Winona Ryder shows off her long hair, cute LBD at TIFF: lovely or terrified?

When we last left Winona Ryder, she was looking scared to death in Venice, like she was searching the crowd for a team of Winona-specific predators. She was also making many of us nostalgic for the days when Winona was a big deal, when she was the hottest thing around, and all of us wanted to look like her. Well, Winona is now 40 years old (vampire!!) and she’s aiming for a steady career comeback – and she’s doing it the right way, I think, through smaller films and supporting parts. These are photos of Winona promoting The Iceman (same film she was working in Venice) with Chris Evans, Ray Liotta and my murder-eyed crush, Michael Shannon.

I can’t find the designer IDs for either of the dresses that Winona wore at TIFF. She chose a lovely green, buttony dress for the photo call, and a puffy-skirted LBD for the TIFF premiere. She also kept her hair down for the photo call – look how long her hair is these days! Remember when she kept it short? Remember how all of the girls wished they could pull off Winona’s spiky little ‘do? I remember that. Anyway, Winona doesn’t look as terrified in these photos, but she still seems kind of overwhelmed.

I had no idea Chris Evans was in this film. The Iceman has a great cast!

Photos courtesy of WENN.

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85 Responses to “Winona Ryder shows off her long hair, cute LBD at TIFF: lovely or terrified?”

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  1. Bite me aka aniston says:

    Skin looks good… But Wino definitely looks her age

  2. NYC_girl says:

    Ray Liotta!! Don’t think I could choose between him and Capt America. Winona needs to take a deep breath and relax a bit. She looks freaked out.

    • V4Real says:

      I would be freaked out too if I was standing around all those hot men. Chris Evans is delicious. Word to the writer of this article; Chris Evans plays the Ice Man mentor in the film: a role that was first offered to James Franco.

  3. Jayna says:

    A relative, a co-worker and a sister of someone I know all had their eyes done when only like late 30s, 40, and all of them had this hard, startled look for like a year or two. The sister admitted it made her look like that and realized she had done her eyes too young.

    • Jenny says:

      A co-worker of mine had her eyes done (we all felt it was a bad job since everyone knew it) and she had that same startled look. Every time I looked at her during meetings, I always felt like widening my eyes too as the look was so harsh. It got to where I could not look at her or I would have embarrassed her and myself.

  4. pretty says:

    she looks like she is scared out of her mind 24/7… those eyes..not a good job

    • Belly says:

      Has she had them over-lifted or something? They look ready to shoot out of her head and roll across the carpet.

  5. Kaye says:

    So is the consensus a bad eye job vs. horrible anxiety?

    • Jayna says:

      Absolutely. When you are young (30s, early 40s) and don’t have a lot of creppy skin over your eyes, just a little, and get an eye job, it pulls probably a little too much skin or snips it, whatever it does, and you get that deer in the headlights look, startled. My friend’s sister looked older, not younger, when she got hers done because it gave her a harder look, and she admitted later, she had a couple of friends in Atlanta suburbia do it and she recognized the same look to them for quite a while, a couple of years, and that’s when she realized what she looked like. Of course, we all already knew she looked hard, just would never say anything. And still photos tend to show it up even worse than in real life just looking at them while talking.

    • Jen says:

      She got the eyes done a few years ago and has – sadly – looked like this ever since. Not good.

    • QQ says:

      Tha’s what Im Thinking!! Im all: Is No One gonna say that this Bitch has A Ramona from RHONY BAD BAD Crazy Eye Job?!? Cause it just looks like is not panic Is more like “HALP!, I Botoxed and cant Close my eyes, or emote or… Anything!”

    • ZenB!tch says:

      Horrible eye job but yes she is on something, her eyes look crazier than Bradley Cooper’s did last week when everyone said he was on something.

      Her nose is off too and she looks underweight.

  6. KellyinSeattle says:

    I love Wynona but she’s had terrible work done on her eyes. If she has an anxiety disorder, that would be different…I take meds for that but it doesn’t make me look like that. She is so little! Love Ray Liotta, and the pic of the other guy is cute. With her hair down, she kind of reminds me of someone ??? Salma Hayek?

    • Mimi says:

      Oh you nailed it; she looks like a teeny tiny petrified Salma!

    • KellyinSeattle says:

      Sorry, Winona, not Wynona…

    • ZenB!tch says:

      I’m on all sorts of things for anxiety. I actually checked the mirror to see what my eyes looked like when I took them last week after the Bradley Cooper thread. I look fine. She looks worse than Bradley did and her eyes are brown which hides the pupil some. She looks like a deer with a bad eye job in headlights.

  7. nate says:

    is it just me or does her forehead look botox-y?

  8. PinkPunk says:

    She just looks crazy as hell IMO

  9. spinner says:

    I don’t think she looks good at all. She’s had a really bad eye job & what are all those little tucks along her cheekbones. Bad plastic surgery. Sad.

  10. Just me says:

    I’m sorry, but no. Winona has always taken good care of her skin and hasn’t been a big sun worshiper. She stays out of the sun. If you look at the closeups, she looks age appropriate for someone her age who has taken care of herself. I’m not seeing any plastic surgery here.

    BTW, I’m rooting for a Wino comeback. I loved her in the 90s, and I still love her today.

  11. Mimi says:

    In that first pic her head looks ginormous compared to her body. I don’t know why, but I was literally heartbroken when she f-cked up and I’ve never ever forgiven her. (I know that sounds creepy but I grew up in the same town as her & she was our heroine.)

    • kay says:

      I’m going to go out on a limb here, and say that I bet Winona could give a rat’s fat ass if you forgive her or not.

      • Mimi says:

        Ha! Of course not, how astute of you.

      • Annie says:

        Hmmmm, probably doesn’t give a rats ass about you either! Or anyone on this blog- thanks for pointing out the obvious.

      • Laura J says:

        All snark aside, Winona did fall pretty hard in a lot of people’s eyes. She wasn’t supposed to be *that* girl, you know? She was the ingenue and an icon for the underdog for a lot of fans, especially to those in NorCal who were familiar with her efforts in the Polly Klaas case. It didn’t help that she went on to state she felt “no guilt” for her arrest, blamed it on pill addiction, and then continued to abuse drugs. (Oh and you know Goopy just delighted in her humiliation!) But whatever, she’s human and makes mistakes like the rest of us. I’ll always be a fan; Wino Forever.
        Oh and I think she looks lovely here, perhaps a bit thin & startled, but she’s still got it.

    • Zobeth says:

      @ Mimi -I grew up with Nona so you must be from P-town…in fact went to school with her for awhile and yes she did look like this 27+ years ago…always willowy with those big doe eyes. I just became mad at her when she started dating Johnny Depp because when I was a senior I had a poster of him on my wall damn it!

  12. carrie says:

    why am i thinking BLACK SWAN’s lead character when i see her botoxed face?

  13. Aria says:

    It’s so strange watching her with long hair, which I have to admit I love it!!!!!!!

    My only complaint is the green dress. Plain awful! She can do so much better but she is my forever girlcrush so she is forgiven. I am a “winohard”

    • Chicagogurl17 says:

      I agree about the hair. It’s nice to see no extensions and the cut suits her. I love the green dress but not on her. It’s a bit older.

  14. kibbles says:

    Did she really have an eye job or is it just botox? Or perhaps both? Why do beautiful people mess with their looks? A few wrinkles would look so much better than botched plastic surgery. She also needs to gain 15 pounds. She looks so frail and whatever she has done to her eyes makes her look really crazy.

  15. Tiffany27 says:

    Yeah she looks scared as hell, but I’m glad to see Winona. I can’t wait for this movie btw. I love Michael Shannon’s creepy as hell face. Also, my boo Chris Evans!!

  16. V4Real says:

    Third picture down, she has that deer in headlights look. BTW, once again, Oh Chris Evans what a tasty treat you are.

  17. HadleyB says:

    she looks uncomfy, she has a similar stance like Britney does — with the shoulders .. they would look so much better if they could relax but I am sure it’s hard if you suffer anxiety etc.

  18. Nancy says:

    She looks beautiful with her long hair down in the 2nd picture.

  19. Cam S says:

    Gosh Ray Liotta makes me hot STILL TO THIS DAY. They don’t make em like that anymore…

  20. km says:

    I’m just now thirty. I used to make my baby sitter bring over her VHS of Beetlejuice or there would be all kinds of hell to pay. It’s odd to me to see Lydia aging, especially since I haven’t seen Winona in so long. Guess I’ll have to start getting used to it.

  21. tmbg says:

    That is some Marcia Cross Botox if I’ve ever seen some. I don’t understand why these Hollywood stars can’t find a conservative plastic surgeon. Do they ask for it to be so severe?

  22. francesca1 says:

    She could have a thyroid issue. Bulging eyes are a symptom and she is sooo skinny.

  23. bns says:

    Love her so much.

    I always immediately click when I see news about her. Like a moth to a flame.

  24. Maritza says:

    Winona has the crazy eyes look.

  25. Minky says:

    GAH! I love her!! She looks so beautiful, especially in that green dress in the full cast photo.

    Is it just me or does she look happier and more grounded while photo’d with Chris Evans? 😉 I’d be down for that pairing.

    I know she’s always had crazy eyes, but she does look a little ‘toxed. She’s beautiful regardless, though!! Glad to see her back around again.

  26. PrettyTarheel says:

    It’s not her eyes that make me think she’s scared. She perpetually looks like a deer in the headlights. It’s the tension in her neck! I can practically count tendons and ligaments. When she has someone right next to her, her neck relaxes a bit-it’s like she’s scared to pose alone.

  27. Megan says:

    What’s with the crazy coke eyes.

  28. Kerfuffles says:

    I don’t think it’s an eye job or Botox that makes her eyes look that way. It’s not that they look pulled to tight. It’s the actual expression of her EYEBALLS–she looks scared & anxious down to her soul; it’s in her body language, too.

    She’s obviously a girl with some issues. When she was arrested for shoplifting the most shocking thing to me wasn’t the stealing but ALL the drugs she had on her & the type of drugs they were. Along with a bunch of other prescription pain meds, she was carrying around a syringe and liquid Demerol, which is just CRAZY.

    Hopefully, she has such scared looking eyes now because she’s actually dealing with her anxiety & emotional issues and not blocking them out with pain meds & Valium.

    I hope she can make a successful comeback. She seems so fragile.

  29. stinky says:

    ok, no ones said it so i will. TOENAIL POLISH IS YOUR FRIEND!?? How can she wear that dress and those shoes and not wear polish??? fail fail FAIL. I love her tho…permanent fan. she’s just too cute.

    • Gia says:

      Are women required to polish their toenails if they dare to expose their feet in public?

      • ZenB!tch says:

        I wear toenail polish probably 99.999% of the time but I thought the rule was as long as your toes are groomed and clean looking no polish was fine. It’s chipped polish that makes me cringe.

  30. silvermistie says:

    who is the guy on the right in the group photo?? looks soooo familiar but name just won’t come to mind!

  31. D1 says:

    I think she looks great. Of course, she wonderfully portrayed Veronica Sawyer in Heathers, so as far as I’m concerned, she has the right to dress up in trash bag and clown shoes 24/7 if she feels like it.

  32. d says:

    I can’t be bitchy about Winona. I’ve always liked her and still do and I think she got smacked down way way too much in H-wood for what happened. Maybe there was more to the story about her (e.g., being difficult, whatever) and I can also believe that whole mess lead to severe anxiety problems. Although I think Britney Spears makes a better case of what someone who’s got that look like. Whatever. I’m rooting for both to have a happy, healthy, and productive life.

    • Irishae says:

      Her shoplifting scandal came before the days of Us Weekly and gossip sites–it was such a huge deal when it happened that I don’t think she has ever really recovered. She got a lot of shit for it, undeservedly. I think it’s a combo of bad eye work and fear of being scrutinized.

  33. skuddles says:

    Is it me or does Winona have some mighty big pupils in these pics? Aside from that, I think she looks lovely; she appears to be aging nicely.

  34. lafairy says:

    Beside the terrified look in her eyes I think she looks fantastic,pretty and very youthful! I can’t believe she is 40!!
    That’s how I want to look at 40!
    She looks really fresh and I love her bambi look, she has always been a bit odd and it’s a quality I like about her, after all these years in the industry she managed to have retained spontaneity!

  35. Kate says:

    Madeline Stowe meets Susan Lucci.

    She really doesn’t look like herself anymore.

  36. mk yarwood says:

    I want that green dress

  37. Darth says:

    I’ve always preferred pixie cut Winona to long haired Winona, especially since she most often just pulls her hair back lately. However, I DO really like the long hair draped down on one side look that she’s giving us in the green dress! It’s a new style for her and it brings out her sexiness and flatters her face much better than the homely tight bun or ponytail does. And I have to say she still has the most amazing bone structure of practically anyone.
    Winona Forever 🙂

  38. ZenB!tch says:

    OK she is beyond skinny. She looks as flat as Goop in that black dress and Wino was never flat. She always had a rockin’ figure. Bring back the boobs!

  39. LeslieM says:

    She’s known for her shorter hair. I don’t think this looks right for her. She was beautiful before.

  40. Sugar says:

    she is a tiny little creature isn’t she! I have always has a place in my heart for her-I can’t help but think how affected she was by Polly Klaas & how she stepped up for her hometown to help anyway she knew how.
    I hope her second time around career in HW treats her kind:)

  41. doe eyed says:

    I think being doe-eyed is so beautiful when you’re young, but not a good look when you get older… look at Audrey Tautau, Luke Haas, etc. It’s like you don’t want your eyes to stand out that much when you’re older.

  42. Raynor says:

    I adore that green, diagonally-buttoned dress.

    I don’t know if it’s botox or an eye job, or she’s generally terrified (I know I would be!), but otherwise she looks fantastic. I’m really pulling for her!

  43. Giggy says:

    I love her but she’s had a fair amount of plastic surgery and a whole lot of botox. She’s in her mid 40s. At the very least, she should have soft natural lines around her eyes – even if she was never in the sun. A lot of actresses do a little too much and look startled and pulled for a year or two and then their faces settle down. I hope Winona’s adjusts accordingly and that she lays off the botox, fillers, etc. for a while.

  44. Bobby sue says:

    Couple things:

    She looks TINY next to all the men in that one photo call shot!
    I actually think she looks better now as she ages (especially close-up shot with green dress) but the deer-in-head-lights must be Botox, right??
    Lastly, if you couldn’t find designer info I know she just about always wears vintage couture for big events, her fave shop being Decades in LA.

  45. Bobby sue says:

    Moreover, I think she’s aged much better and more subtly than her arch nem Gwennie. Gwyneth is always lauding her cleanses and skin this and that and imo her hair and face look fried by comparison!
    Byt Gwyn has 2 kids so I’ll give her that.

  46. Dig the photos of Winona’s long hair. Thanks for posting!

  47. I think it is anxiety. She has looked like this on the red carpet for the last 10-15 years, but always looks normal in movies.

  48. angela says:

    how do u try and contact winona? i met her on the set of beetlejuice yrs ago. i helped with that movie. never geting any credit. a minor when it began. she really is a nice chick! angela