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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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Photos: Bauergriffinonline, Famepictures
Posted to: Jessica Simpson

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  • lexy

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

  • Jappel

    So beautiful without makeup! Keep this look, Jess!

  • maxx

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

  • vbn

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

  • pocketrocket

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

  • Dieter

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

  • meme

    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…..

  • nativenyker

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

    Rants, Thougths & Merde

  • Lara

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

  • annab

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

  • Isaiah

    She’s so f*cking gorgeous.

  • Adri

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

  • Adri

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

  • JAKE

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

    She looks breathtaking here.

  • Nic

    she looks huge

  • Marta

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

  • lexy

    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!!







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



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


  • ladym

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

  • Josh


    I love her

  • Steve

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

  • infamous

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

  • Britney

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

  • Sarah

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

  • lexy

    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.

  • I n F a m o u s l y C o o l

    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.

  • Tim

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

  • Ronda

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

  • Lori

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

  • I n F a m o u s l y C o o l

    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

  • Lulu

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

  • jessie

    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.

  • lakers fan in boston

    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

  • Jen Analstan

    She should get married soon!

  • b

    She is chubby. She looks like a man.

  • Hi

    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!

  • Lou

    Jessica Simpson Is Pudgy In Plaid!

  • =Logan=

    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.

  • Mrs. Claus


  • Mrs. Claus

    @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.

  • meme

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

  • Ivana Serbia


  • Kelly Kleavage

    She always looks good, she’s not a dumpster

  • ally

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

  • clyde

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

  • Stone

    What happened to her???

  • Chef Jacke

    Whoever dressed her needs to retire.

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