19 Thoughts I Had Watching Head Over Heels, a Forgotten Fashion Flick

Fashion movies like The Devil Wears Prada or Zoolander get all the fanfare, but when it comes to campy aughts fashion, nothing beats Head Over Heels. Released 20 years ago today, it’s the best stylish flick that you’ve probably never seen. The plot of this comedic B movie centers around Amanda Pierce (Monica Potter), a paintings conservator at the Met, who moves in with four roommates who are up-and-coming models in New York. There’s Jade (Shalom Harlow), who all the men fawn over; Roxana (Ivana Milicevic), the tough-as-nails Russian; Candi (Sarah O’Hare), the bubbly Australian; and Holly (Tomiko Fraser), the smarty who could have gone to Stanford but instead quips, “Look at me, what do I need Stanford for?”

Things get interesting when Amanda meets Jim Winston, played by Freddie Prinze Jr. (the heartthrob of the 2000s). He lives in the apartment across from the five roomies, and from their loft, they can actually see into his place (creepy, I know). One night, the girls believe they’ve witnessed him murdering a woman, and become convinced he’s a psycho killer. It’s a loose take on Alfred Hitchcock’s Rear Window, and sure, there’s lots of twists and turns to go with it—but that’s not why it’s worth a watch today: the early-Y2K fashion is! 

The film is essentially a time capsule of what was trending in fashion at the time. The four models are decked out in the hottest clothes from the era: They wear chic slip dresses and faux-fur coats as they investigate if the hot guy next door is a serial killer or not. The fashion is so absurd at times—especially for a murder-mystery setting—yet that’s what makes it so great. It’s your next guilty-pleasure watch. The movie’s 2000s aesthetic is also so hot right now, with brands like Juicy Couture and Von Dutch having a comeback, so I decided to revisit the film to see if the style still feels current. (Spoiler: It does. For the most part.)

Below, 19 thoughts I had while rewatching Head Over Heels.

1. We meet Amanda at her day job as a paintings conservator at the Met. I find it funny that she’s carelessly drinking a coffee around a painting that I assume is priceless. Fire her!

2. A two-second Timothy Olyphant cameo as Amanda’s cheating boyfriend? Not mad at it.

3. Amanda moves out of her boyfriend’s house and sees a flyer for a “roommate wanted.” The room is advertised as going for $500. In Manhattan?! Jealous. 

4. We meet the four fabulous models who Amanda is going to move in with. They live in a huge loft with sprawling ceilings and a fabulous walk-in closet that they all share. “How can they afford this?” I seethe. 

5. We learn that it’s actually a model’s apartment that their agency pays for. Okay, fair enough, that’s a real thing. 

6. Let’s take a moment to acknowledge Holly, who is wearing a chic floral dress that is very Brock Collection. 

7. As Amanda moves into the apartment, she notices a line of men waiting outside, all suitors hoping to get a date with one of the models. The girls are picky, though. They peak through the peephole: “His suit is Hugo Boss, but it’s straight off the rack. His tie’s a Gucci knockoff. Those shoes? That’s between him and Payless.”

8. Amanda spots Jim (Freddie) from across the way. They can see everything he does. She instantly becomes smitten with him (especially after seeing him do pull-ups shirtless). 

9. I’m not loving the stereotype of Candi having different surgical bandages on her face throughout all of her scenes. Not all models get plastic surgery, okay! Most are just genetically blessed—which, I know, unfair. 

10. Jade’s vampy leather bustier top is what all TikTok e-girls are wearing right now. How good was it that they got Shalom Harlow, an IRL supermodel, to play her? A+ casting choice. 

11. Roxana is casually lounging on the couch in tight red sequin pants. Is this what models really wore in 2001?

12. The models decide to give Amanda a makeover. This was such a 2000s movie thing: a “makeover” that just consists of a different outfit and, like, some lip gloss. I gotta say, though: I do love this black dress with a faux-fur trim that they put her in. 

13. Amanda is supposed to be the unfashionable one of the group, but her black square-neck top and silk skirt is super chic. Not sure why they all dressed up to break into Jim’s apartment, though. 

14. Back at their apartment, Holly says she’s booked her first big runway show at New York Fashion Week tomorrow. She’s practicing by walking with a book on top of her head (for posture). A classic trick! 

15. At said NYFW show, Holly is now in her full runway look, which is a pink dress with marabou trim. I’m getting major Anna Sui vibes. 

16. I’ll skip over the major plot points so as not to spoil anything, but now we’re in a clothing warehouse where the girls are being held captive by a bad guy. (Things took a turn.) “I can’t die here,” says Candi. “This place is full of ugly dresses!” If that isn’t a mood, what is?

17. Now we’re back at NYFW. All the girls, including Amanda, are walking in a show as a covert operation to catch another bad guy. (Yes, really.) Amanda is put in a black tulle gown with a lacy shawl. “I look like Stevie Nicks,” she says. I have to admit, this is the first look that doesn’t hold up. It’s too much.  

18. Judging by the frilly white gown and dramatic top hat that follows Amanda’s look in this “runway” show, for a faux designer named Alfredo, this entire collection is a flop. 

19. Joke’s on me. Despite several models tackling someone on the runway, the fashion critics adore the collection. “Leave it to Alfredo to bring a sense of theater back to New York fashion,” a reporter says. Well, fashion does love drama!