Jennifer Love Hewitt’s billowy orange dress: tragic or cute?


It’s been a while since we’ve done anything about Jennifer Love Hewitt, so why not? It’s a slow gossip day, and this dress is noteworthy. Honestly, I like the idea of this dress, much more than I like the execution. JLH is (partly) famous for figure, the infamous “Pear Ass” as her ex-boyfriend Jamie Kennedy called it. And pear-shaped ladies should try this general sillhoutte – empire waist, loose skirt masking the pear, showing off your assets (in this case, JLH’s shoulders and bust) and obscuring your faults (JLH’s recent weight gain, I guess, in her mind).

But there’s something that I kind of hate about this look on her. I think it’s a combination of the color – that too-strong orange color-block with the cream fabric on the bottom is not good – and the fact that the skirt is too billowy. All of that extra fabric ADDS weight to your bottom half rather than masking weight on your bottom half.

Two more things: JLH is at an age and a cup size where the girls need to be supported at all times in public. Her bust is simply too big to go braless. I get that she probably thought she couldn’t wear a bra with a dress like this, and she’s right. But the answer is “not wearing the dress”, not “wearing the dress without a bra.” Lastly, hideous bag. Just awful.




Photos courtesy of Fame.

You can follow any responses to this entry through the RSS 2.0 feed.

64 Responses to “Jennifer Love Hewitt’s billowy orange dress: tragic or cute?”

Comments are Closed

We close comments on older posts to fight comment spam.

  1. brin says:

    Were her legs always that stocky or is the dress making her legs look bad, too?

  2. annie says:

    Ugly shoes too. Agree-way too much fabric on the dress skirt

  3. Kaye1 says:

    That handbag is truly terrifying. It looks like it might come to life and eat someone.

  4. mln76 says:

    She actually is doing that breast covering thing you do when you realize you need more support in that area. The dress is decidedly not flattering.

  5. Sue says:

    She needs a bra her boobs look like their down to her stomach if you have big girls you can’t go free boobing it.

  6. Bailey says:

    If I photo-shopped my grammy’s head on Jennifer’s body, it would look like her.
    my grammy is 97 and her body almost looks better than Jennifer’s. No joke

    this dress is for 90 old woman who can make an edible fruit cake.

  7. MikeyAngel says:

    I like JLH but damn, she pretty much did nothing right here. The dress is ridiculous. The color, the cut, the length. Her boobs look bad here. She should not go bra-less whilst trying to look respectible. Her legs look stocky too. This was a fail at all angles.

    Signed Lady of Cheddar

    Oh and thanks to all of the Waity Katy posts, I now refer to my beautiful 6 month old as Alexandria- Our Lady of Crumpets!

  8. Rachael says:

    Did she always have kankles?

  9. Ron says:

    It’s just a little too matchy for me and the cutof the dress does nothing at all for her figure. I was going to say maybe she just needed a “comfy” day, but then she is wearing the not comfort oriented shoes. She truly needs a stylist that can work with her figure. Alot of times girls with curvy figures have a hard time deciphering what works on their body. Hewitt, Hendricks, and Aguliera all come to mind here.

  10. Rita says:

    None of this outfit works for me. As for the bag, recycling Billy Idol’s pants might be good for the environment but it faux fashion.

  11. YAY says:

    we are our own worst enemy. love this site!

  12. melinda says:

    The dress is super unflattering. So many things wrong. The lack of boob support and where it hits on her legs are not flattering, not to mention there is too much fabric in the hip area. Maybe if it were a bit longer and became a maxi-dress? Still wouldn’t solve the boob problem though. That bag, just terrible.

  13. guesty says:

    Jlove that’s a def no.

  14. Siren6 says:

    That bag is truly tragic.

  15. Ruby Red Lips says:

    Dress is blah but the matching bag is hideous! Yuck!

  16. sandy says:

    i guess i am alone when i say i like it, her legs are perfect, not too big or too small, clothes don’t always have to hug to be nice, sometimes we want to just be free and glamorous.

  17. Jane says:

    It looks like she has put on weight, maybe that is why she is wearing a tent, and an orange one at that. So right about the girls needing support. I think I am about her cup size and would never let my girls swing free like that. It is not comfortable and it makes her look matronly, not sexy.

  18. Diane says:

    Thank you, Rita, I knew I’d seen that design before. LMAO Billy Idol.

  19. DogBoy says:

    So what the dress is ugly, the bag is awful, she’s too busty to go braless, she has kankles…
    she’s cute and (now) more like a real person than ever. It’s attractive.
    Sign me up, haters.

  20. Anti-icon says:

    Hate. She has trailer park taste. And execution.

  21. esblondie says:

    I say go on with her bad self with her weight gain; it’s refreshing to see. But yeah, I’m a busty girl and I don’t even hang out around the house without a bra, let alone go out in public. I’ve eliminated a good 50% of clothing as ever being options because I HAVE to wear a bra, and a supportive one, all the goddamned time. On the positive side, It really speeds up the shopping process.

  22. jen says:

    She’d better watch it, she’s starting to Kirstie Alley.

  23. lolas says:

    supremely, supremely tragic.

    Except I like the colour of the straps of her shoes.

  24. Jennifer says:

    And, I’m just going to say it. I hate it when people wear shoes that their toes hang over on the sides. Yuck.

  25. Cirque28 says:

    How to instantly look 20 lbs heavier!

  26. LittleFATMe says:

    I second the TOO much extra fabric is not working to minimize anything, also that the orange on cream isn’t good – maybe broken up with a small strip of the blue in both her bag and shoes and it would be better – but right up against each other it just is not working.
    Also, her feet are falling off the sides of those shoes – is that so that she can claim she wears a size 6 shoe? Doesn’t look cute or comfy!

  27. TQB says:

    The tragedy here is that the dress/no bra/bag combo was so intense you never even addressed the shoes.

    No, she doesn’t have cankles, her legs are just fine, but when you are a shorter lady (and I am), big thick ankle straps do that to your legs. Had she worn this dress with a floppy hat and flip flops I guarantee no one would be talking about it; she’d just look casual.

  28. Maritza says:

    She definitely did not look at herself in the mirror when she decided to go out.

  29. Cheyenne says:

    Fugly from nose to toes.

  30. MSMLNP says:

    I love JLH, don’t really know why.

    I am neutral about the dress, but I passionately hate those shoes with THAT dress and think that is what ruins the look. and the handbag isn’t doing her any favors either.

  31. RHONYC says:

    when good fashion happens to … ‘some’ bodies. 🙁

  32. Venus says:

    I think she is a really pretty, pretty girl but good lawd she doesn’t know how to dress for her body (which, btw, is refreshingly “healthy looking” by LA standards). She could really look great if she would just learn how to compliment it.

  33. moptop says:

    Dreadful. That is all.

  34. Liana says:

    I really really like her. She’s one of the nicest women I’ve ever been set side with, but she never seems to dress well for her body.

  35. Zelda says:

    I like the combination of the shoe colour with the dress colour.

    That’s it. That’s all I got.

  36. curmudgeon says:

    Ah poor Jenny. Leave her be.

  37. junk573r says:

    I guess I didn’t pay attention to her much when Part of Five was on but back then she seemed so petite and I don’t understand this weight gain. She appeared to be naturally very small, albeit with pretty big jugs, but short, and naturally slender. I just can’t wrap my head around how her frame suits this kind of weight gain.

  38. hairball says:

    Her hair is beautiful.

  39. JoGirl310 says:

    Party of Five ended more than a decade ago, and I think she looks pretty darn good considering! However, she does need a stylist, stat.

  40. junk573r says:

    I am the exact same size I was a decade ago. I don’t think that really has anything to do with it…

  41. filthycute says:

    Except for the shoes with the toe-verhang, I think she looks comfortable and cute. Love the purse, too. It’s bold and fun.

    Give the girl a break — she isn’t a skeeze or a crackhead a la Hudgens/Lohan.

  42. escapee says:

    The good news is if she is attacked she could use her purse as a weapon. The bad news is she would have trouble running away with half of her foot not actually being in her shoe (that looks like it would kill on the pinky toe).

  43. Kallan says:

    Yep – like Jennifer (#24) and FilthyCute (#41) I gotta agree about the icky ‘toe hang’ thing. That can’t be comfortable! Dress is ….meh. But she still has a great smile.

  44. ordinarygirl86 says:

    I think her body is fine- she’s curvy and that’s fine with me! People act like she’s morbidly obese…

    But she needs a stylist to help her dress for her body because she should have known better to wear a plunging neckline like that when she is well endowed breast wise. Also I think if this were a maxi dress it wouldn’t be so tentlike. Like someone else said the real tragedy is the matchy matchy matchy-ness in the bag and shoes is rather juvenile.

  45. Confuzzle says:

    No. Just no.

  46. Kiska says:

    No…She needs more shape to her clothing or else she looks 20lbs heavier than she really is.

  47. sarah says:

    I think she should have followed the Simpson dress rule:

    If Jessica Simpson would wear that dress, you shouldn’t.

  48. dread pirate cuervo says:

    This is a ‘no’ but I must commend her on the matchy-matchy of the dress, bag, & shoes. The shoes are cute, but not without skinny ankles. I don’t have them, either, but I know to pass up hot shoes that are going to make my legs look like sausages.

  49. CB Rawks says:

    The hideous bag matches the hideous shoes, with that little periwinkle stripe. Blech. 🙂
    See it’s important to tie all that hideousness together.

  50. manda says:

    she’s so dumb. she should have just stayed wherever she was from and become a school teacher. she’d very likely be married with babies if she had.

  51. Kat says:

    A decent bra and a different purse, and this outfit wouldn’t have been the shocker it is. Love the shoes, though.

  52. Isa says:

    I don’t think anyone is saying that she is morbidly obsese or fat but that her outfit makes her appear heavier than she actually is.

    I can’t tell if her breasts are really sagging to her stomach or if it’s just an illusion from the dress’s waistline. I’m becoming more and more grateful that I don’t have large breasts. Plus I’m convinced that women with large breasts have to work harder to maintain their figure as they get older.

    (Note, I realize that almost ALL women and men have to work harder as we age, but I think women with larger breasts have to work especially hard. This is just a theory I’ve put together from observation and it’s very likely that I’m wrong.)

  53. Kloops says:

    Stylistically, everything is wrong. Wrong cut, draping, colour blocking, length, bag, support
    AND to add inault to injury it’s very matchy-matchy. She’s got a great body but this outfit isn’t doing her any favors.

  54. jemshoes says:

    My own sense of “fashion” is fairly tragic because I always emphasize comfort over style, so I’ll be true to form and just say that JLH looks “comfortable” in that dress! 😀

  55. Tara says:

    “Hon, keep the car running. I’m just gonna run into K-Mart right quick and grab a dress for this weekend. K. Bye.”

    I love some JLH but something tells me as soon as she walked out of the house in this fail she regretted it. “Aw, damn. Well, I already set the alarm…screw it.” But THANK you for not filling your face with the Tyson chicke nugget brand Botox fillers!

  56. Wicked SteppMom says:

    I have 3 words to describe this dress: Patio table umbrella.

  57. Micki says:

    Personally I preffer floatier dresses. The spandex-y Kim Kardashian type of outfit seems always trashy, regardless the body.
    But it’s the wrong type of floaty, the wrong lenght and doesn’t do anything for her. Correction – it makes her look size 4 instead of 2 (or has she put on weight?)

  58. Hollowdoll says:

    I am surprised to say I actually like the shoes. *confused*

  59. yes, yes, I would says:

    I actually think the boobs wouldn’t look so bad bra-less if the top of the dress fitted better, maybe a little tighter and not such a deep v-neck. Overall, the dress feels heavy and looks ill fitting everywhere.

  60. yes, yes, I would says:


    I like the shoes too, but that’s it.

  61. original kate says:

    FAIL. if this dress were a maxi, with less material, and she had support for her boobs and cute flat sandals she would look sweet. there is no hope for that bag, however.

  62. gg says:

    Terrible dress!
    Painful purse!
    J’ADORE le shoes though! <3

    😆 @ “Sue – … if you have big girls you can’t go free boobing it.”

    :high fives Sue and Wickedstepmom:

  63. Stephanie says:

    This look is terrible. Really, really terrible. I think she should take her money and disappear for a while.

  64. Lena says:

    I think J. Love rocked it… again. I like that it’s not as femme a look as I’ve seen her wear in the glossies. We were in the same dance class a long time ago before I moved away from L.A., and she’s so beautiful and nice in real life!!! The purse is very L.A. Photos don’t do her justice.