A barely-recognizable Jessica Simpson stepped out in NYC to receive an Icon Award

Over the summer, Jessica Simpson did a big exclusive with Bustle – an editorial and an interview. I hadn’t seen new photos of her in a while and I was startled by how different she looked in those pics. She said, in the interview, that she’s not on Ozempic, but her face tells a different story. Well, Jessica stepped out this week in New York, and here are some photos of her appearance. She was honored at Footwear News’ Annual Achievement Awards and she received the Icon Award for her successful footwear and clothing company.

I’m not sure how much I want to get into it or try to figure out what Jessica has done to herself. After her third child and after Jessica got sober, she steadily lost weight and that changed her face. But… yeah, I also think she’s gotten some work done and it’s not good quality work either. She was always so beautiful, but it’s actually on-brand for Jess that she sort of looks like a Real Housewife now.

Professionally, Jessica is seemingly in a good place, so at least there’s that. She and her mother have basically bought back full control of Jessica’s eponymous clothing line and brand, and Jessica is maybe/probably still in debt up to her eyeballs. It honestly feels pretty tenuous, so I hope everything works out in the end.

Photos courtesy of Backgrid.

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80 Responses to “A barely-recognizable Jessica Simpson stepped out in NYC to receive an Icon Award”

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  1. Abby says:

    I have followed Jessica’s trajectory for years and years, since the Newlyweds days. I’m rooting for her to be healthy, happy and well.

    Every time I’ve seen photos of her over the last year (?) I’ve been shocked at how she doesn’t look like herself anymore. And that she’s very thin, even just in photos. She actually looks healthier here than she has in any photos she’s posted on her accounts in a while.

    Hopefully she’s ok and doing well. I’m glad they got that business back – after reading her book it’s apparent she and her mom were really proud of that company. And I do love their shoes and sunglasses!

    • SophieJara says:

      To me what’s off most in these photos is her (lack of) smile. I feel like her wide dazzling smile is a really iconic part of her look? And she’s not smiling at all here, maybe she can’t smile right now, but I hope she goes back to that. She doesn’t need to be trying to pose like a Kardashian, it doesn’t even look good when they do it.

      • teehee says:

        It looks like she CANT smile.

      • TheFarmer'sWife says:

        She looks like she’s in a lot of physical pain!

      • Mustang Sally says:

        Yes! In the bottom photo of her and her mom, she looks like she is unable to smile (like there’s too much filler in her upper cheeks or her face is frozen). Her lips (to me) look like they have more filler. Besides buccal fat removal, is there filler or a procedure for the jawline? Her jawline looks very square and angular.

    • HufflepuffLizLemon says:

      I love their jeans! I’m wearing a pair right now (with a cable knit sweater that Lainey recommended; apparently I’m a sucker for celebrities and recommendations). They fit great, they’re fashionable, and they have held up well so far. I fell down the driveway and expected the knees to be shredded (lord knows my legs were a mess) but the denim doesn’t even show a mark.

    • NotSoSocialB says:

      She has had buccal fat removal. Too bad. It won’t age well as her skin loses elasticity.

      • Chica says:

        Buccal fat removal ages people. See Margot Robbie.

      • nisa says:

        She was a completely stunning woman and looks so different – agree that it isn’t just weight loss. As a (formerly) round-faced lady of a certain age, I will never understand this procedure. You are so grateful for that fullness as you age! I predict a surge in buccal injectables or grafting (whatever the technical term is) in a few years, and hopefully the operation itself falls out of fashion. She’s overcome so much, I hope she’s happy with what she sees in the mirror now and stops tweaking.

      • DouchesOfCambridge says:

        I find all the ozempic faces look the same – I find looking at thes epictures and sharon osbourne and jessica simpson look the same – something’s not right.

    • Campbell says:

      Something is giving her face a masculine look and I can’t figure out what it is.

      • goofpuff says:

        It’s the buccal fat removal. It turned her usually rounder cherubic face all to hard angles. And her inability to do her trademark smile doesn’t help either.

      • jbones says:

        Also, I think her forehead dropped? Is that a thing? Her brow bone looks very low and pronounced.

  2. HollyGolightly says:

    If you read the comments on any of her Instagram photos, it’s AWFUL how cruel people feel the need to be. I don’t understand people. She’s been open about all of her insecurities about her body and being scrutinized. I don’t get why people need to be so hurtful in comments she’ll likely see.

    • Bettyrose says:

      I’ve always felt sympathetic towards Jessica. At one point, even “legitimate” news sources like CNN were regularly reporting on her weight struggles. We all need to be concerned about that level of body policing because it impacts all of us. That said, I wouldn’t even be certain this was her if I saw the photos out of context.

    • escondista says:

      She doesn’t have to have a public Instagram. ALL of the people featured on this site have more power, agency, time, opportunity, and money than all of us (likely combined) and don’t have to engage in public life if they choose not to.

  3. JaneS says:

    Lip fillers, far too much.
    Has she had buccal fat removal too?
    She looks really rough in these photos.

    Money problems?
    I thought her clothes/shoe line made her a multi-millionaire.

    • mblabes says:

      seems like buccal fat removal versus ozempic. and yeah, too many lip fillers.

    • manda says:

      She HAS to have had the buccal fat removed, right?

    • pollyv says:

      It does look like buccal fat removal and filler in the jaw line to make it much more square which I always think is too masculine looking.

      • sparrow says:

        Agree with you, pollyv. And it has left her face at such odds with her bosomy (does anyone else say that anymore!) body. I know those breasts are likely fake, but she’s bought herself a curvy body with a scrawny face on top. When I see this kind of thing I think, that is a lost person. I don’t know anything about her, but she looks sad. And the way she’s holding her mouth, like she’s ready for sex whenever. Lost.

    • GrnieWnie says:

      Lip fillers are WAY too much.

      In terms of buccal fat, I think we should remember that most women lose fat on their face as they age. I’d say she probably had too much cheek filler.

      She had a tummy tuck after her second child (which she talked about publicly) and then got pregnant again…I always wonder how that was even possible. If you cut off a bunch of skin/fat, then stretch it out again…that gives me the shivers thinking about how uncomfortable it could be.

      I saw someone on TikTok saying you shouldn’t comment on people’s plastic surgery as it’s akin to commenting on someone’s tattoos. I get the point, but I disagree: cosmetic surgery comes with real risks. Lest we forget, Kanye West’s mother died getting liposuction. It comes with risks to your health and can easily be botched. So I don’t think we, as a society, should be so readily accepting of plastic surgery/strictly cosmetic enhancements. I think we’d be better off turning our attention to simply accepting a natural, “imperfect” appearance.

      • sparrow says:

        I have this thought, as well. We don’t comment on coloured hair and make up these days. My grandma did, however. She was very anti dyed hair, thinking women should just go grey and, oh, what vanity. So why haven’t we moved on with cosmetic surgeries; why do they remain so noteworthy? I think it’s because procedures are seen as cheating in some way, much more so than temporary colour and make up. Again, I’m with you on this – It is important to talk about them rather than ignore them. I want my kids to know that people have paid to get a certain look; it’s not normal to have a body shape so at odds with, in many cases, a person’s low body weight. I don’t want my kids to internalise a feeling of inadequacy about shape, weight, and how we age. That’s why I hate the amount of photoshopping someone like Kate gets – it hides what unnatural body weight does to people (in her case, hair and skin deterioration).

  4. escondista says:

    The weight loss, frozen forehead, and filled lips looks scary. As an Xennial i have a theory that white people whose heyday was in like 2004 never want to leave that era of like streaky blonde hair, low-rise-jean-skin-showing sexuality, tanning beds with the playboy bunny sticker, and an obsession with being skinny. When i look back, its such a gross era to me…those popular kids somehow looked sweaty and dry at the same time with overly lined eyes and a dirty orange skin color.

    • Bettyrose says:

      Bwhahahaha! You’re killing me with this description, and no lies detected. Paris Hilton would like a word, though. 🤣

      • escondista says:

        I totally wanted to be them at the time! “One time I saw Cady Heron wearing army pants and flip flops. So I bought army pants and flip flops” – totally me. I’m just glad i was too poor for tanning beds. I kind of admire Paris for finding a platform to share her story in order to help others.

    • molly says:

      I am feeling VERY attacked right now, lol.

      It’s a shame that Jessica seems so drawn to that look because while, yes, that era it was her professional heyday, the media was absolutely brutal to everything about her.

      If it were me, I’d cut a brunette bob, move to the mountains, happily eat carbs, and introduce myself as Jess Johnson. I’d never give the tabloids the satisfaction of seeing my millionaire face again.

      • bettyrose says:

        @Molly – At the risk of suggesting women should hide away past their expiration date, which seems to be a popular theme in Hollywood, I often wonder why many celebs don’t do just what you’ve described. The ones that disappear and only emerge for important events seem happier. Sandra Bullock wrote the book on dodging intrusive press while maintaining her career.

      • molly says:

        @bettyrose- Sandra Bullock hid a BABY! For months!! During an Oscar campaign!!!

        I don’t assume anyone’s life is perfect, but you’re right, when celebs stay largely out of the spotlight, they sure seems happier for it.

    • Flamingo says:

      omg im so embarrased but I had the stripey /streaky blonde highlights circa 2004-2005. thought i looked like Kelly Clarkson lol. CRINGE!

    • Chaine says:

      Y’all must not live in the south. Every other forty-something woman still has the streaked blonde hair.

  5. Alicky says:

    Still not sure how she managed to lose all those millions…? Hate to say it, but she’s looking like Melania here.

    • Betsy says:

      I was thinking Ivanka. Same thing though, really. Either they share a surgeon or their surgeons share an aesthetic.

    • SarahCS says:

      I thought Kim Zzzzz-something, the real housewife who may or may not be getting a divorce and whose adult daughters look like clones.

  6. It’s like her poor face can’t move.

  7. Kristen from MA says:

    She still can’t close her mouth. That open-lip face is supposed to look sexy, but it just looks stupid.

  8. DeltaJuliet says:

    If you hadn’t told me I would have thought it was Kim Zoliak.

  9. Nicole says:

    I truly wish her well. I do think she’s too thin. As long as she’s happy and healthy that’s all that matters.

  10. wordnerd says:

    I don’t believe much of what Jessica says about her personal life. She often seems out of it in interviews in the past few years (though I hope she’s still sober) and her weight loss explanations echo Mindy Kaling’s. It’s hard to trust someone who’s selling a questionable image.

  11. Justpassingby says:

    Jessica Simpson and Zac Efron: Two individuals born with perfect genes and perfect physiques, but apparently unable to love whom they saw in the mirror due to significant BDD. How tragic!

  12. Kaye says:

    I too have always had a soft spot for her, but now she looks so harsh.

  13. Amy Bee says:

    She looks like she can’t close her mouth. This is bad.

  14. lucy2 says:

    Her book was way more interesting that I expected, and I ended it wishing her well, and being glad I’ve never had to face the scrutiny that she has.
    She certainly does look different, and doesn’t look very happy, but hopefully she is.

  15. girl_ninja says:

    Is Jessica in debt? Her shoe line alone is printing money for her. She is a very, very wealthy. Even with whatever she has done to her face, I still think she is gorgeous.

  16. D says:

    Part of the issue is that she looks exhausted. No amount of makeup can hide that, I guess. She’s very thin and I don’t think Jessica is naturally super skinny and it’s hard and unpleasant for her to be at this size. She talked about it as far back as Newlyweds when she was shooting Dukes of Hazard and basically had to starve herself and workout every day. She was miserable but she looked amazing. So if she isn’t using a weight loss drug and is just working out crazy hard and limiting calories and carbs she just may not feel great.

  17. Chantale says:

    It is amazing that the brunette lady next to her, who I assume is older than Jessica looks much younger. This picture of Jessica is not flattering.

    • molly says:

      That’s her MOTHER!

      Tina does look great though. Her parents both seem to have found contentment now that they’re separate and living their best, authentic lives. Same with her sister, hugging it up with the wholeass Ross family. It’s a shame that Jessica doesn’t appear to have the same peace and happiness as the others.

    • Erin says:

      I was thinking the same thing, that’s her mom and she looks younger than Jessica. Too many fillers always make younger women automatically look like older women trying to look younger, they don’t actually look younger IMO.

  18. M says:

    Her face is very square and reads “masculine” to me. It wasn’t like that before. Bless her heart.

  19. tatannelise says:

    I think she looks very nice. It’s a bit fuller lip than I would do, but I know numerous women who feel better with a very “puffy pout” even though they are aware it doesn’t look all-natural. Otherwise, she doesn’t look all that different to me, and people should just lay off and let her live her best life.

  20. Grant says:

    As a gay who came of age in the early aughts, I will always have a soft spot for Jessica and want her to succeed. I think she’s definitely lost a significant amount of weight — it’s likely in part due to going sober, I remember her mentioning that she liked whisky and bourbon, which are both calorically dense. I don’t think she looks TOO different but she’s definitely got a lot of filler in her lips.

    Good for her for receiving the Icon Award. Her shoes are great and budget friendly.

    • Kate says:

      I don’t think she looks that different either, although she went very heavy on the make-up, which I think is often very aging. In the spread that was posted recently, my main reaction was she looks more like her sister Ashlee as she has gotten older.

    • Agreatreckoning says:

      Jessica has always been beautiful. She is not looking like her beautiful self.imo She’s always had a great smile and face structure (losing weight doesn’t make freeze face happen).

  21. Kirsten says:

    She looks very different, but it’s almost impossible to know for sure when someone is wearing that much makeup. Adriana Lima recently got a lot of comments about crazy plastic surgery, but it you look at her in the video where she’s getting ready, she looks totally like herself when she’s not wearing makeup.

  22. Baily says:

    She looks terrible. Her face has been altered, and honestly, to me, she doesn’t look sober. I think she’s drinking again or taking opiates maybe because those keep you thin but also make you look totally out if it, and to me, that’s how she looks. Just exhausted and totally incoherent.

    • molly says:

      Completely agree. She and I are similar ages, and even those of us with full-time jobs, middleclass incomes, and cook/clean for ourselves don’t look nearly that exhausted. Especially on big, exciting nights out. She presumably has none of those factors, and she looks and sounds pretty messy these days.

    • MsIam says:

      That’s what I thought. I didn’t notice the face or figure at first, just that her eyes look really vacant. I know she’s had a rough time and I hope she is ok.

  23. Bumblebee says:

    You’ve got to have the skin of an armored car truck to survive the comments celebrity women get about…everything.

  24. Flamingo says:

    I thought it was interesting she bought back her company. I just wonder how successful it can be in the long term without the creative genius behind it. Vince Camuto passed away in 2015. He was the one that navigated the company to the sweet spot of mid-priced fast fashion the women clamored for.

    Also, if she did get her buccal fat removed from her cheeks. They took too much. I have seen a few YT videos from plastic surgeons warning people against the surgery. It may look good in the short term. To give you that contoured face. But as you age you will end up looking older and sunken in. You can’t replace buccal fat. Once it’s gone, it’s gone forever.

    • Twin Falls says:

      “I thought it was interesting she bought back her company. I just wonder how successful it can be in the long term without the creative genius behind it. “

      The little I’ve read said she mortgaged everything to buy it back. She said she’s never had to live on a budget before and was finding it difficult. I thought that didn’t sound promising from a business perspective. Her looks reflect a stressful life imo.

  25. Spenceraulait says:

    As someone who did take ozempic, i can say it changed mine and has changed all the faces of the women I did it with!! It’s crazy how a little extra weight in the face makes you look so much younger, happy and healthy. I definitely regret it

    • Andrea says:

      My doctor has suggested it for weight loss (I am overweight not diabetic). I am not sure I want to lose my looks in my face. I am working out with a personal trainer instead and getting stronger.

  26. phlyfiremama says:

    Harpo, who dis woman??

  27. Digital Unicorn says:

    I’ve always had a soft spot for her – she doesn’t look like herself and I hope that she’s in a good healthy place.

    I had forgotten that she had a very successful clothing brand that really puts everyone else’s to shame. Am in the UK so we don’t have it here but after having a look on the website I can see why it does well – its fun, colourful and trendy with affordable prices. She knows her market.

  28. J.Ferber says:

    I’ve always liked her. It’s sad what women feel forced to do to look young in Hollywood. I don’t think the rest of the country really understands how brutal the system of youth above everything else hurts women mostly, not men. I hope she lives her best life.

  29. Sophia’s Sisdeye says:

    I’ve always liked Jess and I still do, she is a sweetheart and harmless. It looks like she’s had a liquid facelift to balance out her face from likely too much weight loss. What looks not so great to me are her lips, but that’ll go down in time. It also looks like she put a little weight back on and that looks really good to me, she was looking very hollow for a while. I’m not gonna look down on any woman in Hollywood for trying to maintain their looks, LA is not for the faint of heart.

  30. AS says:

    Wow. She looks a lot older than her actual age. She looks like a fifty something year old Orange County housewives. She was so beautiful and I wish she would just let her face age naturally.

  31. ArtFossil says:

    She looks hideous. Ghoulish. Night-of-the-living-dead awful

  32. Dani says:

    Omg, she looks older than her mother. Poor Jessica.

  33. Andrea says:

    In addition to whatever is going on with her face, her makeup is terrible IMO and makes her look older. As someone said above, she looks ghoulish definitely like those too thin older ladies in their 50s and 60s.

  34. Andrea says:

    Also, can anyone explain to me why her throat looks like that??

  35. Sparkles says:

    Is her neck muscular?