Living in a true four-season city like New York (and being from an infamously cold state like Minnesota), I feel a constant pull to take full advantage of warm weather—filling my weekends with park picnics and my workdays with outdoor writing sessions whenever possible. And when the inevitable violent thunderstorm or sweltering heat wave forces me inside, I try to keep the party going by putting on a particularly summery movie.
I won’t attempt to play film critic, because movie taste is highly personal. But I think many of us can agree that watching something set in the summertime is a uniquely visceral experience—often involving a delightful mix of escapism, optimism, mood-boosting music, and, of course, aspirational style.
As I think about summer movies, there are so many good outfits that come to mind, so I’ve compiled the ultimate list of films featuring female characters who not only have timeless summer style but are also especially self-assured—something we always strive to be.
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We’re all familiar with the black ensemble from Grease, which makes its appearance when Sandy Olsson (played by Olivia Newton-John) shows up to graduation with newfound confidence. Fulfill your big-reveal fantasy by swapping out your go-to Power Casual pants for the vegan leather Harrington legging and shoulder-baring Dae top. Complete the look with a minimalist belt and gold hoops, and instead of Sandy’s red stilettos, opt for a low-heeled, refined black slides.
The dance moves of Frances “Baby” Houseman (played by Jennifer Grey) in Dirty Dancing aren’t achievable for most of us, but her casual style certainly is. Try an elevated version of her fitted tank, light blue shorts, and white sneakers, and don’t let your two left feet discourage you from busting a move. Prefer pieces with more structure? Go with the not-too-short, Better Than Denim Caitlin shorts, and top them off with a black leather belt.
As a baseball movie that takes place in the 1940s, A League of Their Own involves a lot of retro uniforms. But we’re here to talk about personal style. And while the highly poised Geena Davis plays the lead character, her feisty younger sister Kit Keller (played by Lori Petty) holds her sartorial own. One of her style moments reminds me of one of my favorite M.M. sets: the Wren top and Amelia jogger in arpeggio print. Like Kit’s dress, this set features a geometric blue pattern that’s retro and modern all at once. We recommend dressing it up with a heeled sandal.
It’s hard to beat a feel-good rom-com like How Stella Got Her Groove Back, which involves not only a meet-cute but also a supportive best friend, an enviable vacation, and fantastic resort wear. Achieve the beachy aesthetic of Stella Payne (played by Angela Bassett)—who demonstrates that even high-powered stockbrokers can unwind in the right environment—with the airy knit Melody tank, lightweight Shane pant, and sand-friendly Koio slides. This movie also deserves major credit for being ahead of its time in addressing the theme of balancing a career and motherhood.
Watching The Parent Trap on repeat as a child, I always envied the twins’ clothing, and now, I admire the sharp workwear of Meredith Blake (played by Elaine Hendrix) and the English elegance of Elizabeth James (played by Natasha Richardson). But, since I cannot in good conscience endorse the devious ways of Meredith Blake, I’ll focus on Elizabeth James. As a wedding dress designer who dresses her 12-year-old daughter in full suits, Elizabeth’s style is incredibly sophisticated—but somehow neither fussy nor stiff. For a Power Casual take on her London look, layer the Better Than Denim Anna jacket over the chic Constance dress, and keep things elevated with metallic accessories like the Rowan flats and Etel earrings.
Spoiler alert: The Talented Mr. Ripley isn’t exactly a lighthearted movie. However, the dreamy European setting and quintessentially summery clothes are simply irresistible. Marge Duval (played by Gwyneth Paltrow) stands out with her crisp button-downs and flowy skirts. Go for a streamlined version of her look with the rust-colored Melrose skirt, a polished white T-shirt, and the low-heeled Irene slingbacks.
Blockbuster Crazy Rich Asians is known for its opulence, which includes playful, over-the-top outfits. Most of the looks aren’t exactly relatable, but I managed to find a more approachable suiting look that Eleanor Sung-Young (played by Michelle Yeoh) wears. Summer is your chance to lean into a slightly more laid-back lifestyle, so try out a relaxed interpretation of this power suit by combining the Chiara top with the matching Madelyn pant. Finish off this set with classic accessories like black flats and pearl earrings.
In The Heights is essentially a musical celebration of New York City, and summer in New York does not exist without some unbearable humidity. If you, too, dread those suffocating summer scorchers, this one’s for you. Whether you’re dancing in the streets or your window A/C unit simply isn’t cutting it, you can keep cool and polished with elevated essentials like the subtly textured Paige tank, not-too-short Caitlin shorts, and comfortable Koio slides.
I’ll admit, I was not all that interested in seeing Top Gun: Maverick, but the aerial stunts and Penny Benjamin’s easygoing San Diego style had me hooked. Penny (played by Jennifer Connelly) is an independent spirit who owns the local watering hole. Her style is characterized by lots of nautical knits, as well as this Power Casual look that you can copy to near perfection with the olive Langley bomber, button-down Tatum top, medium-wash Frame jeans, white Koio sneakers, and delicate single bezel necklace.