The most stylish movies and TV shows from the last 40+ years
Some movies and TV shows make an impression not just because of their plot (or in some cases, despite it), but because of the characters’ style. I’m not talking about shows and movies specifically about fashion, but rather where the style played an important role or at least served as a pleasing note. Audrey Hepburn in a classic little black dress, pearls, and oversized sunglasses in Breakfast at Tiffany’s is an iconic example. But there are more recent productions that have made an impression. These are just a few of them.
Movies that changed the way we dress
Desperately Seeking Susan
The movie that launched a thousand Madonna wannabes, this film introduced the singer’s unique look to the world. From the vintage jackets to the layered necklaces and bangles to the scarves twisted in her hair, Madonna suffused every moment on screen with her unique combination of cool and trashy. This heralded a shift in fashion from trends being dictated by designers to a more “bottom-up” philosophy: the birth of street style as a phenomenon.
Flashdance
Another ’80s style bellwether, this movie spawned a craze for off-the-shoulder sweatshirts and leg warmers. I’d argue that this was the continuation of a trend toward incorporating exercise looks into everyday wear that started with leotards in the ’60s and ’70s. The look continues today in the form of comfy layered outfits of loose-fitting separates and athleisure, especially leggings.
The Royal Tenenbaums
Really, all of Wes Anderon’s movies are notable for the vintagey style of the sets and the characters’ wardrobes, but this one was particularly notable for the way that style clearly delineated each character: Gwyneth Paltrow’s emo-preppy look with her barette, heavy eyeliner, and vintage fur; Luke Wilson’s camel jacket/dark glasses/tennis sweatband combo, and Ben Stiller’s red tracksuit. The distinctive Wes Anderson look has become so iconic that it became a TikTok meme.
This was one of my favorite books for years, and then as I got older, I realized all of the, er, issues it presents (colonization, anyone?). But it’s still a great fashion movie, basically serving as an ad for Ralph Lauren (who did not do the costumes — that was Milena Canonero). I am particularly enamored by the hats that Meryl Streep wears as Karen Blixen, so much so that I once asked a milliner friend to re-create one of them. There are lots of wide-brimmed toppers paired with slim safari suits, a look that has become a classic, as well as a stunning wedding outfit complete with a hat that’s like a cross between a cloche and a crown.
Out of Africa
Clueless
Possibly the ultimate ’90s-style film — from Cher’s yellow plaid outfit to the first day of school to Tai’s pre-makeover flannel and post-makeover choker. It’s a time capsule of a minimalist moment in fashion, which can be seen in the preppier looks with fitted blouses, vests, and short skirts, but few accessories.
TV shows with style
The Expanse
I include this science-fiction series based completely on the amazing outfits sported by Shohreh Aglashdoo’s Chrisjen Avasarala, an adept power broker and politician in a system that has expanded beyond Earth. No sleek pantsuits for Avasarala — instead, she adorns herself like a magnificent peacock in a series of jewel-toned, often South Asian-inspired dresses and ensembles combined with some truly jaw-dropping statement necklaces and earrings. These ensembles are befitting of a woman who catapults herself to the position of Secretary-General of Earth’s United Nations, or, as another character dubs her, “Queen of Earth.”
Sex and the City
Love it or hate it, this series was a style game-changer thanks to the expert and creative eye of stylist Patricia Field. While Samantha, Miranda, and Charlotte were always well turned out, Carrie’s lewks were the star of the series. Somehow this woman got away with wearing a dirndl. I particularly liked the dressy-casual combos, like a jacket with a tulle skirt (a hallmark from the opening credits), but whether she was dressed for a coffee shop date with the girls or a gala, she nailed it every time.
Sunny
At first glance, the looks sported by Rashida Jones in this futuristic series look low-key and basic (except for her moonboot-like footwear). But their deceptive simplicity is a hallmark of modern Japanese fashion. Anyone who’s shopped at Muji or Uniqlo can understand the utilitarian yet offbeat appeal of such separates.
Call My Agent
When I asked around for examples to include in this column, a lot of people suggested Emily in Paris. But the outfits — on Emily at least — look too studied to be truly French in my eyes. Instead, the looks on Call My Agent look genuinely Parisian, from Andrea’s power suits to Noemie’s feminine little dresses. It was also fun to watch the style evolution of Fanny Sidney as Camille, the young agent (and secret love child of another character), from naive Provençal jeune fille to assured professional.
The New Look
I said I wasn’t going to focus on productions about fashion, but I have to go back on that. I loved the clothes Juliette Binoche wore as Coco Chanel in this miniseries — they really emphasized the designer’s mastery of women’s clothes that were more comfortable and wearable, but still chic. Too bad the show (which, to be fair, does not claim to be entirely historically accurate) also made it hard to deny that she was a Nazi collaborator. No amount of personal style can make that less distasteful.
