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Jessica Simpson is Comfy Casual

Jessica Simpson is Comfy Casual

Pop-turned-country songstress Jessica Simpson goes for a super casual look as she and her dog get ready to fly out of the airport in Burbank, Calif. on Friday (January 16).

Jessica kept it comfy in a houndstooth newsboy cap, wide-legged jeans, an oversized grey sweatshirt and cute red-toed socks. Like many of us, seems like Jessica just can’t leave the laptop at home.

5+ photos of comfy-casual Jessica Simpson inside…

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51 Responses to “Jessica Simpson is Comfy Casual”

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  1. 1
    sol Says:


  2. 2
    Kally Says:

    No need to wonder Jessica is pregnant!!

  3. 3
    abby Says:

    I like Jessica stlye of clothes she wears and then there’s Jessica Biel no style at all
    even though Jessica Biel supposedly has a big butt depending who you ask

    Jessica Simpson wears William Rast jeans much better

  4. 4
    anonymous Says:

    Tony doesn’t look to be very supportive of her career. He should be at her first concert.

  5. 5
    sasha Says:

    she’s too darn cute, even in casuals

  6. 6
    s Says:

    I was wondering if she was pregnant, she certainly looks pregnant. I know that she has looked like she’s gained weight recently, but in these pictures she looks preggers to me. It might just be the oversized sweater though.

  7. 7
    Kaylin Says:

    Try putting a huge sweater on, you all would look pregnant too.
    Tony has been with her in LA this whole week, now he needs to take care of his business in Dallas. Who cares if he misses the first one, he cant make them all.

  8. 8
    julien Says:

    Wowow…not a lot of effort this morning getting out of bed!!!!

  9. 9
    jim Says:

    I still liked her better with Nick…She and Tony won’t last long at all if her dad has anything to do with it…

  10. 10
    brie2009 Says:

    I love her handbag collection. I almost got one from ebay but I needed to know how big the bag will look on me and I haven’t seen it in person.

    But anyways isn’t that the dog that Nick gave to her when they were together? It’s cute!

  11. 11
    Mojo Says:

    She look like sh!t
    All of these Hollywood ho are so fake.
    She and Jennifer are just a like.

  12. 12
    Blind Item Says:

    Blind Item

    BlindGossip – Yes, she is definitely pregnant. So why isn’t she announcing? Because there are two more pressing issues with which she is dealing. The first is that her relationship with the baby’s father is rather tenuous right now. Friendly in public, but lots of stress and squabbling in private. The second reason is that her very aggressive attorney is trying to wrangle down the source of some hurtful information about her that would certainly tarnish her image. So the pregnancy isn’t exactly at the top of the list in this trio of life issues.

  13. 13
    Mojo Says:

    I hate that cheap hair weave. The dog hair looks better and all of her cr@p look cheap

  14. 14
    Amy Says:


  15. 15
    * VICTORIA * Says:

    Whether she is pregnant or not, I don’t care one way or another……
    That silly hat she has on, needs to be placed back on her shelf……..They only look good on SOME MEN, ONLY…….On a woman, it looks like their playing ” house “………Silly looking !!!!!

  16. 16
    Tina Says:

    Yeah….She and Jennifer Aniston want all of the media controversy they can get to keep attention on themself. If she is pregnant then I believe she got knocked up on purpose to trap Tony like her sister did Pete. Who would think that cheap pathetic trick would still work here in the 2008-2009.
    These are very stupid men that are dumb enough to let a cheap women trap them.

  17. 17
    Kate Says:

    That stupid hat is trying to cover that hideous weave.
    Jessica saw the knocked up trick worked with douche bag Pete guess papa told her to try it for Tony. Oh well poor stupid Tony he should have saw it coming. Imagine Jessica and her stupid crew being smarter than Tony lol.

  18. 18
    Torri Says:

    Keeps that lap top so she can go on line and read comments, then post good comments about herself. She ain’t’ nothing but a desperate hound dog.

  19. 19
    Benne Says:

    Pregnant…..that’s why John Mayer wants to stay wayyyy clear of her. Like she is the plague.

  20. 20
    Soap is good Says:

    jessica should have stayed with nick. oh well now she’s knocked up with some random athlete to get publicity. nice christian values. i wonder does she regret saving herself for nick? it didn’t seem to matter. lol

  21. 21
    alicia Says:

    this girl i soooooooo dumb, she really makes american girls look bad

  22. 22
    ericka Says:

    hahaha i agree alicia
    she is beyond stupid

  23. 23
    James Says:

    I don’t think Romo will ever win the SB dating her

  24. 24
    DAVID COOK Says:

    she’s playing a bad role model and she likes it :)

  25. 25
    Beatrice Says:

    If she was actually talented at something, I would not hate her as much. But she gets all this attention not because she is good at her music, or acting or whatever else she has tried etc. country. She is only relevant because of who she dates. If she had no boyfriend, nobody would even care what she is doing. Her album tanked, her movies go straight to DVD, so what would there be to right about?

    Jessica is equivalent to Paris, lindsay, Heidi and all those ******* who are only famous for their personal life and not professional.

    So for all you wondering why Jessica gets hated even though she has no sex tape out or has never gone to jail or rehab, it is because she does not deserve the attention she gets. She is good for nothing. She is lucky Tony is giving her the time of day, but its not because he loves her, its because nobody else wants him now that his d*ck has been up her @$$.

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