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Jessica Simpson Is Pretty In Plaid

Jessica Simpson Is Pretty In Plaid

Jessica Simpson spends some time with her mother Tina Simpson in New York City on Wednesday (December 23).

The 29-year-old singer was also spotted making her way out of her sister Ashlee Simpson-Wentz‘s home as she headed to a midtown office building. After her business meeting she went over to Ashlee’s Broadway show Chicago.

Jess did a little Christmas shopping at Barneys and FAO Schwartz the day before.

15+ pictures inside of Jessica Simpson being pretty in plaid…

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52 Responses to “Jessica Simpson Is Pretty In Plaid”

  1. 1
    lexy Says:

    I don’t know how pretty she looks without her make-up.

  2. 2
    Jappel Says:

    So beautiful without makeup! Keep this look, Jess!

  3. 3
    maxx Says:

    Without makeup and with her hair down she reminds me of vintage Jessica from early in her career. Prettyyyyy

  4. 4
    vbn Says:

    Ugly. She looks like clone of her father. Totally tranny.

  5. 5
    pocketrocket Says:

    without makeup she looks like a white trailer trash from Dallas working at Wendy’s

  6. 6
    Dieter Says:

    Beautiful withou make-up !!!!!!!!!!!!!!!

  7. 7
    meme Says:

    she dresses like a little girl in mini skirts….dress your age jess…..
    and stop wearing all the fake hair…..u r fake…fake…fake…..

  8. 8
    nativenyker Says:

    She looks way chubby-poo! Girl… Have a salad!

    Rants, Thougths & Merde

  9. 9
    Lara Says:

    WTF is she wearing??? But she looks pretty without make-up.

  10. 10
    annab Says:

    I agree….she does look good without makeup. Wow…it’s a gift when you can do that.

  11. 11
    Isaiah Says:

    She’s so f*cking gorgeous.

  12. 12
    Adri Says:

    She looks very pretty without makeup. She looks thinner too. Really like her boots.

  13. 13
    Adri Says:

    She looks very pretty without makeup. She looks thinner too. Really like her boots.

  14. 14
    JAKE Says:

    I wish my girlfriend looked as beautiful as Jessica without makeup.

    She looks breathtaking here.

  15. 15
    Nic Says:

    she looks huge

  16. 16
    Marta Says:

    this is really bad outfit.
    she doesn’t look beautiful , she doesn’t look bad without makeup, she looks just normal.

  17. 17
    lexy Says:

    LOL! She’s breath-taking all right – it’s amazing how much make-up she wears. At least do what the other celebs do and get some big sun glasses!!

  18. 18


  19. 19



  20. 20

    WE CAN HAVE A BALL OF OUR OWN!!!!!!!!!!!!!!!!!! HAHAHAHA


  21. 21

    LET’S GET TOGETHER???????????????????????? HAHAHAHA


  22. 22
    ladym Says:

    She looks prettier and younger! I hope she sticks to the minimal makeup.

  23. 23
    Josh Says:


    I love her

  24. 24
    Steve Says:

    She’s very pretty, and for all the haters, she’s not fat, she’s healthy, a rareity in Holl;yywood!!!

  25. 25
    infamous Says:

    total fashion nightmare. where to begin. how about just a moving violation for getting it all wrong.

  26. 26
    Britney Says:

    You can tell Jessica read that she look good without makeup she hasn’t wore any since that day.

  27. 27
    Sarah Says:

    Where has this Jessica Simpson been?, she looks WAAAAY much prettier w/o make up. Life w/o Tony is looking good so far.

  28. 28
    lexy Says:

    She’s been wearing make-up…it’s obvious from this pic that she has been wearing make-up while shopping and hanging out with her family in NY.

  29. 29
    I n F a m o u s l y C o o l Says:

    this girl has failed in damn near every aspect of her life yet she still remains in the public eye. why hasn’t she gone broke yet? where’s the money coming in coming from.. she needs to go broke, get fat, and disappear.

  30. 30
    Tim Says:

    Jessica hasn’t failed at everything she can sell shoes..Britney and Christina don’t have a shoe line.

  31. 31
    Ronda Says:

    I’ve always really liked Jess. She’s beautiful but most important she seems to be a strong Woman. I admire her.

  32. 32
    Lori Says:

    Jessica looks so happy and beautiful. Her relationship with Billy Corgan seems to be going well.

  33. 33
    I n F a m o u s l y C o o l Says:

    marriage – fail / done
    pop career – fail / done
    country music career – FAILED. finished before it started.
    idk where you’re from but here in NYC bishes don’t rock jessica simpson anything. you and your friends might, wherever yall from that trash might be cool. ahahahahahahahaha

  34. 34
    Lulu Says:

    she looks great without makeup
    and she’s naturally beautiful, much prettier than her younger sister

  35. 35
    jessie Says:

    she’s not ugly but shes not pretty without her glam. if you think shes pretty its like thinking joe simpson is pretty…no make-up is not working for her, she looks exactly like her father…yuck. she isnt fat but she isnt thin, shes like what 135 at 5’3…she should be 120..i dont think jessica is that pretty anymore she lost her beauty…along time ago.

  36. 36
    lakers fan in boston Says:

    u can kinda notice she’s gaining weight
    her face is starting 2 get fuller
    horrible outfit, just looks tacky
    i will say she doesnt look that bad without makeup
    i imagined much worse

  37. 37
    Jen Analstan Says:

    She should get married soon!

  38. 38
    b Says:

    She is chubby. She looks like a man.

  39. 39
    Hi Says:

    She looks fabulous without her make up. Natural power is the way to go. She looks happy, pretty and on top of her game. Love Jess!

  40. 40
    Lou Says:

    Jessica Simpson Is Pudgy In Plaid!

  41. 41
    =Logan= Says:

    She looks beautiful, especially without make up. It reminds me of her look back in the day when she was on Newly Weds. She was so gorgeous and natural.

  42. 42
    Mrs. Claus Says:


  43. 43
    Mrs. Claus Says:

    @I n F a m o u s l y C o o l:

    Pop=did so – so there but left it for CM

    Money,she is worth around 75 million from her shoes,handbag,line found at aqverage. dept stores-Dillard’s,Macys.
    Dessert perfume/lotions/lip gloss was a money maker and based on marriage with Nick.
    Her JSCollection is expanding and has expanded to kids collection,dresses, the works!!!
    Google JS Collection.

  44. 44
    meme Says:

    most overrate person ever…nd whats wrong with the nose??

  45. 45
    Ivana Serbia Says:


  46. 46
    Kelly Kleavage Says:

    She always looks good, she’s not a dumpster

  47. 47
    ally Says:

    Awww, she looks so cute! And she looks so young without makeup! Lucky girl! :)

  48. 48
    clyde Says:

    She’s so stout and sturdy–like a miniature work horse.

  49. 49
    Stone Says:

    What happened to her???

  50. 50
    Chef Jacke Says:

    Whoever dressed her needs to retire.

  51. 51
    MMA Says:

    Maybe at Green Acres.

  52. 52
    SpacyTracy Says:

    I’m no Jessica fan, but she is not fat at all. She still has a defined waistline, and she looks healthy. To those who say she’s fat and should eat salad, I suppose you must all be perfect, thin supermodels, right? If you’re not, you certainly have no right to criticize someone else for her weight.

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