slip skirt and long sleeve shirt outfit with ballet flats

What I Would Wear As Audrey Hepburn in the 21st Century (the Best Audrey Hepburn Outfits Recreated)

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Audrey Hepburn is arguably the greatest fashion icon. From casual pieces like oversized white shirts and black tops to her enviable glam red carpet dresses designed by Hubert De Givenchy, no matter what she wore, Audrey Hepburn embodied a timeless elegance. Her style legacy continues to live on decades later and has had a great influence on everyone’s fashion taste – including mine. To celebrate her legacy, I have recreated some of the best Audrey Hepburn outfits – but with a 21st-century twist! Instead of copying the exact pieces she wore in the photos, I captured the essence of her style. Keep scrolling to see how I put everything together from a 2023 lens!

1. long sleeve shirt + midi skirt + ballet flats

Okay, so if this is what you wear golfing, I would have tried this sport years ago! I think we can all agree that this is the best golf outfit – very classic and chic.

Voluminous skirts and ballet flats defined Audrey Hepburn’s style. She often teamed up her skirts with a stylish and timeless waist belt to cinch in her waist. Her choice of footwear was usually ballet flats due to her love for dance and her background in ballet.

Fun fact: She always told the press that her dream career was to become a ballet dancer. Audrey wore ballet flats so often that they are now just associated with her, even if she didn’t create them. The actress also invested in a lot of classic wardrobe basics like this black long-sleeve top.

top | skirt (similar) | flats (similar)

I love this look so much that I had to recreate it – but with a 2023 update. To start, I wore a similar black top to capture the Audrey Hepburn look. However, instead of teaming it up with a yellow voluminous skirt, I opted for a slip skirt for a modern touch. No Audrey Hepburn-inspired outfit is complete without ballet flats, so I slipped on a pair to nail her look.

2. boatneck dress + layer + flats

Audrey Hepburn certainly knew how to piece together a beautiful outfit. With this look, the actress proved that simple outfits can be fun, yet unique and classic too.

Instead of wearing a boatneck dress on its own, she layered it over a black long-sleeve top for some coverage and an elegant finish.

dress | blazer | flats (similar)

I followed her style notes by pairing an extra layer with my sophisticated dress. Though the long sleeve shirt underneath is a great styling idea, I’m more likely to pair something over my dress in 2023.

However, by choosing navy to wear with black, it does add an element of an unexpected style choice, similar to Audrey’s look. The blazer was a great choice as it’s also a piece that Hepburn loved wearing regularly – though hers was more of a lady tweed jacket. And of course, to finish my Audrey Hepburn-inspired look, I completed it with ballet flats.

3. button down + midi skirt + flats

I think we can all agree that Audrey Hepburn had an impeccable sense of style! I mean, look at this outfit. It is so timeless that you’d think it’s from a 2023 J.Crew AD.

For this outfit, the actress was pictured wearing three of her signature pieces: a button-down shirt, skirt, and ballet flats.

skirt | flats (similar) | button-down (similar)

This look was calling my name and I had to recreate it. However, I made some tiny changes. First, the top. Instead of going for a wrap-style printed button-down shirt, I went for a crisp white design.

The skirt is also quite different from hers. I decided to dress up in a midi slip skirt instead of a maxi pleated skirt for a more modern touch. But of course, no outfit is complete without ballet flats!

Related: Classic Style Tips to Steal from Audrey Hepburn’s Outfits | Recreating 5 Timeless Looks

4. trench coat + boots

In another chic style moment, Audrey looked effortlessly elegant in a trench coat and boots. Wearing a trench coat is never not a good idea, which is why I had to copy this look, obviously!

A trench coat is still an effortless piece to wear today and knotting the belt on the coat is a simple style statement to make.

trench coat (similar) | boots

Though we can’t see what she was wearing (though it was probably flats) I paired the coat with knee-high boots for a sophisticated finish and a 2023 update. Taller boots paired with a longer coat also give the illusion of the trench coat being a dress!

5. dress pants + loafers + trench coat + scarf

Hepburn never shied away from wearing menswear pieces like loafers. She showed that women can look classy in penny loafers and dress pants without losing their feminine touch. She also showed how to add feminine touches to these menswear pieces, such as a silk scarf.

trench coat (similar) | pants | loafers

In this outfit, she wore a trench coat and dress pants which resulted in a feminine and sophisticated look. I recreated the look while giving it a few tweaks. Instead of accessorizing the outfit with a scarf around my head, I opted for a scarf tied around my neck paired with a pendant necklace.

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I’m a big believer that improving your style doesn’t always mean buying new clothes. Sometimes it means finding the right inspiration to copy to use what you have!

Dress up like more stylish icons by checking this next post. Up Next: 6 Ways to Dress Like a Classic Hollywood Actress on Your Summer Vacation

The best Audrey Hepburn outfits


Founder and editor of My Chic Obsession, Carolyn is your trusted fashion maven. Carolyn's drive to help others achieve a classic and timeless wardrobe fuels her posts, making a go-to resource for style seekers worldwide. Beyond the wardrobe, she resides in the heartland of the Midwest, dreaming up new ideas and raising her two lively boys - her biggest fashion critics.