Little black dress
The sleek black number designed by Hubert de Givenchy for the opening scene of the 1961 romantic comedy Breakfast at Tiffany’s, is often referred to as the most famous ‘little black dress’ of all time. Greeshma Thampi, an image consultant, recommends choosing a silhouette that compliments your body shape. “The right dress will have a classic silhouette and be comfortable. An A-line style works well with pear-shaped bodies, while shift dresses are more forgiving to your mid-section. Pair your dress with a string of pearls and a beehive for a look that is understated and yet glamorous,” she advises. 

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White shirt and circle skirt
In 1952, Hepburn was cast as Princess Ann in A Roman Holiday, where Edith Head designed her wardrobe. The outcome was the timeless combination of a white shirt and coloured circle skirt, which Hepburn wore on the streets of Rome.

As the film progressed, she rolled up the sleeves of her shirt, adding a casual edge to the classic look. Design student Vinanti Jain recommends knotting the shirt at the waist for a more cinched silhouette and adding a hair band, another regular feature of Hepburn’s on- and off-screen looks. You could also knot a scarf around your neck to accentuate the laidback-chic vibe. 

Shorts with plaid shirt
Simple white shorts with a plaid shirt and wedges are as chic and comfortable today as they were when Hepburn wore them with such élan. To replicate this look, choose a pair of high waist shorts, says Jain, and tuck a breezy, long-sleeved shirt in to highlight your waist.

For a more feminine flair, pick a pair of shorts with lace embellishments. Complete your outfit with wedges or slides, and retro cat-eye sunglasses. If you aren’t a fan of shirts, a top with horizontal stripes and a relaxed fit works well with this look. You could also swap your wedges with delicate strappy sandals. 

Black turtleneck with cropped pants
The 1957 musical Funny Face saw Hepburn perform a Bohemian-style solo dance at a nightclub dressed in a plain black turtleneck sweater and black cropped pants with black penny loafers. This outfit, says Jain, ticks the right boxes in terms of comfort and style, especially with the current nip in the air.

“A black turtleneck sweater is very versatile and hence a good investment piece,” she adds. Alternately, ballet flats work well with this combination, as do a beret or a scarf. Add a pop of colour with your footwear and accessories, to add more dimension.