6 Audrey Hepburn Outfits That Still Feel So Timeless

You've got actors, and then you have movie stars whose work makes us feel all the feels, transcends generations, and gets embedded into the cultural zeitgeist. Add in the dreaminess of Old Hollywood, and we couldn't be talking about anyone else but Audrey Hepburn. Still today, the Belgium-born actor is immediately recognizable courtesy of those big brown eyes, that sporty little pixie cut, and her sparkling, sophisticated charm. Hepburn started racking up credits in the early 1950s, scoring her breakout role in 1953's "Roman Holiday," which earned her a best actress Academy Award — and she'd keep working for nearly four decades. But her work isn't the only reason why she's such a legendary figure. There's also her fashion.

Beyond the work, Hepburn remains one of those pop culture style icons you should let influence your wardrobe. You could get lost for hours going through her old photographs, and notice that there's no shortage of iconic outfits in her wardrobe. Her best looks have withstood shifting trends no matter how much time has passed. No one would bat an eyelash if a stylish gal in the 2020s pulled on the checker print cigarette pants Hepburn wore in 1955 or the jewel-toned pink gown she wore to the 1992 Oscars. 

In the 1950s, Audrey Hepburn posed for glamour shots — as she was known to do here and there — leaning against a tree and draped in a simply chic outfit that could work in any era. The "Funny Face" star was rocking a dark lip and her signature micro bangs, wearing a long-sleeved blouse that was wrapped and tied tight at the waist. She paired the top with a classic tea-length black shirt and popped on a pair of easy ballet flats that haven't gone anywhere in the decades since.

Around 1955, photographers snapped pics of Audrey Hepburn and her first husband, actor and director Mel Ferrer, horsing around in an Italian vineyard. The two were married the year before and would stay together until 1968. As for the look, Hepburn wore a sleeveless cream-colored turtleneck that's still a closet staple all these years later. Opposite the top, the "My Fair Lady" star reached for a pair of cropped cigarette pants, stamped with a playful red-and-white print that recalled a picnic tablecloth, perfect for an afternoon in the Tuscan sun.

Audrey Hepburn won the best actress Oscar for "Roman Holiday" at the 26th annual Academy Awards, and the day after, the actor sat for a press conference in New York City in 1954 dressed demurely in a skirt suit. The outfit perfectly struck that balance between stylish and professional. Between the dark gray color and the razor-sharp jacket with its snappy collar, Hepburn looked ready to accept compliments and answer questions about receiving Hollywood's greatest acting honor. Today and forever, the midi skirt suit is the trendy alternative to buttoned-up workwear.

In March 1992, Audrey Hepburn attended the 64th annual Academy Awards in Los Angeles, snapped here with Jack Valenti, the longtime head of the Motion Picture Association of America. The "Breakfast at Tiffany's" actor popped loudly in a one-shoulder fuchsia gown crafted from an opaque silk organza-type fabric. She stole the show in the dress, which featured elegant draping at the bodice and a long cape sleeve. Hepburn died a year later, in 1993, at home in Switzerland surrounded by friends and family.

If you're rounding up the celebs who made major fashion statements with hats, go ahead and add the outfit Audrey Hepburn wore in 1958 to your list of favorites. The "The Nun's Story" star was captured collecting foliage in a forest in Congo while donning a two-piece 'fit that was equal parts charming, ageless, and versatile. We could easily see a low-key gal rocking Hepburn's lavender gingham print tank top and matching maxi skirt in any decade. The ribbon-wrapped sun hat really underlined the point.

Audrey Hepburn showed up to the 26th annual Academy Awards in New York City in 1954 to accept her best actress trophy dressed in a classically cut gown that'll go down in history as one of the most unforgettable — and timeless — looks in the Oscars ever. The white fit-and-flare dress offered a simple, time-honored silhouette and was decorated in a dreamy floral print that has yet to go out of fashion. The belted, tea-length Givenchy gown sold at auction in 2011 for £84,000. That's the 2020s equivalent of over $170,000.