Dress Like An Icon: Audrey Hepburn in 'Roman Holiday'

Learn how to dress like Princess Ann in the 1953 film

Updated on 10/30/17

Every time I watch "Roman Holiday," I'm in awe of Audrey Hepburn's teeny-tiny waist and perfect gamine features. But I'm also in love with Hepburn's classic when-in-Rome ensemble, complete with a charming scarf, white shirt and circle skirt.

It's the perfect outfit for Hepburn to wear as Ann, a stifled princess who runs away to explore the Eternal City on her own. In the romantic comedy (released on August 27, 1953), Gregory Peck plays a local reporter who helps Ann, but secretly wants to break the princess' big runaway story. But of course, a lovely romance brews. The film raked in three Academy Awards: Best Writing, Hepburn for Best Actress and the legendary Edith Head for Best Costume Design, surely for Hepburn's iconic, romantic outfit that makes you want to eat gelato on the Spanish Steps.

The next time you tour Rome, or your own hometown, add a little "Roman Holiday" style to your outfit with these timeless pieces.

01

of 06

The White Shirt

Audrey Hepburn And Gregory Peck In 'Roman Holiday' — Archive Photos / Stringer / Moviepix / Getty Images

This is the ultimate white button-down shirt because it’s fitted and has an open v-neck collar that shows off a bit of décolletage. It’s both adorable and put-together, even with the rolled-up sleeves. Hepburn wore many collared shirts like this in her everyday life paired with Capri pants and high-waisted shorts. You’ll get years out of a versatile shirt like this.

Tip: Splurge on a white shirt that’s high quality and fits you to a tee.

02

of 06

The Scarf

Audrey Hepburn, "Roman Holiday," Copyright Paramount Pictures

If you ride around on a Vespa, or just ride around town in your car, a scarf will protect your neck and add a little 1950s flair to your white shirt. This striped scarf on Hepburn is simple yet chic. Go for a small scarf that’s around 16 ½" square.

Tip: Save a little money and find a great vintage scarf at a garage sale, thrift store or in your grandma’s attic.

03

of 06

The Skirt

Eddie Albert, Audrey Hepburn and Gregory Peck, "Roman Holiday" Copyright Paramount Pictures

The circle skirt is the epitome of mid-century femininity. When it’s cinched at the midsection with a belt, like on Hepburn’s enviable waist, this silhouette is demure yet alluring. If you have a shorter frame, opt for a skirt that hits just above or just below the knee. A midi-length skirt can overwhelm a petite frame or look matronly.

Tip: Watch out for pleated circle skirts. They can add girth even to the slightest of frames.

04

of 06

The Sandals

"Roman Holiday" Copyright Paramount Pictures

Strappy, gladiatorish sandals like these add instant Italian flair. If you’re gallivanting through Rome’s piazzas or just headed to the local supermarket, sandals keep the ensemble casual yet sophisticated. But whatever you do, never wear flip-flops with this look. Flip-flops are not strappy sandals. If you need extra comfort, try a simple ballerina flat.

Tip: Like a little height? Try a low-wedged espadrille sandal.

05

of 06

The Hair

Paolo Carlini and Audrey Hepburn, "Roman Holiday" Copyright Paramount Pictures

In this famous scene, Hepburn’s Princess Ann decides to chop her lovely long locks into a trendy Italian haircut that her friendly barber (played by Paolo Carlini) says is “cool.” Not everyone can pull off a pixie cut like Hepburn, but the idea is to keep your hair off your face. If you have long hair, throw it up in a youthful ponytail or in a messy updo (nothing severe or overworked). If you have medium-length locks, push your hair back with a headband. Keep the hair clean, fresh and youthful.

Tip: If you do get a pixie cut, keep it choppy and a little messy. Bangs can be jagged.

06

of 06

The Makeup

Hepburn was such a gorgeous gal that she didn’t need a whole lot of makeup. To get this doe-eyed gamine look, keep the skin dewy and natural and accentuate the eyes. Line the upper lids with black eyeliner, leaving the lower lashes clean. Curl lashes with an eyelash curler and apply black mascara. Leave eyebrows thick and fill them in with a brow pencil. Finish it off with a pop of cherry red lipstick.

Tip: Remember, less is more. Focus on the eyes and lips.

Keep up with the latest vintage clothing news on Twitter @trendyjenny, Facebook, Pinterest, and Instagram