Celebrity Street Style on Vacation!

How do Hollywood's finest take their looks from the city streets to the beach? We took a look at our favorite style-setters to see how they make the summertime switch.

By Kate Schweitzer

July 12, 2011 11:45 AM
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Jackson Lee/Splash News (left); Splash News (right)
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Beyonce Knowles

The singer loves to mix conservative pieces — like a pink tweed jacket — with edgy accessories and short shorts while hitting the theater district in New York City, and when she and hubby Jay-Z deboard their yacht on vacations to Saint Tropez, her style is just as eclectic.
gwen stefani
Gotcha Images/Splash News (left); KCSPresse/Splash News (right)
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Gwen Stefani

The L.A.M.B. fashion designer barely shows any skin (save for that sheer black top) while out for a walk in London, but when she's boating through Cannes, France, she reveals the abs that made her famous in a wild animal print bikini set.
kristen bell
Santi/Splash News (left); Starsurf/Splash News (right)
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Kristen Bell

The actress does a fine job blending in. In New York City, she stays on trend without trying anything too crazy, and she lays low in Hawaii in a basic teal suit with (gasp!) reading glasses! Best disguise ever.
katie holmes
Jackson Lee/Splash News (left); Ralph Notaro/Splash News (right)
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Katie Holmes

Mrs. Tom Cruise is one of the few A-listers who seems to spend more time getting dressed for the pool than the paparazzi. Normally relaxed in jeans and oversized cardigans, while in Miami, the actress went full-on Jackie O in an oversized sunhat, classic one-piece suit, and long coverup.
Splash News (left); Derek Shook/Splash News (right)
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Busy Phillips

Like her Cougar Town character, the actress is all about fun, flirty colors that pop, whether she's out and about in California or taking a break from filming in Hawaii.
SM/Splash News (left); Splash News (right)
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Drew Barrymore

Known for her hippie-bohemian street style, she doesn't disappoint when she arrives decked out in fringe in London. Her trademark look gets pared down, however, when she braves the waves in basic black near her home in Hawaii's Kauai island.
Pete Goddard/Splash News (left); Pichichi/Splash News (right)
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Katy Perry

There's nothing casual about the pop star's street style, and this bubble dress, Angora sweater, and cat-eye glasses combo make it clear. She even sticks to her guns on vacation — ruffled pink bikini and sparkly headband and all.
Santi/Splash News (left); Splash News (right)
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Christina Aguilera

No matter where she is — from the streets of New York to poolside in Miami — Xtina always brings a hat … and some bright red lipstick.
KCSPresse/Splash News (left); Steve Dennett/Splash News (right)
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Fergie

Ever the urban dresser, the Black Eyed Peas singer loves to head out in a mix of textures, never without some black leather thrown in. But on vacay, she loosens up for some much-needed R&R in one of her favorite summer must-haves: the romper.
JosiahW/Splash News (left); Splash News (right)
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Heidi Klum

While out with her kids Henry and Leni, the Project Runway host sticks to skinny jeans and sneakers, but when on vacation with her family on their yacht in Portofino, Italy, the supermodel sticks to what she wears best: next to nothing.
Jackson Lee/Splash News (left); Clasos.com/Splash News (right)
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Jennifer Aniston

It's hard to look more relaxed that Ms. Aniston. No matter where she goes, her trademark tanks and mix-and-match bikinis — all in neutral tones! — never, ever fail her.
Richie Buxo/Splash News (left); Piko Press/Splash News (right)
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Kate Hudson

Pregnancy certainly agrees with Kate! Whether she's heading to a talk show taping in sky-high heels or browsing the local outdoor markets in Buenos Aires, her diaphanous frocks keep her looking (and likely feeling) cool.
Splash News (left); Fred Montana/Splash News (right)
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Ciara

The songstress shows her sexiest assets wherever she goes: her toned legs while listening to music in Beverly Hills and her sleek abs while toweling off beachside in Miami.
MBD/Splash News (left); KCSPresse/Splash News (right)
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Halle Berry

The Oscar winner has California casual down, whether she's in a tee and jeans number in L.A. or hitting the beach in Malibu in a revealing tank and shorts.
Wenzelberg/Splash News (left); Clint Brewer/Splash News (right)
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Cameron Diaz

It's not easy to look this effortlessly chic while running errands or running through the sand, but the star knows the Hollywood dress code for such endeavors: lightweight layers and a must-have accessory (like her oversized tote and that blue-rimmed fedora).
Richie Buxo/Splash News (left); Splash News (right)
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Kate Bosworth

The actress goes feminine while out in New York City but gets serious (à la her Blue Crush alter ego) in a sporty bikini and head wrap in Hawaii.
Capo/Splash News (left); Fred Montana/Splash News (right)
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Kim Kardashian

No self-respecting Kardashian would be caught dead hitting the streets without a full face of makeup, a fresh blowout … and a Birkin bag. So, it's no wonder the reality star always looks perfectly put together, whether she's on a break from filming her E! show or enjoying the sun in Miami.
Splash News (left); Carl's Jr./Splash News (right)
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Olivia Munn

It's hard to handle leather pants on the steamy streets of New York City, but the comedian seems just as comfortable in them as she does on the back of a jet ski.
Jackson Lee/Splash News (left); Splash News (right)
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Rihanna

The singer loves to experiment. At times, she goes ultra-feminine, as she does out and about in New York City. But she also knows how to have fun. Case in point: While on vacation in her native Barbados, she wore a swimsuit with a very-well-positioned tiger face.
Splash News (left); Pichichi-Garces/Splash News (right)
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Nicole Richie

The reality star-turned-designer never strays far from her boho sensibilities. In fact, her maxi-dress-filled-closet works double-time for her both in the city and on the beach.
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