The Movie Outfit From the 2000s I’m *Still* Thinking About

Welcome to Celeb Look of the Week! An MR column wherein one member of our editorial team, once a week, waxes poetic about one celeb (or celeb-adjacent) outfit they can’t stop thinking about. This week, Leandra’s pick comes straight from the year 2000.

On April 14 in the year 2000, legions of Yeshiva day school students left class early and traversed eagerly like a cattle herd on a mission to a movie theater on 86th street to see Keeping the Faith. It was a veritable flop by most box office accounts but remains one of the more seminal films of my adolescence, if not because the plotline revolved around the triangular friendship among a priest and rabbi duo — unlikely best friends, a clerical odd couple — and their third musketeer, Anna Riley (Jenna Elfman), then certainly because she was wearing one of the best outfits of all time in a scene that lasted long enough to impress me, but short enough to invite my spending $3 to rent the movie and screenshot the hell out of it to break down its anatomy.

In the movie, Ben Stiller and Edward Norton play the aforementioned rabbi and priest, respectively, and it is never clear what their third friend Anna does (or maybe it is, I don’t know, I was very distracted by the fact that my best friend’s brother appeared in the movie as the young version of Ben Stiller), but she works from what is depicted as the stereotypical New York City executive corner office replete with floor-to-ceiling windows overlooking the whole of Manhattan, white marble floors and a headset. Most of the clothes she wears suck, but at about the midway mark, she is seen walking into a work-adjacent, Pier-side happy hour in a powder blue shell and sequined knee length pencil skirt. It is perfect. Why? Idk:

Conjecture #1: She is wearing a genuinely helpful solve for what to wear when you want to look festive, but also have to not get fired from your job.

Conjecture #2: You can’t see her shoes, which allows enough imagination for you and me to think about all the ways she could decorate her feet.

Until conjecture #3: You see her shoes and realize strappy flats are the only solution.

Conjecture #4: It is the year 2000 again, and to that point: Under eyeliner!!! I can run a complete story on this concept alone.

Also, remember flat ironing your hair so straight that when placed up in a ponytail the ends looked like sticks?

Heaven! But also, she’s wearing a shell. That means a cardigan can’t be far and I know we’ve spoken about the return of twin sets, but have we really evaluated it? There is no two-for-one deal so satisfying as a sleeveless shirt (let’s call it a fancy muscle tee) that comes with a cardigan. Think of all the permutations of outfit you can make with but two mere garments. Wear the shell solo, wear the cardigan solo. Button it up completely, leave the top 3 buttons unbuttoned, leave the bottom 3 unbuttoned, only close one. Pair it with nothing but a bra, Pair with another shirt. Or match it to your shell. Wear the cardigan around your waist as if a fanny pack that can’t hold anything.

Entireworld is making a really solid case for an updated one. Here you go:

(And here’s one more)

As far as the skirt, I used to find all permutations of pencil skirt boring because they reminded me of work and because when they’re not tea-length, they very awkwardly hit just above or below the knee thus serving as pedal pushers that prohibit stretching in public or galloping if you’re trying to imitate a horse. But I love a pedal pusher, so why am I getting in my own way?

Maybe I’m not. I’ve never been a fan of literal anything, so there is a world wherein my shell, not to be confused with the gas station, looks better with another kind of sparkly bottom:

En fin. I think that’s the whole of it, now pls excuse me I have to get dressed.

Feature image via Touchstone/Everett Collection.

Leandra M. Cohen

Leandra M. Cohen is the founder of Man Repeller.

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