are horrible. It’s all spaghetti strap tanks (which I was NEVER allowed to wear in school, lest girl’s exposed shoulders cause a riot) and too tight cardigans and I am not about that life. (Though, for the record, I was totally about that life in the 90s). Adrian Grenier’s character, while adorable, did not do much for me in the style department, either. Who did? This minor character — played by Ali Larter, but not looking anything like the Ali Larter we know today — named “Dulcie.” Here she is:

Photo: 20th Century Fox

Photo: 20th Century Fox

I don’t know why, but I’m totally about what Dulcie is doing. Her hair is an awesome color and it matches her lipstick, which is an edgy-yet-somehow-still-understated shade of burgundy. Maybe I wouldn’t rock this look year-round, but with the right amount of hair chalk, this look could be mine for like… two days.

She’s All That (1999)

I know, I know, She’s All That is a modern day classic, but let’s all agree that it isn’t exactly Oscar-worthy, okay? This take on the Pygmalion story has all of the things that you need for a great 90s teen romance: the star of the football team, an art geek, and adults playing teenagers. Another thing we need to agree on? That Rachael Leigh Cook was perfectly adorable in her glasses and overalls. Yes, she did wear some amazing footwear descending the staircase to the sweet sounds of “Kiss Me” by the Sixpence None the Richer, but I still have great admiration for her original look.

That red dress was classic, sure, but tell me that this low-key outfit and messy bun doesn’t scream casual chic.

Photo: Miramax Films

Photo: Miramax Films

I love everything about this. Who needs a major Cinderella moment when you have such taste? Clearly, her look would be much more appreciated after high school at whatever fancy art school she got into.

Cruel Intentions (1999)

Oh, Cruel Intentions. I’d love to say that I hate-watch this movie but that would be a lie, because I enjoy every single moment of this incredibly risque teen romance. Who would have thought that a modernization of a French novel would make such a great Sarah Michelle Gellar vehicle? Or that a kind of incest-y plot point would be just the thing to engage teen audiences! (This bodes well for Lifetime’s Flowers In The Attic TV movie). Like She’s All That, this is yet another movie about teenagers betting on very real people’s lives. This time it’s not about turning a girl into a prom queen as much as it is about destroying her reputation and tricking her into losing her virginity to a sociopath. Because teenagers love to bet on stuff? I don’t really know.

At the center of this bet was Sarah Michelle Gellar’s Very Evil Stepsister, Kathryn. Kathryn did a lot of horrible things to a lot of people (most of whom were equally as horrible) but one thing that she did absolutely right was dress herself. While I did not want to be as evil as Kathryn, I did want to wear all black in the middle of summer and have perfectly tailored skirts and look terrifying in the chicest way.

I mean, just… flawless.

I definitely blame Cruel Intentions for my persistent obsession with Gossip Girl. (Yes, I know it’s over, I just can’t let it go…)

 Jawbreaker (1999)
Jawbreaker was the 90s answer to Heathers, which has a-plenty of delightful fashions to choose from. Except while Heathers remains brilliant and darkly funny, Jawbreaker is neither of those things. This satirical (I think? I hope?) film about a group of popular plastic-types who accidentally kill the nicest member of their pack during a birthday prank gone wrong is filled with neon clothing and lots of clothes that your parents would not let you out of the house in when you were sixteen. It’s a pretty fun ride. 
Jawbreaker
via
 If I loved Cruel Intentions’ Kathryn for her penchant for black, then I loved Jawbreaker’s characters for their color-worship. I never really experiment with bold colors, so this film is pretty inspiring. I particular love everything that Rose McGowan’s character wears, because when will I wear a head-to-toe purple outfit WITH a matching neck scarf? I will never do that. But, like, because of Jawbreaker, maybe I kind of want to try?
Image: TriStar Pictures

Image: TriStar Pictures

Great Expectations (1998)

Image: Art Linson Productions

Image: Art Linson Productions

UGH THIS MOVIE. I LOVE IT.  While not necessarily regarded as terrible 90s movie, it never received the accolades that it clearly wanted to. There’s a lot of symbolism in this film, but the most obvious is the director’s use of the color green. Green is everywhere in this movie — it represents money and rebirth and also really brings out Gwyneth Paltrow‘s light features.

Image: Arts Linson Productions

Image: Arts Linson Productions

When I saw this in freshman English, I remember specifically shopping for this lush shade of green, and I’m still partial to it today. Another major inspiration from Great Expectations? The elegant, beautiful, weird-as-hell things worn by Ms. Dinsmoor, the eccentric Ms. Havisham character, played by Anne Bancroft.

Image: Art Linson Productions

Image: Art Linson Productions

Long strings of pearls and kimonos? Sign me up, please.

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  • CMJ

    Weirdly enough, I always wanted that coat Ryan Philippe wore in the last scenes.

  • elle

    I still want to dress like SMG in Cruel Intentions (i also love watch that movietoo)….

  • Lindsey Conklin

    I kinda like all of these admittedly horrible movies…haha

    • Kaitlin Reilly

      Me too! Especially Cruel Intentions/Great Expectations.

  • Anne Marie Hawkins

    I think that last pic might actually be a caftan? I don’t know, but the pearls are basically their own top.

  • Joanna Rafael
    • Kaitlin Reilly

      I hate to admit how much I love this movie… Rose McGowan is so good at crazy. Love her dress.

    • Joanna Rafael

      It’s the only movie I have ever purchased on itunes like a weirdo.

  • Julia Sonenshein

    So much style inspiration right here.