I hereby present to you: outfits from movies that live in my head rent-free. My house growing up sat at the intersection of dad playing music and grilling us on “Who is this??” while also emphasizing “decency” in any film that we watched as a family, if you’re picking up what I’m putting down. The result is that I have seen a fair number of older movies, and movies have always been something my siblings and I have bonded over. Really, it’s remarkable that I’m not MORE annoying as a person. As someone who has worked two costume-centric jobs as well, I always find it fascinating the context you can glean about a character when there’s a skillful costume designer on set. In chronological order:
The Philadelphia Story (1940)



I think every outfit of Katharine Hepburn’s in this movie lives pretty rent free in my head. You may have seen references to this movie while not having seen this movie — but it is hysterical! For no reason in particular, I find her pool cover-up in the first picture to be particularly chic. The broad-shouldered, column-like 40s silhouettes are to die for. Fun fact: I won “Best Accent” in a murder mystery game one time by imitating Katharine Hepburn in this movie.
To Catch A Thief (1955)
I did ask my sister if she had any input on this newsletter, and she responded with Grace Kelly’s black-and-white dress, also designed by costume designer Edith Head, in Rear Window. That one has a classic Dior look to it, but this is the one that sticks out to me — another Edith Head dress from To Catch a Thief. I also find it interesting that while on vacation in this movie, Grace Kelly’s character wears this same dress to dinner every night, styling the sash in different ways each night. So THAT’S how they packed those tiny, impractical suitcases — many of us couldn’t pack the same. If I owned this dress, I’d probably want to wear it to dinner every night, too.
High Society (1956)
High Society is a musical remake of The Philadelphia Story. If you want to see Frank Sinatra and Bing Crosby fight over Grace Kelly, watch this one. If you want to watch a better movie, watch The Philadelphia Story. Regardless, this was the first dress I thought of when I went to write this newsletter — the multicolored layers of chiffon remind me of the dress from the 2015 Cinderella remake (another dress I would pay a sizable amount to try on and walk around in for 15 minutes) and the effect is just stunning. I realized in writing this that so many of the outfits that stand out to me are actually just big gowns, for which I am both equally disappointed and grateful. As my grandma says, “everything is just so casual anymore!”
Sabrina (1956)
The first time I ever heard the name Givenchy… oh what a time in my life! I was obsessed with all of Audrey Hepburn’s movies when I was about 14, had a big poster of Audrey Hepburn on my wall, drew her portrait for a school project. This was around the time I started caring about fashion, started thrifting, altering and upcycling clothes, following fashion writers and fashion week. You know a ModCloth sale hated to see me coming. Audrey Hepburn is and was the blueprint. I actually think that this dress looks extremely uncomfortable to wear… but it’s so iconic regardless. I would be remiss if I didn’t mention Edith Head was also the costume designer for this film.
Pretty Woman (1990)
Not the one you were thinking of! Julia Roberts does not wear this outfit for long in this movie, but I absolutely love it. I think another common thread through these favorite outfits is that they all have a certain movement quality onscreen that gives them extreme elegance. Something about a silk charmeuse dress paired with this big chunky leather belt is delightful. And the hat! It’s a tragedy that we don’t do hats anymore!!
Meg Ryan’s Pajamas, Sleepless in Seattle (1993)
This particular scene is not the one I wanted to reference, but it’s the only image I could find. There’s one scene where Meg Ryan is walking around outside wearing a red coat layered over these pajamas, pondering what Tom Hanks could look like. I’m not sure why but I don’t think has anyone ever looked more cozy and more effortlessly beautiful than Meg Ryan does in this movie.
Friends, S5E2 (1998)
Not a movie, but deserved an inclusion regardless, because when I think about “rent-free” I think about this dress. I did not get a strapless wedding dress because strapless dresses are sartorially EXTREMELY difficult to fit correctly. Too big, you’re pulling it up all night. Too small, you’re pulling it up all night, and in all your pictures your elbows are pointed out like you’re doing the Chicken Dance. Jennifer Aniston is stunning no matter what you put her in, but this cocktail dress has my jaw on the floor. It’s not even necessarily the dress itself, but the fit that makes the difference. The jacquard fabric is also not something you see very much in garments outside of the 18th century or curtain panels but I find it very effective here. 10/10.
10 Things I Hate About You (1999)
I love all of Kat Stratford’s outfits in this movie, even if they’re not exactly my style, I appreciate the consistent silhouette and mixing of the same pieces. Consider me on the hunt for a berry/purple silk floral maxi skirt.
How to Lose a Guy in 10 Days (2003)


I do love the yellow dress, don’t get me wrong. This tube top-midi skirt combo has always stuck out to me as well, though. I remember seeing some video speculating about the costume designer’s choice to dress Kate Hudson in not-as-cute outfits when she’s doing her Annoying persona and in cuter, more laid back outfits when she really starts to be herself around Matthew McConaughey’s character. The scene where she wears this dress is the first of those scenes. I don’t know why I thought this skirt was blue, but it is all around a very classic monochrome outfit with some lace cutwork on the skirt — chic! I’d wear it out and about.
FINE — I’ll include one boy… Drive (2011)
This was my sister’s other immediate recommendation when I asked her about movie outfits — and how could I forget. If you’re wondering what jeans these are because you’d appreciate if the man walking around your house was wearing them, they are apparently Acne Studios. There’s also a scorpion on the back of the jacket and it looks bad as hell.
Alright, that’s all for this week — how are you doing? How’s your August going? There are over 150 of you reading Homebody now, and it’s an honor and a privilege. I hope you are soaking in the last few weeks of summer… actually, who are we kidding, that happens next month.
I love the range on this one. The 10 Things I Hate About You outfit was always one of my favorites. Kat is the reason I still feel cool in my platform flip flops 🫶🏻
Did you think that Carey Mulligan's look worked for Drive? I loved it then, but upon rewatching I wondered if she should be just a tad more... street? She looks so demure (to borrow the word of the week) compared to what her life was actually like!
This is a great reminder to watch Philadelphia Story. I read a great essay on the movie but still havent seen it (the essay is in the book The Crane Wife by CJ Hauser :)).