25 Style Lessons You Can Only Learn From These NYC Films

You might just find your next outfit inspiration as you pour over these style-savvy looks, which let’s face it, have made the following film characters part of the fashion zeitgeist, even though they only live on screen.

A cult classic and guilty pleasure, the cinematic adaptation of Jacqueline Susann’s 1967 novel is filled with sex, drugs (aka dolls), and fashion. With bombshells Barbara Parkins (as good girl, Anne Welles), Patty Duke,(as up-and-coming singer Neely O’Hara), and Sharon Tate (as struggling actress Jennifer North). Costumes were by William Travilla (best known for Marilyn Monroe’s iconic white dress in The Seven Year Itch) and give the audience insight into the secret lives of women who navigate the fabulous nightlife scene of late ’60s Manhattan.

Style Lesson: If you can’t dress to be yourself, dress to be the woman you aspire to be.

Sure, this film is a bit of a cliché, especially for anyone who’s ever worked in publishing. And although Andy Sachs, played by Anne Hathaway, makes an impressive fashion transformation, it’s Meryl Streep as Runway‘s powerhouse editor who looks impeccable in every scene.

Style Lesson: You’ve got to know fashion rules before you can break them.

Pre-GOOP Gwyneth Paltrow dazzles as Margot Helen Tenenbaum defines bad girl preppy, a look that involves black kohl eyeliner, a single baby barrette, baby pink cashmere gloves, and a ratty mink coat. The look is timeless and complex, giving insight into Margot’s complexity.

Style Lesson: Fashion embraces the weirdos.

“I am a very stylish girl,” coos Audrey Hepburn as Holly Golightly, the quintessential New York party lass, making the understatement of the century. There isn’t a girl who moves to New York who doesn’t idolize Holly. Much of this aforementioned admiration is owned to her elegant, understated, but eccentric look. From blonde-streaks, to her white man’s shirt (designed by Paramount’s star costumer, Edith Head) to the black Givenchy gown that opens the film, it’s impossible to imagine any one but Hepburn in this role. But, according to Classiq, Capote had envisioned the role for Marilyn Monroe.

Style Lesson: Never, ever leave the house without sunglasses.

From Staten Island to Wall Street, the city serves as a metaphor for the transformation of this working girl (secretary-turned-executive Tess McGill, played by Melanie Griffith), but so too does her wardrobe. As a secretary, Tess had big hair, big earrings, and lots of blue eyeshadow. But when she decides to climb the corporate ladder (in the running shoes she wears en route to the office), she chops her hair, replaces hoops with pearls, and tones down her makeup. As for her wardrobe, there’s lots of sleek black dresses and power blazers that epitomize the 1980s New York female exec.

Style Lesson: Go big or go home. And going home really isn’t an option.

Well, la-di-da, ladies. Diane Keaton as the title role in Annie Hall is a major style crush for women who like to dress in men’s clothing. Annie is as quirky as her ensembles, decades before androgyny was all the rage.

Style Lesson: Women can wear anything that men can wear. #feminism

Chloë Sevigny and Kate Beckinsale star as two recent college grads who by day work in publishing and by night boogie at Studio 54. Costume director Sarah Edwards worked hard to create a post-disco/pre-yuppie look that dominated the streets of New York in the early 1980s. Dazed has named this film one of disco’s saving graces because of the carefully curated items that go beyond polyester and sequins.

Style Lesson: Your 20s are an ideal time to experiment with zeitgeist-driven trends.

Although the “love story” begins in Boston, New York is the backdrop for melodrama that makes this classic tear-jerker one of Manhattan’s most stylish films. Why? Two words: Ali McGraw. As Jenny Cavaleri, McGraw takes preppy-chic to the next level, and rocks one of this fall’s must-have items: the cashmere camel coat.

Style Lesson: Preppy essentials are comfortable to wear, while making you look put together.

Rosie Perez opens the 1987 Spike Lee “joint,” Do the Right Thing dancing in a red spandex number shaking her booty and doing the Roger Rabbit to Public Enemy’s “Fight the Power.” As the opening credits evolve, so does Perez’s costume. She’s suddenly wearing silver boxing trunks, boxing gloves, and not much else. As Tina, Perez brings late ’80s Bed-Stuy style to the rest of the world, proving homegirls serve looks that are on fire.

Style Lesson: If you’ve got it, flaunt it.

Jane Fonda is a high-class escort in Klute, in which her powers of seduction help solve a crime. The role earned her an Academy Award, but her character, Bree Daniels also gets major fashion props for her thigh-high boots, t-shirts sans bra, trench coat, lots of suede and the most tasteful fringed accessories, culled by costume designer Ann Roth. In short, if you want to conjure a chic ’70s vibe, watch this film immediately.

Style Lesson: When you wear vintage, it should never look like a costume.

Diana Ross inhabits the life of Billie Holiday in this 1972 biopic about the tragic life of the trailblazing jazz singer. From the gorgeous gowns to the Bob Mackie wool/fur ensemble, Ross is as style-making as the woman she embodies. Plus, the white orchid behind her ear not only elegance, but Billie’s fragility.

Style Lesson: When recreating an iconic look, let your inner fierceness shine.

A young Angelina Jolie portrays one of the first American supermodels, Gia Marie Carangi, who graced multiple Vogue covers and campaigns for Yves Saint Laurent, Christian Dior, and Versace, before dying from an AIDS-related illness. Costume designer Robert Turturice conveys Gia’s transformation from punk rock tomboy to glamour girl, while tracing the supermodel’s rise to fame and tragic fall.

Style Lesson: You don’t have to be a fashion chameleon, but versatility is the mark of a style-savvy woman.

Desperately Seeking Susan’s director Susan Seidelman tells The Cut that she cast Madonna for the part of Susan because the singer injected an authentic downtown vibe to the set (after all, Madge was close friends with Jean-Michel Basquiat and Keith Haring). Susan’s mismatched outfits, rocking leather and lace and making the look cohesive helps convey not only her character, but the downtown New York art scene of the mid-1980s.

Style Lesson: You can’t fake attitude; you either have it, or you don’t. If you have it, you can wear anything and make it work.

Did you know that it was in the actress’s contracts that they could keep all the wardrobe from the film? With Pat Field on hand for the Sex and the City films, the gang paraded in every label on the planet, and even though the films might have been weak on plot, the clothes were to die for.

Style Lesson: Treat your closet like a palace, and keep a strict “keep, store, toss,” policy.

No one was expecting KIDS to change the way Americans looked at youth culture, but that’s exactly what happened after this 1995 independent film directed by Larry Clark was released. Capturing mid-1990s Manhattan street kids, (and their looks) Rosario Dawson as Ruby and Chloë Sevigny as Jennie prove that jeans and a t-shirt never go out of style.

Style Lesson: You don’t have to vamp it up to be sexy, casual cool can be just as alluring.

Alfred Hitchcock’s favorite designer and mid-century darling Edith Head didn’t have to do much to make the stunning Grace Kelly a fashion girl’s dream in Rear Window, but she did provide Kelly’s character, Lisa Fremont. with stunning looks for this thriller. Prefiguring (and inspiring) Dior with this full crinoline look, (pictured above) Head gave Lisa’s socialite character a wardrobe fit for a princess. From her charm bracelet to her white gloves, pearl earrings, and impeccable hair and makeup, Lisa’s look is cohesive from head-to-toe.

Style Lesson: Pay attention to statement making accessories, but wear them discerningly.

Bai Ling’s look as “Peep Show Girl,” a feisty sex booth worker in the early aughts thriller Edmond, is not for the faint of heart. With an itsy-bitsy bikini, pink wig, and giant flower hairpiece, “Peep Show Girl” is a sexpot come to life. This isn’t a look you can wear outside the bedroom, but the electricity of Ling’s wardrobe ensemble can certainly give your sartorial choices a charge.

Style Lesson: Bold choices attract attention, but not as much as your confidence to wear them.

Laura Mulleavy of Rodarte is responsible for creating the white and black swan looks in the creepy horror ballet film, which earned Natalie Portman an Academy Award for playing prima ballerina on the brink of destruction. Jewel-encrusted costumes, feathered headpieces, and tutus that are works of art drive home the film’s message of the painstaking process involved in the creative arts.

Style Lesson: Sometimes you have to put on a costume to find out who you really are.

Blonde bombshell Margot Robbie stars as Jordan Belfort’s wife, Naomi Lapaglia, in the Scorcese/DiCaprio vehicle that’s a cautionary tale against greed. As the film was set in the ’90s, Naomi wears ostentatious-curve hugging numbers that do what they’re meant to do: depict Naomi as walking sex.

Style Lesson: When the opportunity calls for it, go commando.

Jodie Foster was 13 when she starred as Iris “Easy” Steensma, a street-savvy prostitute who’s down with women’s lib and can hold her own opposite an idealistic taxi driver (Travis Bickle, played by Robert De Niro). In stark contrast to Travis’s love interest, elegant Betsy (played by Cybill Shepherd), Iris is the epitome of ’70s boho chic. Her floppy hat, hot pants, and oversized sunglasses are in-step with the hipster aesthetic you can find on the streets of New York today.

Style Lesson: Anyone can rock a trend, but a true fashion girl knows where her style lies.

Lelia Goldoni stars as Lelia Carruthers in the John Cassavetes classic Shadows, and possibly becomes Manhattan’s first well-known “it girl.” The thick brow, heavy black eyeliner, and art deco earrings signal Lelia knows how to rock cocktail hour and how to stand out in a little black dress.

Style Lesson: Black is never boring when accessorized with strong hair, makeup, and accessories.

The cult hit Party Monster showed audiences that Macaulay Culkin is all grown up, as he portrays a murderous club kid in mid-1990s Manhattan. Chloë Sevigny, who came-of-age in the real ’90s club scene, plays Gitzy, a fellow-club-goer who helps translate the film’s prophetic message: if you put yourself out there as a brand, people will follow you. Of course, taking fabulous looks to the next level is required in this post-Warhol era.

Style Lesson: A little glitter goes a long way.

Betty Grable, Lauren Bacall, and Marilyn Monroe in Technicolor bring Manhattan glamour as a trio of fashion models in this classic film. William Travilla, who worked closely with Monroe during her career, gives equal attention to all female leads, as each character’s look reflects her personality. That alone is quite a stylistic feat, given that Monroe’s star power was at its peak during the film’s release.

Style Lesson: When in doubt, seek the advice of a pro to play up your best features.

Sandra Bernhard’s Masha in The King of Comedy might be a little unhinged, but the woman knows how to rock some serious eyewear. Although the film was released in 1983, Masha’s sunnies bear a striking resemblance to Celine’s “Shadow Glasses,” which came out in 2016, and nearly sold out.

Style Lesson: Fashion is cyclical, so find your next look by looking to days gone by.

The pixie cut, baby doll dresses, school girl pea coat, and beret ensemble (pictured above) leave audiences with no doubts that Rosemary Woodhouse (played by Mia Farrow) is a dewy-eyed naïf who just happens to give birth to Satan’s progeny. The Dakota, with its gothic architecture, where Rosemary and her husband feather their new nest, couldn’t be a better backdrop for an apartment building that houses a coven of witches.

Style Lesson: Just because your look is demure doesn’t mean you can’t wield a knife like one bad mother.