Thanks to the incredible fashion analysis of Tom and Lorenzo, costume design as character development has become one of my favourite on-screen elements to look for. And even before I consciously knew what to pay attention to, I’ve been an extremely opinionated and impressionable fashion consumer since I was wee. There are a good number of moments in costume design history that burrowed into my soul when I was younger, and that I’ve been trying to recreate or emulate ever since. Did I love them because they suited my personality, or did my personality adapt to them out of love? It’s a difficult one to call. Let’s get into it.
Mid-century magic
Gentlemen Prefer Blondes (1953)
Mind-blowingly enough, Marilyn Monroe didn’t go into this movie as the star. She sure as shite walked away as one, though. “Diamonds are a Girl’s Best Friend” is the obvious show-stopper here, and deservedly so, but the one that rocked my world was this knockout orange chiffon number:
This is the dress that most lives up in my mind to Jack Lemmon’s description of Marilyn’s walk as “like jello on springs.” This is the dress that I’ll be chasing for the rest of my life. And, thanks to this 1957 Ebony cover, I have reason to believe it would look great on me if it still existed.
That Thing You Do! (1996)
This movie is a canon event for me for many reasons, not least of which is that I married the female version of Guy Patterson. (She plays the bass rather than the drums, which is obviously cooler.) I’m in love with the whole cast and they’re all my best friends. The soundtrack is a no-skip triumph. I will hear no negativity about my movie.
Guy is the brains of this picture, and Liv Tyler as the fair Faye is the extremely stylish heart. Everything she wears is the height of ‘60s minimalist chic, with her little cigarette pants and high-neck sweaters. One outfit in particular has obsessed me for over 25 years, and it’s barely onscreen for 30 seconds: a black turtleneck, the neck and cuffs of which are leopard faux fur. Can you imagine?
Turn of the millennium
Out of Sight (1998)
This will be J.Lo’s first and least glamourous appearance on my list. It’s also my favourite J.Lo performance, even over Hustlers and Selena, because it’s her one that doesn’t feel like a performance. She just is Karen Sisco to me. Most of her costuming fits her work persona — the sleek and sexy tomboy who is better at her job than everyone around her is at theirs. My canon event outfit is one of the few we see her wearing at home and pretty vulnerable. Her married situationship shows up while her protective father is over, and her runaway criminal crush calls her on her land line to flirt with her.
A cropped Dolphins jersey, a topknot, and some little sweatshorts is such a regular-degular outfit. It’s essentially my uniform when I’m at home and not going to be on Zoom all day. On J.Lo, it’s a Hot Girl At Home fit.
The Best Man (1999)
I’ve talked before about how much ‘90s Black romcoms meant to me. The Best Man won’t be the last one on the list, and it’s here because of generational beauty Nia Long.
The first time we see her workaholic control freak character Jordan, she’s wearing the most incredible charcoal pinstripe power suit with a power pixie cut and (power?) plum lipstick. I still haven’t quite deciphered all of her outfit—is that a strapless dress under her jacket, or are the equally ‘90s spaghetti straps just set really wide?—but it doesn’t really matter. It’s sumptuous, it’s wool, it’s clearly bespoke, and it lets you know in an instant that Jordan Armstrong is runnin thaaaangs.
The Wedding Planner (2001)
Jenny is already back on the block, y’all. And I’ll be honest—I kind of hate this movie. This is the beginning of Matthew McConaughey’s romcom reign of terror, and his character here is just mean-spirited and morally evasive. I don’t buy him and J.Lo together, though they make more sense than her and Ralph Fiennes, and infinitely more sense than her and Owen Wilson. (Hot take: is J.Lo just bad at romantic chemistry??)
But this list isn’t about movie romances. This is about J.Lo wearing a gorgeous camel leather trench coat in her genre-defining meet cute scene. I have a preponderance of leather jackets in my closet, thanks to this one perfect one. We’ll come back to that.
Two Can Play That Game (2001)
I remember reading a review of this movie that said, “I shudder at the thought of a 14-year old girl watching this film.” Sorry to that man! That’s how old I was when I watched it at a sleepover!
I love this movie with all of its puzzling views on gender roles and why we should be in romantic relationships in the first place. Vivica A. Fox is an absolute star as Shantaé Smith, and I have all of her bright monochromatic/ tone-on-tone outfits committed to memory. Most of all, she’s on this list because every time we see her at home, she’s wearing a different silky robe. It’s that Taurus placement commitment to luxurious comfort for me, baby.Drumline (2002)
In perfect film Drumline, problematic fave Zoe Saldaña plays just regular problematic Nick Cannon’s dance team captain love interest. We won’t get into how her commitment to an obnoxious freshman with no game makes no sense; it’s clear at this point that Nick Cannon wields some kind of powerful magic over straight girls. Instead, we will get into her hair.
This is the iconic Bougie Black Girl haircut of the era. The fact that it’s dangerously close to Florence Henderson’s mullet is just part of its charm. Anyone with this haircut is an overachiever whose dad bought her a car and whose mother was homecoming queen. Stunning.
Pre-recession
Brown Sugar (2003)
Another Black romcom about a workaholic nursing unspoken feelings for Taye Diggs, only this time Sanaa Lathan is the workaholic instead of the free spirit. I love just about everything Sanaa wears in this movie. There’s her green turtleneck dress under a denim jacket number that she wears for an awkward bridal shower. There’s her chocolate leather jacket (!) over a dark chocolate velour hoodie over a white tank top. And the central look that cements Sanaa’s placement on this list is her rooftop Def Jam album release party outfit, particularly the hair.
As an overly optimistic teen, I was unfamiliar with what Tom and Lorenzo call FMO: For Models Only. As in, only a professionally pretty person like Sanaa Lathan can legitimately pull off a half-up-half-pigtails look like this.Hitch (2005)
Ah, Eva Mendes. Let me say firstly and foremostly that it’s a crime that she didn’t get a dozen more romcoms after Hitch, because she is such a ray of sunshine and seems to be having a ball. But I digress.
Eva Mendes. AKA the reason I started wearing pencil skirts and Revlon lipstick. This woman convinced me that a graphic t, jeans, and a blazer was a LOOK. Like, I went out and bought this exact t-shirt just because of this nonsense.It’s not even like that with me and The Beatles. It’s just like that with me and ‘00s-era Eva.
The Devil Wears Prada (2006)
This movie? For fashion inspo. Groundbreaking. I know, I know. But as a cultural landmark, The Devil Wears Prada simply cannot be denied. There are just too many incredible outfit moments and sooo many fashion montages set to irresistible pop music. I can’t even narrow it down to one look. I have to settle for a three-way tie between:
The olive green dress Andy wears when she’s running from pillar to post tracking down an unpublished Harry Potter manuscript (lmfao). I owned a dupe of this dress for years.
The embroidered bustier she’s wearing under said olive dress. I remain in thrall to embroidered bustiers to this day.
The immaculate white coat Andy wears during the “Vogue” montage. I just bought a white leather coat that is the daughter of this coat and J.Lo’s aforementioned Tom Ford for Gucci trench from The Wedding Planner. That’s how much of a hold these movies still have on me.
It was shockingly* difficult to narrow this list down to 10! And I’m curious—what goes on your list?