9 of Your Fav Celebs’ Embarrassing First Magazine Covers

A lot of today’s hottest celebs have been in the business for at least a decade. Even the ones who are your age. 

Britney, Miley, Rihanna, Kim, Kylie, and the list could go on.    

While these days they all have their cover girl game on point, some of their earliest magazine covers are a little awkward.

Maybe it’s the pose, a ridiculous headline centimeters away from their thigh, or the nonsense they’re wearing, but something, if not everything, is off. 

Here are 9 examples of your favorite celeb’s embarrassing first magazine covers. 

1. Paris Hilton

2003, Seventeen 


2003 was a busy year for Paris. First, she graced the cover of Seventeen with her awkward puppy arms and tales of being a teen dwarf, then a few weeks later her sex tape was leaked, and three weeks later The Simple Life began airing.

Bet the good folks at Seventeen were really happy they chose Paris as their cover girl, right?

2. Kim Kardashian

2007, Complex


Complex meanwhile, went the other route with Kim. They deliberately sexed her up and had the audacity to ask, “Who is Kim Kardashian?”

3. Gisele

1998, British Vogue


Gisele’s first magazine cover is embarrassing for a different reason. Because she didn’t start off in some rinky dink magazine, she started off at VogueAnd she looked perfect.


4. Taylor Swift

2008, Blender 


What is this shirt? What is this pose? What is that facial expression? Girl, you really shouldn’t have.

5. Kylie Jenner

2012, Teen Vogue 


Remember back when magazines didn’t think that Kylie was enough of a star to have her own cover? LOL. How wrong Teen Vogue was.

6. Miley Cyrus

2006, Teen


LOL, Miley doesn’t even get referred to by name on her own cover!!!!!!! Sad.

7. Kendall Jenner

2011, American Cheerleader 


I think this one speaks for itself.

8. Selena Gomez

2008, Teen


Before Selena Gomez was the most followed person on Instagram, she was just Demi Lovato’s friend.  Oh, Teen Magazine. How gravely you underestimated today’s starlets.

9. Britney Spears

1999, Sky Magazine 


Gymslip? What does that word even mean, Sky Mag? And what are Sky People? And what did Jennifer Love Hewitt’s breasts do last summer?

In all seriousness though, RIP Sky Mag.

Too many questions, not enough time in the world to answer them.

Gimme More POP

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