Gallery: The Worst Celebrity Summer Vacation Style Fails

Summer is officially here, which means you're hopefully able to take a vacation and get away from the rat race that is everyday life. While us normals are lucky to take a day off to head to the beach or lounge by the pool, celebrities are jetting off to exotic locations to sip on expensive-ass drinks and bask in a level of luxury that escapes 99% of the world.

You would think that the rich and the famous would be able to look decent at these various resorts and getaways. After all, it only takes a few good T-shirts, some reliable boardshorts, and a fresh cap to look good in the summer. Yet celebs are always failing at looking stylish while on vacation. Maybe they think that being slightly away from the cameras is an excuse to stop trying, but regardless, these are The Worst Celebrity Vacation Style Fails.

RELATED: The Worst Style Fails From the Most Stylish People
RELATED: The 10 Most Hilarious Celebrity Shopping Fails

Destination: France
When: 2009

Wearing a shirt that challenges you to "Check My $tats." Floral and butterly patterned capri pants with splayed drawstrings. Now that he's a two-time champ, hopefully LeBron can look back on this and slap his palm to his giant forehead.

Destination: St. Tropez
When: 2012

No matter where you jet off to in the world, a fedora will always give people multiple reasons to peg you as unstylish. Seacrest may be trying to keep the sun off his moneymaker, but surely there are other ways to do it than with the worst type of hat ever.

Destination: St. Bart's
When: 2012

While this photo is A. hilarious, and B. confusing, Diddy could definitely improve his beach steez a bit. That bathing suit is enormous, and combining black and white just makes you looke like a warm-weather penguin. Still though, that James Bond water-propulsion contraption thingy is sick. No idea what it is.

Destination: Malibu
When: 2012

Jared Leto clearly doesn't understand the point of vacation.

Destination: Hawaii
When: 2007

Matt Damon is pretending that he's having a fun time, but he's crying on the inside. If he only got some properly fitting shorts without enormously bulky cargo pockets, he could actually enjoy his time off.

Destination: Hawaii
When: 2011

If you're a celeb, dressing down while on vacay might dispel fans from swarming around you, but if you like a downtown Vegas coke dealer you might invite some unwelcome company.

Destination: Italy
When: 2009

We would expect more from Jake Gyllenhaal, but maybe being on vacation made him let his guard down. That's no excuse for a fedora and garbage sneakers to make their way into the picture, though. Now he just looks like dude trynna lurk on Reese Witherspoon.

Destination: Miami
When: 2012

This is the photo that shocked baseball fans into thinking that the Yankee captain had really let himself go in the off-season. While Jeter could maybe take some advice from big dudes, the first thing he needs to do is burn those disgusting cargo shorts.

Destination: Miami
When: 2013

This is what happens when the man who singularly embodies "Euro-trash" vacays in Miami. Shitty fedora (redundant), gross sunglasses, and bright pink fluorescent shorts deserve a red card, or at least to be mocked on an online platform.

Destination: Ibiza
When: 2008

You'd think that with a supermodel wife, Tom Brady wouldn't wear gigantic flared pants with a summertime beanie and scarf. But maybe that's the problem, after all.

Destination: Miami
When: 2012

While he was chillin' at the beach with now ex-girlfriend Karrueche Tran, Breezy was nearly attacked by a seagull. Maybe the bird confused Brown's ass with two hams. The singer really needs to pull up his pants/moral standards.

Destination: Anguilla
When: 2005

If you're going on vacation this summer, do the opposite of everything Hov's doing (except for the beer and the beautiful woman). He's definitely come a long way, and hopefully now knows all the reasons why men should never wear capri pants.