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Jessica Simpson: Dressed Up or Dressed Down?

Jessica Simpson: Dressed Up or Dressed Down?

Jessica Simpson dresses conservatively while dining out at Country Restaurant at Carlton Hotel on Madison Avenue on Thursday afternoon in NYC.

The Blonde Ambition actress then dropped a few thousand bucks at the Roberto Cavalli store.

To the left, Jessica at the Costume Institute Gala on Monday in NYC.

Which do you prefer? Jessica Simpson — DRESSED UP or DRESSED DOWN?

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Photos:, Evan Agostini/Getty
Posted to: Jessica Simpson

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34 Responses to “Jessica Simpson: Dressed Up or Dressed Down?”

Pages: [1] 2 » Show All

  1. 1
    Anthony Says:

    She looks great no matter what, but there’s something so sexy about her when she’s dressed down and natural

  2. 2
    Ava Says:

    does she have something done to her lips???? they look bad

  3. 3
    Shoes4life Says:


  4. 4
    bowow Says:

    Dressed down is better. It’s like she tries too hard to be sexyssss dressed up.
    She’s such a natural beauty!

  5. 5
    Jess's face looks wierd Says:

    This outfit is nice, but the lip injections are making her face look wierd, her smile,nose ect..looks wierd what has she done to her face?

  6. 6
    Hey Now! Says:

    Dressed down I can not stand to look at her anyways lol. She has looked so “off” lately. She really has lost her appeal.

  7. 7
    Katerina Says:

    I also like the dressed down version better. She looks like a transvestite in that gown and it is definitely not a classy look with only her nipples covered up and the rest of her boobs on display…

  8. 8
    sharlene Says:

    neither, shes getting to old now. she use to be bautiful back in the first season of newlyweds. to much plastic surgery and shes just loosing her looks dramatically. NEITHER!!!

  9. 9
    Snarky Sharky Says:

    Dressed down, she looks almost normal there and even cute

  10. 10
    ammy Says:

    Neither, she look like a man. She’s pretty before, now she look unnatural.
    I don’t like her anymore……

  11. 11
    [Fug Face [You]] Says:

    ugly hair color, ugly lips, ugly nose, mannish face, horrible dresser, hideous orange tan [the Oompa special].

    she looks bad dressed up and down, to think at one point earlier in her career she was actually ‘cute’. oh well she better stick to media who-ring cause her music career is Finished

  12. 12
    Linda Tow Says:

    She looks better dressed down, but ultimately she tries too hard and doesn’t have the astute dress sense to be able to carry off versatile designer looks…she’s just a Southern girl who got lucky.

  13. 13
    Shmoo Says:

    Neither. She’s always dressed wrong and looks overdone.

  14. 14
    Tallchic Says:

    Down definately! She needs to stay away from the red lipstick. Something is VERY wrong with her face!

  15. 15
    creativegirl Says:

    Yeah, I hate to say it but she doesn’t look good. Does anyone even remember the fresh faced girl in the With You video? It wasn’t that long ago, but gosh she just has gone downhilll terribly. Her boobs really look 10 times larger than they ever were and they look fake now in most pictures when you see them, I wonder if she had them done? They were so nice and natural looking before, now they look like globes up under her chin. I don’t know Jess, you really screwed up letting Nick get away.

  16. 16
    ('@') Says:

    Neither way

  17. 17
    Sara Lee Says:

    Neither! She’s not natural looking anymore, and even without makeup she has this conceited look about her. Go away

  18. 18
    ilovehugh Says:

    so sad for her. She used to actually be quite pretty. Why do these girls in Hollywood always think that more is better. More boobs! More lips! Leave good enough alone. I have always thought that natural beauty is always better. But that is just my opinion.

  19. 19
    Mmmmm Says:

    It is her lips, she got some injection before but said she would never do it again but looks like she did.

  20. 20
    irene Says:

    its her lipstick not injections they put it over her lip outline and the red color doesnt do her justice she looks beautiful in natural colors and her chest is all natural!

  21. 21
    Laura Says:

    She was always so beautiful when she was just lounging around her house, on Newlyweds…

  22. 22
    Mary Says:

    Is that dressing down??? I thought dressing down was wearing jeans and flip flops and a cute shirt. I guess I was wrong

  23. 23
    Mary Says:

    OH yea, I think the fame got to her. She’s not down to earth anymore

  24. 24
    zack Says:


  25. 25
    nick Says:

    excuse me MARY but how the hell do you know if she’s down to earth or not
    are you judging her from a picture :S
    you don’t even know her or talked to her lately
    if you don’t like her, that doesn’t give you the right to say fake and stupid stuff

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