The Philadelphia Story (1940)

It’s hard to believe this today, but there was a point in time when Katharine Hepburn was considered box office poison. Literally. The Independent Theatre Owners of America put her on a list of actors in an article titled “Box Office Poison” in 1938. She’d starred in a series of flops in the mid-30s and was seen as “difficult” to deal with by members of the film press. After Howard Hughes bought the rights of the story for her, Katharine Hepburn intended The Philadelphia Story to be her comeback picture. And boy, what a comeback it was.

The love triangle between Cary Grant, Jimmy Stewart and Hepburn here forms the backbone to one of the consensus greatest romantic comedies in film history. The Hays Code’s strict rules about infidelity meant that it dealt more in subtlety than tawdry sex. The Philadelphia Story has a more nuanced view of romance than many movies today. Not bad for a movie made 77 years ago.

Grant: Gray suit with peak lapels, white dress shirt with French cuffs, and black tie.

But this wonderful film poses a specific problem when viewed from a sartorial angle: It all takes place over the course of about 24 hours. There are some outfit changes—as it was a more civilized time, Jimmy Stewart gets to wear a beautiful tuxedo—but they’re all very contained and stuck to the time of day that we see the characters. (Pajamas and robes at night, etc.)

1940 was a transition year for men’s fashion. Suits were getting bulkier, waists were getting higher, and neckties were getting shorter and wider. But Grant, Stewart and Hepburn’s boorish fiancé are still a far cry from the walls of fabric they’d be wearing a few years later. These suits are still relatively fitted, and their pants sit at the belly button, not the nipples.

Stewart: Pinstriped double-breasted suit, striped shirt, striped tie and suspenders. Grant: Gray suit with peak lapels, white dress shirt and black tie.

Double-breasted suits and three-button jackets are more difficult to find off the rack these days, but the fit of these suits is still very achievable on a budget. There’s more than enough surplus fabric in most suit pants for a tailor to lower the seat of your slacks so that they rest above your belly button. Pants that high might look and feel weird today, but "I'm trying to look like Cary Grant" isn't a bad excuse for taking sartorial risks.

Stewart: Double-breasted black tuxedo with peak lapels, white tuxedo shirt and black satin bow tie. Old Man: Olive check sport coat.