Jessica Simpson wears unfortunate leggings in Aspen, didn’t get married


Here is the fashion industry’s billion-dollar baby, Jessica Simpson, and her paid escort Eric Johnson in Aspen on New Year’s Eve. Don’t ask me what Jessica is wearing. I mean, I get that it’s really cold in Aspen and that Jessica’s center of gravity is off because of some weight gain (thus, the boots), but there is absolutely no excuse for those leggings. There’s no excuse for the entire outfit combination, but the leggings in and of themselves make me wonder if Jessica should perhaps be institutionalized. Surely, she’s trying to look bad, right?

Anyway, it looks like I was wrong. It looks like Nick Lachey’s Jedi mind trick didn’t work. Jessica Simpson did not get married on 1/1/11. Instead of getting hitched, they spent New Year’s Eve at some kind of dinner, which probably involved the consumption of a whole lobster, a ham, and an entire bottle of Jack Daniels.





Photos courtesy of Fame.

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91 Responses to “Jessica Simpson wears unfortunate leggings in Aspen, didn’t get married”

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  1. dragonfly says:

    What, no 5-inch platform eskimo boots?

  2. guesty says:

    ham as in hocks!! ha. jess please hire a trainer & stop drinking so damn much! & those leggings are a no even if they are christmas pajama bottoms.

  3. Po says:

    I’m just so confused by the legging boot combination. It’s like a few years ago when she wasn’t obese by any means but chose to wear those horrible mom jeans. Then she got mad when people talked about her weight but she is the one who accentuated it. I think her problem is a lack of style, which a lot of us are cursed with, but the difference is that the rest of us can’t afford a stylist and didn’t put out a fashion line.

  4. brin says:

    I love that she has her pocketbook with her because she’s the one who is paying for everything.

  5. CooCooCatchoo says:

    Its official: she’s our blond Snooki. .

    What’s up with her man-chin? She could hold a quarter in that cleft!

  6. LunaT says:

    Dude, I don’t have a stylist and I could do waaaaay better than that w/clothes from Target. Not to be mean, but it seems like the Britney Spears and Jessica Simpsons will always have a little bit of tacky. Seem to be sweet girls that sincerely keep trying, but it’s not working.

  7. Kevin says:

    Is she telling someone to pull her finger in the second photo?

  8. mojoman says:

    where is her neck? every time I see her pic, she looks stockier and rounder. Bless her for being happy but man, take it easy on the alcohol..

  9. womanfromthenorth says:

    No Horizontal stripes on heavy people!

  10. emo21 says:

    paid escort? unfortunate leggings? i can’t imagine anything more unfortunate than a blogger hammering misgivings on new year’s day.

  11. malachais says:

    She looks like some kind of burnt snow smurf. Good grief.

  12. whateva says:

    all you white women ever talk about is weight this weight that wtf… if she is happy how she looks why do you care, damm go eat a burger or something

  13. bubbles says:

    God, you people are evil. whilst her outfit truly is unfortunate, she looks happy. let the girl be happy and fat and unfortunately dressed if she so choses to.

  14. albeli says:

    The leggings are god-awful, and while her “style” sense is pretty bad, she doesn’t quite sink to the level of Britney. I do wonder how Jess and Brit can have all that money and not be able to hire decent stylists.

  15. Kitchendancer says:

    I like the leggings!

    I’d like them better with a longer shirt/dress or skirt – something that goes to upper mid-thigh level would be best. Still… I like them. Leaping reindeer!

  16. motheroftheyear says:

    I am convinced she is letting herself go only to start working out/losing weight in a few months so she can nab a People or UsWeekly “look how much weight I lost” cover. Either that or some flab-to-fit type reality show.Anything to attempt to stay relevant.

    No way in hell she’s getting married as a fatty.

  17. Liana says:

    i can’t imagine anything more unfortunate than a blogger hammering misgivings on new year’s day.

    It’s not New Year’s Day anymore.

    I think she looks cute in that last picture, but the leggings… no.

  18. serena says:

    Call me crazy but I find those leggins cute..

  19. Kazoo81 says:

    i like her bag. ignoring the rest of the outfit.

  20. Trillion says:

    #10, note the name of this website. Maybe you should be perusing instead.

  21. Faye says:

    I’d definitely wear those leggings. Not with that outfit, but I’d make them work.

  22. Weeble says:

    It’s not even that serious…I mean really you would think this girl weighed 700 pounds or something. Cut her a break! And anyway it’s not the leggings that throw off the outfit. It is the boots. Keep calm and carry on…

  23. maria says:

    I love the leggings, but the boot are killing me. And she should try a cute hat or ear muffs. She is pretty on the outside, but I am not sure what is inside of her. I wish I could buy a new guy toy. Good luck to her – stay ignorant and blissful, Jessica.

  24. malachais says:

    The outfit sucks but she is not fat in my opinion. I don’t get the “double-chin” references, quite frankly I don’t see one. Maybe a bit thick but she is not “fat” by any means.

  25. Rio says:

    She looks so short! It’s weird- maybe it’s because I’m not used to seeing her in flats? She looks so tiny, especially in the first picture.
    As for the leggings, meh. They aren’t horrible, but I’d have worn them with a mid-thigh skirt.

  26. junipergreen says:

    The outfit is atrocious (of course), but I have to say…she looks absolutely beautiful, in my opinion. Without the makeup on and smiling she looks great. People need to lay off her weight. If she was thin people would say she was too thin. Now she looks perfectly average and she gets called fat. No wonder women have body issues. No one is good enough no matter what–only (completely subjective) perfection will do!!

  27. Tifygodess24 says:

    I highly doubt she has anything to do with designing her clothes etc. , because she wears the most horrible outfits. She seems to have no sense of style or pride in what she wears. She’s just the name who gets to collect the money for other peoples hard work. Too bad there are actual talented designers ( not to mention singers ) out there who deserve to be where she is and in the spot light. But Money builds money , those without it are out of luck. Talent or not.

  28. SRM says:

    She looks happy.

    However, I think her coat is trying to eat her.

  29. lucy2 says:

    She rarely dresses in a flattering way, but this outfit is exceptionally bad for her. She’s not fat, but she’s not stick skinny either, and she’s fairly short – a decent stylist would have her looking great.

    #16 I think you might be on to something with your weight loss publicity theory.

  30. Marjalane says:

    Yeah, you could institutionalize her, but she’d just chrew through her straps.

    And for all of you who want us to say nice things about Jessica: “I think she and her ladysitter look better than most of the married couples I saw at the last PTA meeting I attended.”

  31. Ron says:

    Next Christmas instead of an ugly sweater contest, let’s have an ugly leggings contest! Jess, can I borrow you cute deer leggings?

  32. anti says:

    those tights are basically the horizontal pattern she does NOT need around her thighs.

  33. JenJen says:

    Shocked they didn’t get hitched on New Year’s. He must be holding out for more $$$ in the pre-nup. She looks like a idiot,just trying to fit in with the locals (LOL).

  34. JenJen says:

    To be fair,he has no fashion sense either,
    his outfit is so mis-matched it horrible. Too bad this fashion mogul is clueless how to help him.

  35. Alarmjaguar says:

    I think that her face looks beautiful framed by the coat…I wouldn’t have worn the leggings myself, but I applaud that she is having fun with the season.

  36. Rosanna says:

    I like this woman, even when she wears awful leggings 🙂

  37. t says:

    She looks gross in the leggings. Here is some more Jessica grossness. Gawker has reported that Jones of New York (the company that designs jeans that later get labelled “Jessica Simpson”) has launched an investigation into who is flinging used tampons all over their headquarters.

    These Jones Of New York executives really have no idea who in their association could be capable of such disgusting unhygienic behavior? If I were them, I’d look no further than the Jones Of New York meeting room. And follow my nose to the chair occupied by the woman with the unwashed hair( ),
    loudly passing gas( )
    while trying to rub three days worth of plaque build-up off her teeth with the sleeve of her sweater.

    I wonder if this Jones of New York grossness has mysteriously stopped since Jessica has been in Aspen being gross in her leggings.

  38. Lori says:

    I think she looks fine except for the leggings. She looks happy!

  39. Jayna says:

    OMG. Jessica, Jessica, Jessica. She’s not getting any thinner, either. She was such a stunning bride when she was younger.

    Her boyfriend has the dweeby-ish face.

  40. gg says:

    What does she do again besides design unhealthy marked-up shoes?

  41. xxodettexx says:

    hah, thanks for the great comments [even some i didnt quite agree with brought a smile to my face]

    i am with the very small chorus that are loving these leggings, but then again, ive been accused of having eclectic tastes

    hope this rushed relationship brings jess some happiness [though my cynical nature doubts it]

  42. mamasnail says:

    @whateva…going to get that burger. I agree with you, I don’t think she’s that fat and whose business is it if she is?

  43. DrM says:

    Oh for the love of GOD! Girlfriend is NOT obese or hideously overweight. She’s fine! The outfit however is not. The leggings would look odd on a stick insect! I’d wear them around my house in winter with a thick sweatshirt…not out and about. The jacket is fab and so are the boots just not put together as an outfit.

  44. wunderkindt says:

    A deliciously fug outfit.

    The leggings are so bad that they’re good!

  45. TeeTee says:

    I like her bag and make-up…

    the rest-NO!! SHE REMINDS ME OF A CHUBBY DOLLY PARTON-BEFORE SHE HAD SURGERY OR WHATEVER YEARS AGO..her coat is too damn tight, especially around the mid section. she would have been fine in black leggings w/a colorful top maybe..

    just no further comment! smdh! she does it to herself! her petite frame will start to suffer if she does not watch all of the gluttony.

  46. Mizz Tickles says:

    I’d wear the leggings 🙂

  47. Someone Else says:

    @motheroftheyear —

    That would not surprise me in the least. I think you’re onto something…

  48. HEB says:

    Say what you want…she’s got everything she wants now…a bunch of money and her very own Nick Cannon! Who cares what his motives are as long as he stays in line!

  49. Leek says:

    Even the deer have camel toe.

  50. Shannon says:

    Aww I think the leggings are cute. They’d be too much if she was wearing anything else with a pattern, but she’s in all black so I don’t think it’s too busy. Plus, Aspen is.. Aspen. Ski chic merges comfort with cute wintry fashion and furry stuff (real or fake, depending on your preference).

  51. Megs says:

    She may look ridiculous, but she actually looks really happy compared to how she used to look.

  52. bagladey says:

    I like those leggings.

  53. birdgherl says:

    Those leggings would be adorable on someone who was 6 feet tall and rail thin. And she is not going to walk down the aisle fat. My prediction is a massive detox/diet and a Spring/Summer wedding.

  54. mystified says:

    I love your use of the term “unfortunate”; has that become the new “bless her heart”?

  55. Sumodo1 says:

    Bless her heart, she’s pregnant.

  56. chasingadalia says:

    Maybe she’s waiting for 11:11:11 on 11/11/11.

  57. kelly says:

    Listen to you people! Hate her because she’s dumb and obnoxious, not because she’s actually eaten something over christmas. She’s not even really overweight! Get off your haterhorses. Big tits are often granted at the expense of a neck.

    Those tights are stupid but I would totally wear them just to piss people off.

  58. Bubbling says:

    I don’t think weight is ever coming off. I think this is her natural and what we have witnessed in Daisy Duke was just starving and crazy/obsessed/Biggest looser workouts. And she didn’t have style to save her life even back then, but we were looking at her, not what she wears, so that just went by us like it’s okay

  59. Liana says:

    Get off your haterhorses.


    OMG, that was so deliciously juvenile that it made my cold and bitter heart melt all over my keyboard.

  60. Belle Epoch says:

    The ginormous designer bag is RIDICULOUS. It’s as empty as her head. How hard is it to carry a credit card to buy your own bling?

  61. DrM says:

    @kelly – I am officially stealing ‘haterhorses’ as my new word…may it catch on here in NZ thank you!

  62. Christine says:

    I don’t think she is fat or overweight. Her breast implants make her look way bigger than she is, as does her low self esteem, and UTTER lack of style.

  63. Ally says:

    Quibble: a billion dollars of plastic rubbish with JSimp’s name on it has been sold. Her cut is just the licensing rights, however, which according to one knowledgeable estimate I’ve read, is closer to $36 million.

    Still not bad for having been a viable starlet some years ago, but not a “billion-dollar baby”.

  64. Johnny Depp's Girl says:

    I still think she’s pregnant.

  65. Crash2GO2 says:

    How cute. She has little reindeer flying over her knees.

  66. MissyA says:

    They totally look like Harry and Lloyd (Dumb and Dumber) trying to fit in with the Aspen trustfunders.

    It’s so damn loud and gaudy – you can see the contempt in the faces of the locals caught in the lens. I love it! Go Jess!

  67. As a stylist, I’m not opposed to leggings with snow boots, but they must be a dark solid color AND worn with a tunic-length top. I agree with someone above, those leggings are sleep pants. I do think she looks happy, and that’s what matters.

  68. Tomas says:

    white trash with money…

  69. munchies says:

    I like her, shes cute. leggings are not bad, just the boots but then its Jessice Simpson, she can wear anything she want, She got Billions anyway!

  70. Luckylilgem says:

    Poor Jess. The media hates her! Called her dumb when she was married. Hated on every relationship she was in post Nick . Finally girlfriend has a chance at a stable relationship, and bloggers are bagging on her man as an escort? Why does the media wan her single and lonely?

  71. Dana M says:

    Maybe she IS Preggers. My waist line was the first thing that was lost both times i was pregnant.

    AND, at the end of the her or hate her…Jessica is the one who is laughing ( or eating) all the way to the bank because she made $750 million dollars last year! Personally, I don’t think she looks fat, she look a little full but that’s okay.

  72. Hakura says:

    Jessica is *not* fat. She’s heavier than she has been for a while, but fat is way out of line. (And she does not have a ‘cleft you could lose a quarter in’. Come on guys.)

    People are being unreasonably mean about her lately. Her clothes are… very unfortunate, yes. The leggings would only work as winter PJ-wear, which wouldn’t be appropriate to go out in. (No, not even to 7-11 or Walmart.) And horizontal patterns are just a horrible idea for *most* people.

    Give her a break. She does look happy (if not.. fashionable.), and not unhealthy. I’m glad to see her out and about.

  73. mimi says:

    She looks so happy!! That being said while the leggings are not working with what she’s wearing I do love the jacket on her. She’s not fat and I don’t understand why people continually bash this girl about her weight. I remember when she was super skinny she did several interviews talking about how she had to workout for hours every day and how she was starving ALL the time-so I think she’s better off now then she was then!

  74. fanny says:

    They both look so content … that’s nice. The leggings are an interesting choice that says she marches to the beat of her own drummer. At least they are black and white instead of in full blown color.

  75. eva says:

    I hope she only wore those leggings because Eric said (and he sincerely believes ) she looks beautiful in them. Maybe love is blind?

    I like that they look happy together. I hope he’s her version of Nick Cannon.

  76. tango says:

    Tacky clothing choices.

    The problem is poor Jessica doesn’t dress for her body type. She tends to wear things that are too tight or styles that accentuate her problem areas like her stomach. Those leggings belong on 6 year olds, not a woman pushing 30 no matter her size.

  77. t says:

    Of course she looks happy. He’s her paid escort and she thinks she can rehab her public image with him (“look, I’m not desperate, I have a man”) . As her employee, he obediently shows up when told to be photographed by Joe (Jessica’s personal pap) and should she decide on a plus-sized Barbie themed sham wedding, he’ll be there dressed as Ken. And for a few extra bucks, he’ll tell her her thighs don’t look big at all in the sparkly, horizontal striped leggings she’s sure to be wearing at the “wedding”.

  78. Manda says:


  79. I Choose Me says:

    Ugh! Not gonna comment on Jessica’s FAILfit except to say I’m so sick of seeing these farking Birken bags being toted everywhere.

    Sidenote: The girl in the turquoise scarf, behind dumb and dumber in the second pic, is cute.

    Edit:@ kelly. Big tits are often granted at the expense of a neck. *Sigh* I hear ya!

    @Missy A. Did not see your comment before I posted re: Dumb & Dumber. Great minds? 😀

  80. crazydaisy says:

    Fat or thin, solids or stripes, the leggings-alone look has always been a major miss, IMO.

    Why would I want to display to every man, woman and child in the street, perverts included, the most private places in my body? My butt and my crotch and my camel toe are my personal business. Hel-lo!

    How degrading, demeaning, objectifying, etc. to stand in line for coffee with my thigh curves and butt crease on stark display to everyone behind me. Like they’re supposed to avert their eyes. What is the point?

    Why don’t we don’t see men walking around in leggings or speedos all the time? Easy answer. Not a good look. So why must women submit to this?

    There’s no honor in being a SLAVE to fashion.

  81. LT says:

    I think the leggings are fun & cute! Boots, not so much.

  82. bluhare says:

    Could his eyes be any closer together?

  83. Hakura says:

    @CrazyDaisy (#80)- The leggings-as-pants look, when not done *properly*… (with a top that’s long enough to come down over the butt/crotch entirely)… Is really tacky.

    I think some of the ‘thicker’ material legging styles (& busier patterns) make some women think it’s not a big deal. But it should be considered the same as wearing ‘tights’ in my opinion, which no one would ever go out in (outside a ballet performance) without proper coverage.

    Not a good look, but I don’t think the idea of ‘leggings’ is necessarily objectifying & demeaning. The basic idea that women’s fashion is always geared toward *showing* the body (where men’s really isn’t)… that’s another story.

    @Bluhare (#82)- No. xD If they were any closer together, he wouldn’t have two of them.

  84. crazydaisy says:

    yes, i agree, hakura. either a long tunic or a mini-skirt over the leggings works for me. maybe even shorts. then it can be v. cute look.

    otherwise, seems like you were in such a rush to get out of the house you forgot to get all the way dressed.

  85. jayem says:

    Wow. Jump on the bandwagon much? She looks just fine, and happy to boot. Don’t be like that, poking fun just because everyone else is…

  86. Erin says:

    Good God, she isn’t that big! I like her, even tho she’s pretty ditzy and I do like her shoes so leave the poor girl in peace! I myself gained 5 lbs over the Christmas/holiday season!

  87. Hakura says:

    @CrazyDaisy – I agree, I really like the way a miniskirt or even the right style of shorts looks over leggings or tights. =) Especially with boots.

  88. Sean says:

    She looks good and the outfit is cute. Are all the writers at this site vision impaired?

  89. Martylea says:

    Like her leggings more than I like his choice in scarves. She looks healthy not hefty so just give her a break. We all have bad photo days.

  90. ashley says:

    OH MY GOD her legs are just fat lol
    Those would look cute on a skinny biitch lol

  91. free says:

    I like her leggings and I like her figure. She is a sweet person, and that is much more important than anything materialistic. Her BF is cute too. Poor celebrities…what do you expect her to do, wear an evening gown in the snow? I live in Canada and you have to bundle up and keep warm, keeping warm is so much more important than impressing anyone.