I love The Philadelphia Story. It’s such a fun, straightforward movie that has snappy dialogue, great acting, and like all of the films I’ve discussed on this blog, serves as a great case study for expressive menswear.

The plot is a bit silly and a bit farcical. Tracy Lord, a Main Line society heiress, is set to get swiftly re-married to a new money guy when all of a sudden, she is forced by her wily ex Dexter to allow Mike and Liz (a tabloid writer and photographer respectively) make a story out of it in order to prevent her father affair from going public. If this sounds like a comedy-play, you’re right; just like The Shop Around The Corner, this flick is also based on a theatrical production. But that’s a good thing! Each of the lines is expertly done, with an eloquence and grace that are certainly characteristic of Golden Era Hollywood.

The Philadelphia Story is famous, for saving the career of Katherine Hepburn and for being the only film that features both Cary Grant and Jimmy Stewart. Of course, it is the latter that matters most to menswear, which is presumably why I saw so many production photos and stills of this film across my Tumblr dashboard back in the day. It’s Jimmy and Cary in sharp suits, how could you not love it?  And that brings me to why I enjoy this film. 

You see, even though these two leading men (well, we can’t forget John Howard as the third man) wore suits in the same scene, they weren’t exactly the same.  Even in my teenagegentleman days, I could tell that there were nuances. Cary Grant’s character opted for a minimal look while Jimmy Stewart had triple stripe mixing; there was also something in their posture, the way they stood. Could their clothes be an extension of their expressive personality, even when the base (suiting) was the same? I think I was onto something! 

I initially watched clips of the movie in my youth before finally seeing the full thing as a Discord watch party with Spencer during the 2020 lockdown. Like other movies covered on this blog, it was a game of Menswear ISpy, each of us pointing at and screenshotting various fits and details. The Philadelphia Story really is a great menswear movie and can even provide a beginner some great insight into not just character-based dressing but the different rules and formalities during the Golden Era.

It’s also just a delightful romcom! 

Dexter, played wonderfully by the sauve and catty Cary Grant, is our Old (But Young) Money guy in the film. He’s comfortable and familiar with Tracy’s family (some dialogue implies that they were familiar with each other before eloping) and even has a fancy name to boot, so it is likely that he is fully aware of the decorum and dress code that characterizes Main Line society. Of course, his main uniform (or at least the most iconic look from the film) is casual: a sport shirt (with runaway collar), a lapel-less jacket, cream trousers, light socks, and loafers. It makes for a slouchy and luxurious look, one that echos the vibe and proportions of tailoring but is much less formal than a suit; think of it like the proto-version of the tonal athleisure looks we see today (sportswear!). He even wears this to wed her (again) in the climax of the movie! There’s no stuffiness with C.K. Dexter Haven! 

When Dexter does wear a jacket with lapels, it always has peaks. We see this right at the beginning of the film when he wears a thin striped, peak lapel SB jacket paired with [presumably] grey flannel trousers. The combination comes off as morning dress-esque (which has striped trousers with a black jacket) but that may be my menswear-piled mind. What is interesting is the three-button closure (rolled gently to the 2), which can feel a bit English as those suits tend to be a hard three-button peak. This type of suit makes for an elegant and formal vibe, which coincides with class and background; notch lapels would be too “normal”.  Dexter keeps this configuration in the windowpane suit he wears when introducing Mike and Liz to the Lords. It seems he has a consistent sartorial approach if not for the use of a DB at the Spy magazine office! 

Dexter’s use of plain shirts and solid ties also plays into this very formal and streamlined aesthetic. He does not delve into stereotypical Esquire Man territory by wearing striped shirts and foulard ties. He’s not a dandy! Dexter likes to keep things clean and suave, much like his personality. With all the elements put together, he appears incredibly elegant and easygoing while he messes with Tracy.

Jimmy Stewart’s Mike Connor is certainly well-tailored throughout the film, but his style contrasts quite strongly with Dexter’s streamlined duds. Mike is a working guy, a gruff intellectual who has a day job writing for a tabloid– and this is shown right through his attire.

He starts out by wearing a 3-roll-2 suit which features a diagonal weave tweed; it’s certainly a more casual and “utilitarian” garment when compared to Dexter’s more formal garb as well as Mike’s boss Kidd (who wears a 3PC SB peak in magazine office scene). This dressed-down effect is echoed by his choice of shirt and tie: a Bengal stripe spearpoint and tonal plaid tie worn sans collar bar (the use of a hat is also quite casual). Even though the suit fits him well, it doesn’t compare to the decidedly business-pointed, pinstriped DB worn by Dexter.

When Mike is introduced to the Lords, he wears a pinstripe DB suit; whether this is a suggestion or a loan from Dexter, we don’t know. Mike ends up wearing this for the remainder of the film even in the finale. The suit cuts a powerful silhouette (rivaling the one from The Shop Around The Corner), though he leaves the jacket open, showing that Mike may not prefer being trussed up.  It’s important to note that he retains his casual styling: a hat worn tilted in the house as well as pattern mixing (a Bengal stripe and a block stripe tie). It’s great to see his blase and lightly cynical attitude reflected in his clothes, especially when you see him next to Dexter. The two couldn’t be more different! 

That being said, Mike looks incredibly at home in an evening suit (tuxedo). It’s not confirmed if this is a gift from the Lords or Mike’s own (he does ask if he needs white or black tie), but it fits like it was made for him. The tuxedo is a 4×2 DB and he wears it with a point collar that is seemingly a normal shirt with pearl buttons rather than studs; there is also no use of a pocket square, making the rig feel quite impromptu by Golden Era standards. But damn if he doesn’t look good in it! The only thing is that the wedding eve party is indeed a white tie affair, and so Mike’s dinner suit sticks out among the tailcoats, wing collars, and pique bow ties worn by Kittredge, the Lords, and their guests. Such is the power of menswear! 

Finally, we have George Kittredge, Tracy’s current betrothed, and a relatively New Money type played by John Howard. He’s a relatively nice man but you can tell that he’s trying really hard to fit in within Main Line society and be the upper-class person he has always aspired to be. This is clearly shown in his first appearance where he shows up in pristine riding attire: a derby hat, riding jacket (cut in a paddock way), and jodhpurs. Tracy even teases him with how new and clean it all is.

His main suited look is an interesting one. Kittredge opts for a plain (or faintly patterned/woven) DB suit, though unlike Mike, his is a 3PC, upping the formality just a smidge. There are no striped shirts or collar bars here (showing a clean look like Dexter) but Kittredge makes a bold move with a crescent motif tie, the first and only foulard in the film. It’s quite a fun addition, which contributes to his interesting character; he’s rich and powerful now but he has his roots in the everyman. 

Kittredge spends the rest of the film in the extremes of menswear, white tie, and morning dress. Both of these dress codes are quite similar, being a tailcoat, waistcoat, wing collar, and trousers (though in morning dress the trousers are striped). Kittredge looks fantastic in them both, with the tailcoat in particular being cut quite sharp. It’s easy for these largely anachronistic modes of dress to look a little dandy but damn does he look good in them. 

The boys and I talk a little bit more about the film and its menswear in the latest bonus episode! You can listen to a clip above (where I reference a certain someone’s recent stomach issue) but you’ll have to subscribe on Patreon for the full episode! 

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Buh-bye!

Ethan M. Wong (follow me on IG)| StyleandDirection

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