The timeless glamour of stars like Marilyn Monroe, Audrey Hepburn, and Grace Kelly has inspired women throughout the ages — and the popularity of shops like ModCloth and Unique Vintage is a testament to the fact that classic Hollywood style will never go out of fashion.
Forget about fur coats and ball gowns, though — in real life, these icons shined the brightest when they kept things casual. Sticking to neutral, tailored basics, accessorizing with signature pieces, and adding a pop of color with a rich, vibrant lipstick was the key to these stars’ seemingly effortless style.
If you’re ready to trade in your comfortable house dresses and workout wear for a more tailored look, you’re in luck. We’ve rounded up six outfits that Marilyn, Audrey, Liz, Grace, Katharine, and Lauren might have worn — and even found a shade of lipstick to go with every look.
Keep scrolling to shop our picks that emulate the classic Hollywood style of your favorite leading ladies!
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How To Dress Like Marilyn Monroe
When we hear the name Marilyn Monroe, we usually think of the blonde bombshell clad in that infamous magenta gown, charming everyone with "Diamonds are a Girl's Best Friend" as she drips in diamonds (talk to me, Harry Winston, tell me all about it). But offscreen, Marilyn liked to take her glamour down a notch, opting for carefully tailored basics like this neutral black-and-white ensemble.
To recreate this look, we suggest pairing a rolled-up black mock-turtleneck sweater ($33.99, Unique Vintage) with a chic pair of ivory pleated ankle pants ($159.20, Nordstrom). Top if off with a swipe of ever-flattering coral lipstick — we love Charlotte Tilbury's Matte Revolution Lipstick in the shade Sexy Sienna ($34, Sephora) — and you'll have the look down!
How To Dress Like Katharine Hepburn
With four Academy Awards to her name and a list of timeless movies under her belt, like The Philadelphia Story and Guess Who's Coming to Dinner?, Katharine Hepburn is one of most enduring stars Hollywood has ever known. And just as she made waves in film, she was also a trendsetter in fashion. While usually found in a crisp button-down shirt and slacks, Katharine was also an expert at embracing her femininity with stylish coats and modest dresses.
To recreate this look, all you need is a classic peacoat ($219, L.L. Bean) and a stylish polka-dot dress ($78, Unique Vintage). Add a finishing touch with Too Faced's Peach Kiss lipstick in the shade 'Chill Pill' ($34, Sephora).
How To Dress Like Audrey Hepburn
If there's one classic Hollywood star scores of women have looked to for fashion inspriation over the years, it's Audrey Hepburn. And no other movie of hers has contributed to this than the 1961 classic Breakfast's at Tiffany's. A continuation of Hepburn's long-term collaboration with Givenchy, the film is filled with dozens of iconic looks, like this one.
To recreate this famous trench-coat ensemble, you'll need a couple basic pieces that will become staples in your closet. Start with a little black dress, like like this simple knit one from Halogen that has just enough stretch for comfort ($59, Nordstrom). Add a white silk scarf, ($79, Nordstrom), a pair of perfect black cat-eye sunglasses like these, from Prada ($272, Nordstrom), nude heels, like Nina60 Pointy Toe Pump ($78.95, Nordstrom), and, of course, a form-flattering trench coat. We love Halogen's version ($149, Nordstrom). Top it off with a lipstick inspired by Hepburn herself in the shade 'Hepburn Honey' ($34, Sephora), and you'll be giving Holly Golightly a run for her money in no time.
How To Dress Like Lauren Bacall
Affectionately dubbed, "The Look" thanks to her piercing stare on screen, from the beginning, Lauren "Betty" Bacall was a style icon. Discovered on the cover of Harper's Bazaar by socialite Slim Hawks, wife of Howard Hawks — who directed Bacall in her first film To Have and Have Not (1944) alongside future husband Humphrey Bogart — Lauren's style symbolized that of the modern American woman. Off-screen, you could find Bacall in clothes that emphasized her laidback demeanor, like this outfit.
With this slouchy knit turtleneck sweater ($128, Nordstrom), a flowing pair of wide leg slacks ($128, Nordstrom), elegant slide sandals ($189, Nordstrom), and Charlotte Tilbury's 'Tell Laura' lipstick ($34, Sephora), you'll be able to recreate this look and feel like a studio-system star without sacrificing any comfort in the process.
How To Dress Like Elizabeth Taylor
One of the most glamorous stars of classic Hollywood was none other than Elizabeth Taylor. The celebrated actress and tabloid favorite knew how to keep people talking, especially when it came to her fashion. Well-known for her exquisite style and opulent taste in jewelry, we wanted to find a way to encapsulate the most memorable aspects of her style in a way that's still wearable in an everyday capacity.
To recreate this look, pick up a striped jewel-toned top, like Paul Smith's silk button-down blouse ($276, Zappos), elegant door-knocker earrings, like ASOS DESIGN's Vintage-Engraved Earrings ($10, ASOS), and a bright-berry lipstick, like Bobbi Brown Crushed Lip Color in Cherry ($42, Sephora), to tie the whole look together in a glamorous bow.
How to Dress Like Grace Kelly
She may have been Hollywood-turned-real-life royalty, but Grace Kelly understood that glamorous fashion didn't always mean ball gowns and heels. An icon whose fashion we still adore through her on-screen looks in films like Rear Window (1954) and To Catch a Thief (1955), where she epitomized Old Hollywood grandeur, her off-screen looks were much more relaxed.
To recreate this Grace Kelly look, pick up a white button-down top, like Treasure & Bond's Dobby Classic Shirt ($69, Nordstrom), structured slacks, like this fitted ankle-length pair ($38, Calvin Klein), a brown belt, like Treasure & Bond's Oval Buckle Leather Belt ($49, Nordstrom), a multi-colored silk bandana, like Tory Burch's version ($78, Zappos), and cognac-colored flats, like Modcloth's Turn Back Prime Vegan Flat in Caramel ($39, ModCloth). To complete to look, top it off with a dash of Charlotte Tilbury's 'Amazing Grace' lipstick ($34, Sephora), named after the Princess of Monaco herself.