Debra Messing knows how to dress

September 19th, 2007 // 111 Comments

Debra Messing was spotted shopping around Los Angeles wearing whatever the hell you would call this. Clearly “dress” isn’t the proper word here. I’m not even sure if “clothes” fits. This is what you’d get if you pulled a blind man out of the jungle and asked him to design a dress, keeping in mind that he has no idea what a dress is and also he’s blind. She could be wearing a vacuum cleaner on her head and she’d look less ridiculous.


  1. Zoey Lund


  2. Jessy

    L O L

  3. Ramiro


  4. Turtle

    I love a parade and the clowns.

  5. ive heard of peeps wearing parachute pants – but not actuall parachutes!



    ~ 420 ~

  6. nicolaz

    Jewish Tasteless Cow

  7. Zoey Lund





  8. asfasfdfdasdsaf


  9. Zoey Lund



  10. hill

    Oh lord, I think she mistook BOHO for HOBO…. nice try anyway. Or maybe she borrowed some clothes from Rosie O’Donnell?

  11. she is so irritating.shes not pretty and acts fake.

  12. Lexoka

    I think this is a djellabah… or maybe some kind of experimental sleeping bag.
    Who is she, by the way?


    It looks like a carnival tent…. or a big ass balloon that’s deflating!!

  14. Britney Crotch Juice

    suppose Express is happy to have their name right next to…well…that…um…thing?

  15. Ben Gay


  16. bigSTEAMYone

    WHAT THE F-CK IS THAT !!, …looks like a deflating hot air ballon .

  17. AddictedtoPixels

    #6 – While I agree she looks like a complete moron and has the fashion sense of a lobotomized chicken, I’m having trouble figuring out what her being Jewish has to do with anything. Oh right, it doesn’t, you’re just a racist asshole.

  18. Is she going on a pilgramage?

  19. Zoey Lund


    SHe’s got quite the Von Stapp look going there.

    (Google it, kids)

  20. cowgirl cow tipping

    Is that a “moo moo”?Hehe. I crack my OWN shit up!

  21. Lexoka

    #20 To where? The Shrine of Unholy Bad Taste?

  22. LL

    It’s one of those things they put over your house when they’re spraying for termites. Maybe she’s being fumigated.

  23. Cowgirl

    Funny! LMFAO at that one 23!

  24. no1justminda

    whaaaaaaaaaaaat? that’s some funny shiat

  25. FagHag

    Yes, fumigating her hot, wet, nasty pussy.

  26. combustion8

    man wtf happened to her? she was so hot in 2000.. now just 7 years later shes a friggin train wreck.

  27. G

    She sure seems to be caught in the most horrendous outfits recently. She’s probably still attractive under the tent.

  28. Coroner

    I hate it when they re-animate.

  29. anonymousryan

    Debra Messing: newest member of the Polyphonic Spree.

  30. gross

    she is an ugly chick that puts a ton of makeup on to make herself look tolerable at best. she also has a stick body with no tits at all…she does have surprisingly nice feet (from another pic) which is about all i can say nice about her. i bet her outfit cost $1500. i wonder if the rug matches the drapes…?

  31. lambman

    Weird, she looked so hot at the Emmy’s and that was like 2 days ago.

    31- Carpet doesn’t match the drapes, she has brown hair naturally

  32. PunkA

    This the best you can do “Fish”?? Pretty sad, indeed. Yhis chick is about as now and happening as the Bubonic Plague and syphillus. Which I think she might have just overcome. The Plague, I mean.

  33. Umm. Paging Mr. Fish. I can sit here and shield my eyes from the sun reflecting off her whiteness,or you can post again, or I can do some work! Which is it?

  34. PunkA

    I think her chest was about to cave in and implode on itself.

  35. Frick!

    Good God, if I owned a store and she was carrying a bag with my store’s name on it…I’d have her mugged before anyone could see her carrying it (not violently mugged, mind you!)
    “Stanley!” (maybe she’s trying to do a Mrs Roper impersonation)…”Yeh,yeh,yeh Helen”…

  36. Eric

    I think she lost a bet

  37. El-Coyote

    She must a scrapper… I never figured a 80 pound woman would have the moxy to mug and strip a Hari Krishna….. Go Debra!!

  38. PunkA

    Wow. The circus called and the clown needs its costume back. Bitch even stole the wig and nose and make up (see bag in hand). Celebrities think they are so entitled.

  39. o

    NO way man, what is she thinking?!

  40. Mokey

    this is the best picture i’ve ever seen

  41. Anonymouse

    All that money and she still picks the ugliest mumu off the rack?

  42. Sheva

    No way do I want anything to do with pasty faced tent woman.
    Under that tent it’s no carnival either.

  43. I didn’t know drapes could be such a fashion statement.

  44. Captain Sloppy

    That outfit takes me back to 1963 when my grandma used to wear these things called “Hostess Gowns.” She’d invite the girls over for bridge and they’d chow down on Rice Crispie Treats and whip up some grasshoppers in the blender. I don’t mean frothy alcoholi-laden grasshoppers, I mean real grasshoppers.

  45. nagger please

    She’s practicing for the Macy’s Day Parade..

  46. nina

    what a mess !!!

  47. This has to be one of the funniest pictures on this website in a long time.

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