In Praise of Vacation Style

Because having the time of your life is universally flattering.

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Wish you were on vacation right now? We don't blame you. Vacation is awesome. It's one of the rare instances in life when you can do anything you want for an extended period of time—and that special kind of freedom is an occasion worth dressing up for.

But when you're on vacation, "dressing up" takes on new meaning. What are you dressing up for? A sunset sail? A hike to the top of a volcano? A leisurely afternoon by the pool?

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Whatever we're doing, we are almost always the happiest, purest versions of ourselves while on vacation, and that should manifest in the clothes we choose to wear.

Here are some of our favorite classic looks in the history of skipping town—plus some tips on how to incorporate them into your everyday life.

Margarita Chill

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In this photo, Tennesee Williams is technically working—he's on the set of the movie adaptation of his play The Night of the Iguana—but his style is fully acclimated to Key West's laidback, breezy vibes.

What You Need:

Straw Hat, $8,
Dobby Ticking Short-Sleeve Button-Down Shirt by CPO, $49,
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Nautical by Nature

In her crisp white top and high-waisted shorts, Lauren Bacall is a perfect match for her nautical environs. And Humphrey Bogart? He's working the sailboat look quite nicely himself.

What You Need:


Premium Linen Long Sleeve Shirt, $30,
High-Waisted Shorts by Emporio Armani, $234,
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Classic Navy Henley, $150,
Oxford Cloth Chino in 770 Fit, $78,

Flora, Fauna, and Fashion

Truth be told we do not know for sure that Diana Ross was on a trip when this photo was taken, but the vibe of the photo is pure vacation. We like to imagine she's just cleaned up after a long afternoon spent by the pool and is heading out to a romantic candlelit dinner on some exotic waterfront.

What You Need:

Henna Asymmetric Embroidered Silk Dress by Zimmerman, $850,
Long Earrings, $7,
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Australian Beach Party

When Mick Jagger took a break from a Rolling Stones tour to spend an afternoon at the beach, he also took a break from buttoning his shirt. The reason this works, apart from his being Mick Jagger, is the belt. It's keeping the entire look intentional.

What You Need:

Slim Irish Cotton-Linen Shirt in Nile Blue, $80,
Brown Cut-Edge Creased Belt by Levi's, $15,

Cute on the Cote D'Azur

In the '70s, Jane Birkin's sense of style was basically a permanent vacation, but of all the delightfully free-spirited photos of her, we like this one the best. She makes boating in heels seem almost worth it!

What You Need:

Boat Neck Ruffle Eyelet Blouse by Guild Prime, $141,
Le High Flared Jeans With Distressed Knee by Frame Denim, $125,

Moody Mallorca

In this picture, taken on a beach in Mallorca, New Wave film star Ana Karina's look is anything but typical beachwear. But that contrast is exactly what makes it so sexy. The smudged eyeliner doesn't hurt either.

What You Need:

Oversized Stripe Shirt Dress, $75,
Sport Waterproof Eyeliner, $20,

Venetian Holiday

Here, an engaged Jean Seberg and Romain Gary complete a perfect picture in their beautifully tailored attire. Kind of makes you wonder where that gondola is headed?

What You Need:


Long Wrap Dress by & Other Stories, $145,


Light Blazer in Anthracite Gray, $80,
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