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Clueless Turns 17! The Movie's Fashion Legacy Plus a List of 8 More '90s Fashion Gems To Add to Your Netflix Queue

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You know Frank—he's been writing about menswear, sales, television, new shops, the recession, Lisa Loeb, the Golden Girls and getting blasted for Racked for over two years. Well, we think it's time you got to know him and his quirky-irreverent views on life and fashion even better with his column: Love, Frank. Taking the form of an open letter and always signed with love, Frank will rant about whatever style-related conundrum he encounters in a given week. So buckle your two-toned leather Moschino belts, folks, it's going to be ? Something.

A major moment, via the Jane Austen Film Club

Dear Fans of Frivolous Movies and Seekers of Unlikely Fashion Inspiration,

I'm not implying that Clueless is frivolous (it's so not) or that it's an unlikely place to seek out bits of fashion inspiration, because, well, Clueless is a straight-up fashion movie. But, it is a good jumping off point; and it's especially relevant right now for two reasons. One, the movie just turned 17—it came out in late July of 1995. That makes the movie about as old as the characters within it, which is kind of a fun, meta thing to think about. It also makes each and every one of us (who, you know, can quote the whole thing verbatim and remember exactly when it came out and bought the soundtrack and wanted to live it) feel, well, really old.

And two, the costuming within Clueless just looks really fresh right now (I just watched my brand new Walmart DVD). All that Jill Stuart school-girl plaid, all the slinky body-conscious Calvin Klein, all the leather and the layers and the '90s street looks as distilled and refined by the Hollywood and fashion machines. It all looks more now than it looked then, and it looked pretty damn now then too.

And, well, it was incredibly inspiring. My fall is going to be all about tartans, I've decided. But more than that, it has me looking at all my DVD's more closely—for fashion inspiration. And fortunately for my new screen-scrutinizing hobby, summer means lazy beach vacation means no cable means piles and piles of DVDs. Here are some favorites—note that these choices pertain directly to the Clueless Generation and should be readily available on Netflix or in the $6 close-out bins at your local big box retailer and/or used on Amazon for approximately 85 cents plus shipping.

Jawbreaker: Granted, Jawbreaker (1999) is a pretty wretched movie—its current rating on Rotten Tomatoes is a 7. But, it's dark and stylish and has a few pretty hilarious moments. It also features this totally bizarro retro, pin-up girl version of high school in which girls wear exceedingly slutty twinsets in bloodier shades of red than their teeny tiny wool skirts; as accessorized by patent clutch bags (who carries books?) and plexi-framed '50s sunglasses. You'll also meet nerd girls in hooker-length pleated skirts, booties, and socks—very Williamsburg; and drama club hetero-heartthrobs whose looks fall somewhere between Kurt Cobain and James Dean. Bonus: The Donnas perform at the prom and all those Imperial Teen songs! 

Romy and Michele's High School Reunion (1997): While we're on the subject of Jawbreaker's whole retro bombshell aesthetic, we might as well just mention Romy and Michele. Their '90s retro-fetishism is a more candy-coated iteration of the decades-spanning nostalgia trip I absolutely love in Jawbreaker (and, frankly, consumed throughout the whole decade—think Pulp Fiction, the Brady Bunch Movie, Matthew Sweet, Gwen Stefani, The Wedding Singer, That '70s Show, the boys on 90210, that alternative compilation of School House Rock covers). But more than the vintage cuts and jaunty prints and SoCal vibes, I love that the two always dressed in tandem. The silhouettes and lengths of everything they wear is always perfectly attuned. Their colors always match. They look great in that convertible Jaguar. And, omigod, who doesn't want to play in the boutique they end up opening at the end? I mean, lemon-print dresses! 

Reality Bites (1993): Another movie that looks more backward than forward—note everyone's (inexplicably perfectly fitting) thrift-shop clothes, plus Vicki's crazy kitsch collection—the costuming in Reality Bites actually looks authentic. Real people dressed (and dress) like this. It's a snapshot of struggling post-college hipsters (though this was decidedly pre-hipster, so Gen X-er? Alt-person?) meandering through their underpaid lives. In terms of styling, it's all about Winona Ryder's Lelaina Pierce and her era-defining look. I defy you to find a more perfect-looking and utterly sexy example of thrift-chic androgyny. She makes a pocket tee and a pair of 501s look Celine-exquisite. Her vintage shirt dresses are perfection. Those round-framed sunglasses are the holy grail.

Heathers (1988): Speaking of Winona Ryder, you must revisit Heathers. Though not technically '90s, it is brilliant and funny and so dark and crazy and out there that you almost can't help having one of those WTF, how-did-this-movie-get-made moments. But it just oozes style. Note that each of the Heathers, and Veronica, is consistently wardrobed in complementing monochromatic looks that symbolize said character's traits. Also note that as the movie progresses and people really start biting the dust the characters start wearing each other's colors or going black and white. It's a really fun progression. And, also, look at the wallpapers. They're awesome.

Empire Records (1995): It's tough to admit it, but revisiting this movie reveals that it is, in fact, kind of a dud. Not in a Jawbreaker so-terrible-it's-nearly-brilliant kind of way. More of, well, just a dud. You can, however, revel in the soundtrack—which is as hip as mainstream gets and has a totally fun, nostalgic vibe. You can also admit that the reason any of us has ever bought a mohair and/or angora sweater is absolutely because of Liv Tyler in this movie—even if that electric sky blue color is so Banana Republic Stretch on clearance circa 2001.

Splendor (1999): Have you seen this movie? You should. It's bizarre and charming and so of-its-era. But mostly I love that main character Veronica—this beautiful, porcelain person with a little snub nose and a slew of adorable vaguely retro mini-dresses—styles her hair differently like every day. So refreshing! Why don't girls do that in real life? Hair-inspiration! Also, you can't not love her artist buddy for being a hilarious walking stereotype and a cameo of late-'90s lifestyle beverage Orbitz (the clear stuff with the floating atomic blobs).

The Last Days of Disco (1998): One of the chicest, most cohesive-looking movies I can think of—not to mention chatty and charming and laugh-out-loud funny. Peep what in-the-know New Yorkers who didn't totally know that disco was just about over wore to those fabulous clubs. And to work the next day. And it's not just the clothes—it's the spaces, the decor, the scenery. That perfectly WASPy first apartment split between three privileged publishing girls. All those restaurant scenes. Even the office spaces. It's all there for a reason and all that is a hallmark of filmmaker Whit Stillman's sensibility. Go back further to his 1990 film Metropolitan to see perfect, tried-and-true American preppism in all its timeless, trend-less glory. Before the fashion set tweaked the proportions, amplified the branding, sourced from Japan, and created fetishistic Americana at a mall near you.

Cry-Baby (1990) (also Hairspray, 1988, and Serial Mom, 1994): While I'm on directors who create stylish, visual worlds, I must mention John Waters. And, frankly, these are—without a doubt—Waters' most accessible, enjoyable movies. Further, each is just a delight for the eyes—whether period pieces that portray the '60s with joy and accuracy and just the right cast of sweet, frivolous camp (the former two); or contemporary pieces with a retro-kitsch aesthetic (Serial Mom); they're a sensory feast. Great clothes, great sets, great fun—and always just over-the-top ridiculous. Plus, Ricki Lake.

So, my two cents. Love them? Hate them? Did I miss any classics? Let me know in the comments—I'm always down for some fresh inspiration.

· Love, Frank [Racked]