Jessica Simpson wears short shorts

August 14th, 2006 // 105 Comments

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Jessica Simpson performed at The Factory last Friday and wore some shorts which showed off her lower butt cheeks. Which would’ve been fantastic two years ago but now she just looks dated and desperate. And that front pouch she’s got going on doesn’t help at all. It looks like she’s hiding a diaper under there. And those shorts look like something a 50-year-old woman would wear if she was asked to dress like a protistute from the early 90′s. This comes to mind.

More of Jessica and her neat shorts after the jump.


  1. JoBOO

    FIRST — and I’d hit that three times — once in each hole!!!!

  2. MR_DG


  3. the one word that comes to mind when looking at her is “weathered”

  4. diamondprynzez

    Too bad… she probably put that on and thought ‘Nick will get jealous’

  5. Equalparts

    The most boring woman alive. She looks like a dwarf. The fact that this woman is a star is only proof at how freakin’ bored as a society we are. Who is convincing her that these outfits are flattering?

  6. BarbadoSlim

    Who wears mom-shorts?

    She wears mom-shorts…

    I know daddy likes’em!!

  7. plymouthrock

    on pic #4 is that sweat coming out of her ass?

  8. Hey Superfish guy, what’s a “protistute”

    You should have given us this story to rag on:

  9. Carolicious

    Meh. At least she looks healthier then some people, ahem, Nicole Richie. She’s got meat, good for her!

  10. gatorbates

    I’d hit it up … I’d hit it down … I’d hit hanging from the ceiling fan, or with a toaster involved. I’d hit it any which way I could.

  11. PunjabPete

    Pouch? She is WAY to young to already have a frass. (front ass)

    Looks like shizzle. Yo.

  12. gatorbates

    Is that MEAT hanging out in picture # 7?

    I’d swallow that roast beef.

  13. So tired of her. Shouldn’t she be like, a D-list celeb by now?

  14. ScriptRadar

    Still sexy.

  15. reenie11

    maybe if she would quit hanging out with FAGS she could get laid again. Doesn’t she have any female friends? It seems that the only people around her are paid to be there. But I guess thats what happens when you are as entertaining as she is. Where’s Daddy Joe?

  16. docta

    oh please. jessica simpson has a great, womanly body. it shocks me how people prefer nichole richie over jessica simpson.

  17. ImSuicidal

    If she had a “third” breast on back and she’d be the perfect woman.

    For dancing!!!!!

  18. LL

    You’d have an easier time convincing people Jessica’s fat if you didn’t follow her immediately with the frightening skeleton that is now Nicole Richie. Jessica looks OK, just not quite as fit as she has in the past. Clearly, she’s not been keeping up with that “Dukes of Hazzard”/daisy dukes exercise regimen. But wouldn’t you rather gaze at her than Nicole? Damn… big asses beat bony ones any day of the week.

    Having said that, the shorts are not flattering (and shorts with heels are never cool, no matter what anyone says). She’s wearing the shorts because the fashion powers that be are trying to force all of us into short shorts and “skinny jeans” so that anyone with an ass wider than Nicole’s will look like a heifer. Mission accomplished!

  19. She still around?

  20. RichPort

    She’s wearing that belt because Nick told her it has her first initial on it.

  21. Who was the cameraman on #4, Verne Troyer?

  22. Alacran

    I agree #18, Nicole is Nasty, I’d rather see Jessica Simpson wearing a Mom Jean than what I just saw from Nicole. But I would really love to see Jessica Alba or Scarlett Johanson on a bikini again, summer’s only halfway there, there’s still hope….

  23. DancingQueen

    Is that a nip slip in the last picture? I think she’s a cute, albeit stupid, girl, but man what a horrid outfit.

  24. BitchyMcBitch

    NOBODY should wear short shorts. Unles your under twenty and work out regularly. You really shouldn’t bother. I’m not being funny but her hairdresser goes with her everywhere. What is she unable to cross the street without having her hair touched up?

  25. Her continued hanging around with her cockloving hair dresser really sends out some bad vibes if she’s trying to get laid again. Any certifiably straight guy, and granted in Hollywood that’s asking alot, would not spend the night being cockblocked by a fag. There’s a certain amount of dignity involved. You can picture the aforementioned hairdresser, intoxicated and horny, saying to any possible suitor of Jessica, “I can suck you longer than she can, big boy. And I make a mean latte in the morning!” How is one to respond to that? Poor Jess, she collects faggots like Lindsay collects STDs.

  26. rlt

    #11, it’s not a frass. (front ass)

    It’s a straight up FUPA (Fat Upper Pussy Area). Those shorts just scream it. Ugh!

  27. reenie11 here’s something other than Hohan, simpleson or the grim reaper.

  28. The Hoff

    #10 yup, I’d make it water-tight

  29. KristinMichelle

    That’s rather unfortunate to wear shorts up to your ass cheeks, four inch heels and your legs STILL look stumpy. I have always sworn that this woman was born with some sort of achrondroplasia. Nothing gets more ridiculous than having your hair stylist follow you to brush the bangs out of your eyes. The worst part about her is the “Come see how good I look!” expression she always sports… What a hag.

  30. Tracie

    I agree that she’s got to stop hanging around with Ken Paves as a friend and actually let him do his job – which is supposed to be a HAIRDRESSER. Jessica’s hair looks like crap, the outfit is most unbecoming (and polyester?!), and can you image how long it took her in the loo? You have to take the entire stupid outfit off to pee! (Although #7, that may explain your question.)

  31. MicShell

    Could be a nip slip in the last picture. picture #7 is that a lab hanging out?!

    what exactly is going on in the car behind her? Is that an amputee on the floor or what?

    Ya’d think with so much time spent with her hairdresser – that her hair would look better.

  32. krisdylee

    And now I shall play the devil’s advocate…

    Perhaps Jessica tragically lost all her mirrors to a mirror thief. Or perhaps, Jessica’s minions grouped together for some kind of practical joke, telling her “Yeah, girl, those shorts are so hot… you look fan-fucking-tastic… Nick will DEFINITELY be crying in his beer tonight…”

  33. ImSuicidal

    achondroplasia – a-c-h-o-n-d-r-o-p-l-a-s-i-a – achondroplasia

  34. purplepuppy

    What’s with the waistband being jacked up to her chin. Could you wear you pants any higher, Jess? You should, it’s a great look….old men have been doing it for years, and they are the most fashionable people on the planet. FUCK I HATE YOU SO MUCH!!! I want to scratch her face off!

  35. andrewthezeppo

    I’m sick of pretending reality TV stars are celebrities…I guess she kinda has music, and kinda made a terrible movie….but come on she’s only famous for her boring show about her crappy marriage to a man that clearly loathed every word that came out of her mouth.

    no more Paris, Nicole, Jessica or worst of all those Laguna Beach skanks…they’re boring talentless and all wear the same stupid clothes because they have the same stupid stylist…Rachel Zoe who Allure said single handedly brought back annorexia.

  36. PunjabPete

    15 – After the trauma that Joe inflicted, is there really any surprise?

  37. diptutod

    You know, for a thin woman she sure knows how to make herself look fat.

  38. Jacq

    She’s got a Paris Hilton-style ass-flap happening.
    So now that she’s divorced, she’s a professional fag-hag?

  39. oshkoshb-goshdammgosh

    Do you think she can shake it like a polaroid picture?

  40. Great body, not the best outfit. It reminds me of the Olivia Newton John outfit in Grease but with the legs cut off way too high. She looks like she needs a cat whip with that out fit.

  41. DMB in da ATL

    Maybe she thinks if she shows a little ass cheek, no one will notice how FLAT her ass is…

  42. cobra

    Is that Pam Anderson or Anna Nicole Smith?

  43. Bambib9

    Jessica has seen better days, she has a curvy womanly body, and great boobs! However, I can NOT stand this new trend of short ass-revealing shorts, along with the Mischa Barton favorite – the skinny jean! Those should only be worn with boots over them not with ballet slippers…and don’t get me started on those…

  44. BarbadoSlim

    As old man Jenkins would say: “them’s some nifty fitting pants girlie”

    hahahaha, any unfortunate suitors have to unbutton and lower her pants to get some tit action going.

    And don’t even get me started on the Papa Joe’s sloppy seconds situation.

  45. diddleysquat

    She has the ass of a 50 year-old…She’s gotta work on that sh*t.

  46. katydid

    In totally unrelated news (except both women are blond) – Kate Hudson and her husband have split.

    Publicist Brad Cafarelli confirmed that Hudson, 27, and Robinson, 39, had split. He offered no details. The couple, who were married on New Year’s Eve in 2000, have a 2-year-old son, Ryder.

    A spokesman for Robinson said he had no comment on news of the separation, which was first reported by People magazine on its Web site.

  47. Italian Stallion


    Shake it, shake, shake it, shake it (OHH OH)
    Shake it, shake it, shake, shake it, shake it, shake it (OHH OH)
    Shake it, shake it like a Polaroid Picture, shake it, shake it
    Shh you got to, shake it, shh shake it, shake it, got to shake it shake it like a Poloroid Picture

  48. ToiletDuck

    What a fucking prostitute…

  49. IzzyInATizzy

    Re: #12 & #31:

    BUTT-FLAP/DANGLING-LABIA ALERT CONFIRMED in the 7th picture. It’s amazing how much I’ve learned about anatomy by looking at photos of inappropriately dressed celebs– or rather, how confused I’ve become, because this excess-flesh-in-the-female-groin thing it getting weird (like all those creepy pictures of Paris Hilton).

    Maybe these girls are such hos, their genitalia is getting really loose and just sort of falling off the bone at this point. Isn’t that called leprosy or something?

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