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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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Credit: BM; Photos: BauerGriffinOnline
Posted to: Jessica Simpson

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  • sol


  • Kally

    No need to wonder Jessica is pregnant!!

  • abby

    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

  • anonymous

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

  • sasha

    she’s too darn cute, even in casuals

  • s

    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.

  • Kaylin

    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.

  • julien

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

  • jim

    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…

  • brie2009

    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!

  • Mojo

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

  • Blind Item

    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.

  • Mojo

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

  • Amy


  • * VICTORIA *

    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 !!!!!

  • Tina

    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.

  • Kate

    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.

  • Torri

    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.

  • Benne

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

  • Soap is good

    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

  • alicia

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

  • ericka

    hahaha i agree alicia
    she is beyond stupid

  • James

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


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

  • Beatrice

    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 bitches 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 @$$.

  • Kay

    ^^ You’re right, he’ll never win the Superbowl as long as he’s with Jessica.

  • lakers fan in boston

    she looks especially stupid with tony romo’s hat

  • Love her

    I love Jessica!!! She’s so cute!!!

  • sAM

    Stop with all the pregnancy rumours!! People said the same thing LAST YEAR and she proved y’all wrong….All who women who gain weight would have bigger stomach…geez!!

  • sandy

    She is a beautiful girl. She may not be as talented as Beyonce but she has a pretty voice and has more talent in her finger nail than Paris Hilton has in her whole body.

  • Cassie

    Poor Daisy….Jessica is carrying her just like Palin carries her baby.

  • Texasstarfan

    Does Jessica Simpson own a brush?

  • Massie

    What laptop is that?
    I think it’s a macbook pro that she got done from colorware

  • Jaye

    There are some stupid post in here as usual. This woman doesn’t appear to crave attention like some celebrities, nor is she always in trouble. She seems decent enough, but people have nothing better to do than to diss her. I’m sure she wants want any human being wants, marriage and kids. Tony is a big guy I’m sure he can look after himself and if he didn’t want to be with her he wouldn’t be. None of you are privy to any special information about their relationship.

  • http://!E Shhhh!

    Tony better mary her by Feb. or end of May. Engaged by Feb, Valentine’s Day. If not,if he does not, then Jessica WILL get pregnant. There is not way this relationship can end. She and her dad, family, and her camp have invested too much time and her name in this relationship.

  • Karen

    That blind is about Mariah Carey and Nick Cannon. Mariah was rumored to be a call girl b4 making it big.

  • Seraphina

    I watched a bio of Jessica way back and on it she was a straight A studen and in the tops of her class. The dumb girl was an act with the Reality show with Nick.

    As far as talent I mean she is better than some and not as good as others. She is a better actress than Beyonce – but not a better singer, she is a better singer than Paris and a better actress, She is a better singer than Lindsay Lohan but not a better actress and the list goes on and on…

  • [☆I n F a m o u s☆]

    d-list loser.

  • Mark

    I don’t believe she was a straight student because she is dumb as hell. Why do she think she has to get knocked up to secure a man. A smart person would count on her relationship to mature with her boyfriend instead of trapping him.

  • Mark

    Does Jessica know how to brush that rat’s nest on her head?

  • Jughed

    She looks great, and the best part is we all know she has a freakishly hot body underneath all those loose clothes that I hope she’ll let us see sometime soon! :)

  • itstruagain

    Comfy casual = slob?
    I’ve never thought she had a good voice, she always looks like she’s having a seizure when she sings. Never understood that.

  • Jenna

    Wasn’t she photographed wasted a week or so ago? Had people helping her walk, I believe. I don’t believe she is pregnant.

  • Miley Cyrus

    What a cute little dog.

    And good on her for not worrying about walking out of her front door dressed casual. I hate these ‘celebrities’ that cant or wont leave their house looking absolutely perfect.

    They are human too, and sometimes dont feel like looking perfect, and they shouldnt worry about it. It really does my head in when the tabloids take a pic of a celeb which looks like….shit, then put it as a page 2 story in big headlines saying as much.

    Go Jess – you rock! Love the house you just bought too. Tis stunning

  • Josh

    She is so ugly. I agree she is a loser.
    Tony should know when you lay down with dogs you get flees.

  • Tina

    She looks terrible, no ass, stumpy legs, a butt face and oversized honker, all capped off with a disgusting rats nest. Even all her surgery can’t make her look decent.

    And she’s been fat for more than a year, if she managed to squeeze anything out of her fake, gay boyfriend she’d have had it by now.

  • Dyna

    How in the world did Jennifer Aniston and John Mayer get dragged into this thread? LOL. I just hope Jessica’s dog doesn’t mind being dragged all over the place when she travels. Poor thing always looks so scared. (Her dog, not Jessica.)

  • fan

    Jess ROCKS!!!!!

  • notafan

    She is so ugly…that nose and those fake lips. Her hat makes her nose look even bigger and bumpier because it draws the eye right to it, forcing you to focus on its bumpy largeness.

    She’s fat. She’s not pregnant. There were pictures of her last week leaving a club drunk and pregnant women are not supposed to get lip injections which she is obviously doing.

    I guess if anyone would be stupid enough to drink while pregnant, she would be. She would also be vain enough to risk harming a baby, so she could get fish lips.

  • crystal

    To all the five Jessica Simpson fans in the world, please get a clue. All this girl does is crave attention. Everyone knows it is a common practice for the Simpson crew to call the paps themselves. Since she can’t sing or act, she has to get publicity from somewhere, and the tabloids is where she makes it big, no where else. As far as her relationship goes, we are not privy to it, however, she is the one who puts it out there herself. No other celebrity puts her relationship out there like Jessica. Once again, her relationships are the only publicity she can get. So if you want to spend your hard earned money on this c-list celebrity, go ahead and buy her ugly purses and shoes. The least you can do is credit the rest of us with having taste for disliking her.