Top 5 Favorite Outfits Women Have Worn in Movies

Welcome to Top 5 Fun Friday, a regularly-occurring blog feature where I give you a list of extremely specific pointless shit from my life no one asked for. Why? Because the internet is STILL incredibly un-fun in 2021 and I enjoy blogging. It’s Friday and these will be fun! This week’s list…

Top 5 Favorite Outfits Women Have Worn in Movies

The Thomas Crown Affair: The Wardrobe | Feather Factor
Just off the podium, but I decided on a different outfit from the same movie.

Back in college one of our crew’s favorite movies was SLC Punk. It still is, but for the point I’m about to make, let’s put ourselves back in college. At some point during the seemingly limitless amount of time you could devote to hanging out with your friends, I asked my friend Keith if he thought of himself as one character from the movie, who would it be? He answered Heroin Bob because like Bob, Keith was pretty high strung, hated drugs, hated needles, and was way more hardcore than he looked.

I asked who he thought I was, and he answered “Eddie.” For those of you who don’t remember, Eddie was into women. He had spiked blond hair and kept a cigarette behind his ear, two affectations I also shared. To hear Stevo’s voiceover in the film, Eddie didn’t love women in a gross, pervy way, and I bring this up because that’s the tone I want to set for this blog. I love women, too, and I hope very little of what comes next comes across as pervy, leering, or otherwise too uncouth.

While I’m in no way trained or skilled in fashion technically, my wife can tell you that I’ve got a pretty good eye for it. I have a good sense of color, contrast, and lines. Kristin will ask me about an outfit she’s questioning, and I’ll give her honest feedback that more often than not she takes. Don’t get me wrong, the women on this list are all pretty much impossibly gorgeous and that’s not insignificant in my motivations here, but this is also a tribute to rewatching movies and getting something new out of them each time. More and more I appreciate things like set design, score, and, germane to today, costuming.

Plus, women’s fashion is just infinitely more interesting than men’s fashion, so let’s appreciate some awesome women’s clothes from movies I like. Strike a pose and haul your asses down the runway, ladies.

Emily Blunt in The Devil Wears Prada

Men are fucking stupid. I know this because I am one, and I am fucking stupid. Exhibit A: When this movie came out in 2006 and then was subsequently broadcast around the clock on cable ever since, it took me until hearing Paul Rudd say he loved in in the movie I Love You, Man in 2009 to hear a dude admit that he liked this movie. And when Paul Rudd said it, it was a punchline! And he was fictional!

No, this movie fucking rules and I’m sad it took me like a decade to realize it. John Krasinski refers to it as “the kryptonite for channel surfing,” and he’s absolutely right. It’s devastatingly funny, it’s got a multitude of satisfying character arcs, and the fashion is, as one would hope for a movie like this, absolutely on-point and ridiculously fun to look at. I could pick any of a hundred outfits from this movie for this post, but instead let’s pay tribute to probably its most underrated character.

Emily Blunt absolutely steals the show in every scene she’s in. She’s ambitious, but not terribly savvy, which is a posture rich for comedy. After getting complimented on how she looks before the Met Ball, she says, “Thank you! I’m one major stomach flu away from my goal weight,” a line so breathtakingly cutting about our cultural dialog around body image, it makes me laugh every single time. She’s naturally hilarious and thoroughly captivating to watch, which is probably why she’s able to make Dwayne “The Rock” Johnson laugh so goddamn hard.

Her outfit seen here early in the runtime sets the tone for the rest of the movie because Emily wears it as the audience preps for Miranda’s first appearance. She looks tough and severe and chic in her black on black on black (all in slightly different shades), but look a little closer, and those fabrics are all soft. She is but another Nerf ball for Miranda to toss about as she sees fit, the softness of which belies not only her role within this organization, but reinforces that she probably just needs a hug.

Keira Knightley in the “To Me You Are Perfect” Scene from Love Actually

This scene has been parodied to death, and watching it sometimes feels like pure torture for its treacly sentimentality and blunt force romanticism. But hot damn, Keira Knightley! I mean, I totally get why Andrew Lincoln (pre-Zombies and pre-pronouncing the name “Carl” like the word coral) would be hopelessly hung up on her.

That sweater doesn’t seem like it’ll be terribly useful weather-wise in London in December, but Knightley certainly wears the shit out of it. The white connotes the angelic esteem Lincoln holds her in, and Knightley’s soft babyface features (she was only 17 when she filmed this, which, ok, now I do feel a bit icky) elevates that feeling. I don’t recall seeing a sweater in that particular cut before or since. It accentuates Knightley’s athletic but feminine shape, further helped by the low-rise jeans giving way to a small peek of midriff.

It’s at this point that I remind everyone I turn 40 in a few days, and thus am about to formally age out of the cultural demographic anyone truly gives a shit about. With that in mind, I still think teenagers and people in their 20s today wear their pants so goddamn high, they all look like fucking Urkel.

I know I’m old when much of the music and fashion of today makes no sense to me, and I know that’s ultimately a good thing. You have to tear down the iconography of prior generations in order to construct an image for your own. It’s not like they need my permission or even my endorsement to do so, or like I could stop it even if I wanted to, so proceed, you young punks.

But seriously, the high-waisted pants make these kids look like such dweebs. I’m already ready for the pendulum to swing back in the other direction to a more acceptable belt line. And Keira Knightley’s appearance in this movie is Exhibit A for why the lower cut jeans rule.

Alicia Silverstone in the tardies scene in Clueless

Hey, speaking of young people! The hippest movie of 1995 still holds up remarkably well, and a huge reason why is because Alicia Silverstone’s portrayal of Cher Horowitz is beautifully nuanced. Yes, she’s shallow and superficial and consumed with the trappings of consumerism, but Cher also works hard, stands up for herself, and is deceptively smart. Like all great movies, it functions on more than one level simultaneously, excelling at both. It’s both satire and escapist, a nifty trick for a frothy teen comedy.

Cher’s signature outfit from Clueless is either that plaid yellow skirt suit she wears at the beginning of the movie with the long white socks (which Silverstone amusingly parodied with her son on TikTok), or the red cocktail dress she wears while watching “Sparatacus” with Christian, which are both iconic looks. But for my money, her best outfit in the movie is this number.  It’s an elegant and undeniably feminine take on a powered up business suit.

The chalk stripe blazer with the stark white shirt cuffed and rolled up mean she’s ready to negotiate with Mr. Hall over how many times she was tardy while also teeing him up to further his courtship of Miss Geist. The accessories, the rounded beads of her necklace and earrings along with the fuzzy pen topper provide a nice shape contrast to the hard lines of the blazer and shirt. The beret looks nice enough and Cher wears it well, but it mostly just reminds me that berets were really a thing in the 90s for reasons I’ll never know, and that they’re probably the goofiest pieces of headwear ever invented.

Rene Russo breaking into Thomas Crown’s house in The Thomas Crown Affair

Many of my favorite movies are ones that feature movie stars doing cool movie star shit. The Thomas Crown Affair features Pierce Brosnan being more effortlessly cool than at any point during his run as James Bond, and Rene Russo in her prime as his worthy adversary. Give me high stakes heists! Give me ballroom dancing with witty repartee! Give me lots of deliciously chewy plot twists! Give me discussions about art, artists and paintings I know nothing about! And give me Rene Russo absolutely owning the screen in everything from ballgowns to her birthday suit!

You could pick any number of outfits Rene Russo wears in The Thomas Crown Affair because she looks like a million bucks in all of them. While doing some light research for this piece, I learned that apparently most of these outfits are the work of Michael Kors, who, one commenter noted, was “riding high on the luxurious minimalism (rich fabrics, simple lines, a flourish of detail) of the late 1990’s.” That’s incredibly well-observed, and I suppose could be applied to Cher Horowitz’s general sense of style above as well.

My personal favorite is the leather number she wears when she breaks into Crown’s house and finds the decoy painting he planted for her. Part dominatrix, part no-bullshit New York chick, part criminal with that brass knuckles/switchblade combo, I wouldn’t dare any New York tough guy to mess with her under any circumstances. She’ll fuckin’ shank ya! I’ve always been a sucker for leather because leather is always a statement. Rene Russo as Catherine Banning is all statements all the time until Thomas Crown keeps changing the questions. She’s always a step behind Crown, but I think over a long enough timeline, she’s ultimately going to get the better of him at some point. She’ll probably be wearing something like this leather ensemble when she does.

Liv Tyler in Empire Records

So let’s go from one hot ass pair of boots to another. Here’s Liv Tyler in Empire Records. According to an article I found from Vogue, those boots were Tyler’s own little “fuck you” to the studio who changed her outfit at the last minute to the iconic sweater/skirt combo we all got.

Two thoughts about that: A) Kudos to the studio for the change because this is maybe my favorite outfit from any movie, ever; and B) Kudos to Liv Tyler for knowing just how to put the right flourish on this thing to finish it off. Can you picture this outfit with any other footwear? That’s a hard no.

I’m likely talking out of my ass here, but a phrase I keep thinking about in terms of 90s fashion is “tough femininity.” Liv Tyler’s portrayal of Corey clearly delights in being a girl with her puppy dog crush on Rex Manning and her moderately revealing outfit, but she’s also ready to kick anyone’s ass at a moment’s notice. She screams at her boss that she’s bringing Rex his lunch. She basically assaults AJ when she thinks he’s not going to art school.

And I suppose it’s in that “tough femininity” contradiction that most of my favorite types of things exist. Never be too on-the-nose. Always have at least one element that feels anachronistic. Always keep ‘em guessing. I like to think the universe rewards bold choices.

Like writing nearly 2,000 words about women’s fashion and hoping not to come off like too much of a horse’s ass?

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