Fashion
Jessica Simpson: This Is How She Rolls

Double-belted into her mom jeans, former pop singer/reality TV star turned attempted country crooner Jessica Simpson appeared at some sort of chili cook-off concert in Florida this weekend.

Jessica Simpson
It is unclear if she was there to perform or just judge.

UPDATE: Thanks to the folks at WKIS, there is footage of Jess performing "These Boots Are Made for Walking" at the cook-off -- and lets just say, it takes your mind right back to the days she rocked out to the same song in that extremely tiny red bikini...

Jessica Simpson: Click to watch



Tags: chili cook-off, ChiliCook-off, Florida, high waisted jeans, high waisted pants, HighWaistedJeans, HighWaistedPants, Jessica Simpson, JessicaSimpson, mom jeans, MomJeans, performance

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(Page 4 of 32) Previous 15 Comments | 2 | 3 | 4 | 5 | 6 | Most Recent | Next 15 Comments

46. This is such an unflattering picture, but I think that the angle that it's taken from is probably partly to blame. A shot taken from ground-level looking up is really not going to make a great picture of anyone. Still, those pants are absolutely wretched, no matter what angle.

Posted at 10:44AM on Jan 26th 2009 by Canajun, Eh!

47. Never saw her look better. Bravo!!

Posted at 10:44AM on Jan 26th 2009 by artie help

48. I keep Refreshing my Computer, but it doesnt help..
She still looks like a Lard Ass..

Posted at 10:46AM on Jan 26th 2009 by Neorules2112

49. All she needs is a Budweiser and a cigarette and she could be from my home town.

Posted at 10:52AM on Jan 26th 2009 by jules

50. yep! Definitely a MISS in wardrobe choice! Thinking that I almost went there just to have a chance to see her live. Can't say I regret not to. How disappointing!
But how fast are we, people, to shoot her down just because of a poor choice of clothes and maybe a few pounds gained!
Sad!

Posted at 11:00AM on Jan 26th 2009 by frenchinmiami

51. After seeing this picture I'm worried! Worried that Jessica is going to wait too long until she's really out of her prime and then start posing naked. I wanted to see here nude last year, not next year.

Posted at 12:03PM on Jan 26th 2009 by MrMike

52. THAT OUTFIT IS RIDICULOUS BUT SHE SURE THINKS SHE'S ALL THAT.

Posted at 11:11AM on Jan 26th 2009 by PENNY

53. LOOKS LIKE EITHER IT'S HOLDING IN HER FAT STOMACH OR SHE JUST WON THE WWF TITLE......WHAT WAS SHE THINKING.

Posted at 11:11AM on Jan 26th 2009 by PENNY

54. I was there as were 35,000 other people. From my seat all you saw was blonde hair. She talked between every song and and sang well. (not a fan). The sound was lost during her last song. Nobody in the crowd heard her just the band. They played to the end and probably wondered why no one was paying attention or applauding. Most the crap she received was talking about her boyfriend.

Posted at 11:01AM on Jan 26th 2009 by dan

55. She sang at the Chili Cookoff in Florida, it is a country music concert where Alan Jackson headlined it. Jessica was HORRIBLE, she isn't a good singer and should never have tried to cross over to the country side. She is a total ding bat. At one point the sound went off and she didn't even know and kept on singing even though no one could hear.

She needs to find a new career cause singing isn't getting it!

Posted at 11:04AM on Jan 26th 2009 by Laura

56. It's a linebacker in mom jeans.

She has the most unfortunate shape. Where is her waist?

Posted at 11:04AM on Jan 26th 2009 by plus sized

57. Holy Hanna!!! Does she really think she is sexy?? She needs to marry Tony Romo and retire.....FAST!!

Posted at 11:09AM on Jan 26th 2009 by Christy

58. It's Anna Nicole Smith!!

Posted at 11:10AM on Jan 26th 2009 by Mayla

59. She looks like she has started a nice little GUNT.

Posted at 11:12AM on Jan 26th 2009 by Choppy McSlut

60. Did Romo confess a crush he had on Anna Nicole Smith? Is Jessica desperately trying to hang on to him by doing her best Anna Nicole impersonation? Wow, she is a big girl...

Posted at 11:12AM on Jan 26th 2009 by anonymous

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