7 Stylish, Hilarious Retro Rom-Coms and Their Coordinating Cocktails
In my apartment, Sundays are strictly reserved for pancakes, cappuccinos, face masks, scented candles, and classic cinema. Okay, well maybe not strictly because Sundays are truly a day for doing whatever you want—at least, in my books. And according to moi there is hardly anything better that winding down the weekend with a retro rom-com and cocktail pairing.
I’ve been a retro rom-com lover since I was a pre-teen and discovered Breakfast at Tiffany’s. From that moment on, I was obsessed. I’ve seen every Audrey Hepburn movie 1,300 times over. Even my first tattoo was inspired by Ms. Hepburn. She’s just so glamorous, beautiful, kind—exactly the kind of woman I wanted to be when I grew up.
And now that I’m grown, I still try to emulate her style and grace in everything I do.
Fun fact: My other fashion blog The Lady-like Leopard got its name by combining my love of Audrey and classic cinema (lady-like) with the fierce side of my personality that pounces after my dreams and goals with a wildly uncontrollable ferocity (leopard).
As I say in my bio, when I’m not at my computer, there’s a good chance you’ll find me laughing hysterically alongside a retro rom-com. I am a total sucker for a gut-busting romantic comedy—especially when it’s paired with a delicious cocktail.
7 Stylish, Hilarious Retro Rom-Coms & Their Coordinating Cocktails
Charade, 1963
Starring: Audrey Hepburn, Cary Grant
As I said before, I’m down for anything with Audrey Hepburn. And even though Blair Waldorf rudely said that she doesn’t like Charade, I love it. How can you go wrong when you add Cary Grant to the mix? This movie starts out on a ski trip in Megève and ends in Paris; it’s glamour from beginning to end. There are spies, mistaken identities, and lots of leopard prints.
Cocktail: Sidecar
2 oz. of Cognac
1 oz. orange liqueur
¾ oz. lemon juice
Lemon peel or orange peel
Pour all ingredients into a cocktail shaker. Add ice and shake well. Strain into a coupe. Garnish with a citrus twist.
Some Like It Hot, 1959
Starring: Marilyn Monroe, Tony Curtis, Jack Lemmon
This movie will literally have you falling off the couch. I swear, I was howling through the whole thing. It gave me my new favourite catchphrase “zowie!!!” and gave me serious outfit goals with Marilyn Monroe’s enviable looks. I only saw this one for the first time during the pandemic and trust me, I’ll be watching it many more times over. Marilyn loves Manhattan cocktails so much that she sneakily consumes them out of a hot water bottle… I recommend sipping from a glass.
Cocktail: Manhattan
2 oz. bourbon or rye
1 oz. sweet vermouth
2 dashes Angostura bitters
1 dash orange bitters
Brandied cherries
Add everything into a mixing glass with ice. Stir until chilled. Pour into a cool coupe. Garnish with a brandied cherry.
Pillow Talk, 1959
Starring: Rock Hudson, Doris Day
A genuine hate-to-love (literally) comedy about two stylish people with a shared phone line. Can you believe that used to exist? How annoying. I definitely feel Doris Day’s pain. The deceitful sweet-talking in this movie is riveting. Guaranteed you’ll laugh and lust after the fashion—and maybe how handsome Rock Hudson is. (Don’t judge, you know he’s a hottie.)
Cocktail: Champagne cocktail
1 sugar cube
Angostura bitters
Champagne
Lemon or orange twist
First, soak the sugar cube in Angostura bitters. Then, drop into a champagne saucer or flute. Top with a champagne (or let’s be real, sparkling wine). Garnish with a fresh citrus twist.
How to Marry a Millionaire, 1953
Starring: Lauren Bacall, Marilyn Monroe, Betty Grable
Not only is this movie super funny, it’s beyond stylish. Lauren Bacall is a bad-ass bitch who schemes her way into living in a gorgeous penthouse. Then, she has to sell all of the furniture to pay for her extravagant lifestyle and the goal of all three women: finding filthy rich husbands. They drink a lot of champagne in front of the Manhattan skyline and are always dressed in gorgeous garb.
Another Marilyn Monroe movie that I completely adore is Gentlemen Prefer Blondes. I mean, the Diamonds Are a Girl’s Best Friend scene is just way too iconic. Marilyn’s pink dress! The jewels! The dapper gentlemen!
Cocktail: A bottle of champagne
Champagne, champagne, and more champagne! If you’re not looking to break the bank on a bottle of genuine luxury, try a sparkling wine. Two of my favourites are “the good sparkling” by Saintly Wine and LOLA Secco by Pelee Island Winery.
Man’s Favourite Sport?, 1964
Starring: Rock Hudson, Paula Prentiss
Man’s Favourite Sport is about fishing—but don’t let that fool you. Even non-fishers (especially non-fishers) will find this movie so unbelievably charming that you’ll almost want to grab a rod and head out to the lake yourself. Think: Two people that are meant to be together but plot twists and sassy zingers prolong the inevitable.
Cocktail: Fish Eye
3⁄4 cup fresh pink grapefruit juice
3 oz. light rum
2 tablespoons fresh lemon juice
1 1⁄2 tablespoons fresh lime juice
1 tablespoon sugar
Stir all of the ingredients in a pitcher. Pour over ice and enjoy. Optional: Garnish with a lime wedge.
Funny Face, 1957
Starring: Audrey Hepburn, Fred Astaire
Not only is Audrey Hepburn my favourite actress of all time, in Funny Face she loves books and then makes the move into fashion. Two of my favourite things! In a way, that’s what I did with my life but in reverse. There are so many iconic retro rom-com moments in this movie—from the “pink” scene at the Quality Magazine office to being photographed in front of famous Parisian landmarks. All of the outfits are simply to die for, darling.
Cocktail: Pink Lady
1 1⁄2 oz. gin
3⁄4 oz. applejack
1⁄4 oz. fresh lemon juice
2 dashes grenadine
1 egg white
Maraschino cherries
Pour all of the ingredients into a cocktail shaker. Vigorously shake for 30 seconds. Strain into a chilled cocktail glass. Garnish with a cherry—or five. Serve and sip!
Designing Woman, 1957
Starring: Lauren Bacall, Gregory Peck
The fifties killed it when it came to romantic comedies. These two main characters, Lauren Bacall and Gregory Peck (you probably recognize him from Roman Holiday), are so polar opposite yet fall in love and jet across America to begin their far-from-blissful life together. She’s a high-society fashion designer and he is a blue-collar sports reporter. Their chemistry is beyond fabulous.
Cocktail: Aviation
1 1⁄2 oz. gin
1⁄2 oz. lemon juice
1⁄2 oz. maraschino liqueur
Crème de violette
Add all ingredients to a cocktail shaker filled with ice. Shake and strain into a glass. Garnish with a cherry.
Which retro rom-com and cocktail pairing will you be trying first? When the world opens up again, here are three stylish places where you can go IRL and get an aviation cocktail—my personal favourite. Hope to toast with you soon.
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Feature image by pure julia on Unsplash