Winona Ryder, 40 years old, wears all-black in Venice: lovely & nostalgic?

These are some new photos of Winona Ryder in Venice. She’s in town for the film festival, to promote her new film, The Iceman, with Ray Liotta and Michael Shannon. Incidentally, both Ray and Michael are considered to be “scary” character actors who normally play psychos and crazies… but I would hit it with both of them. I love Ray Liotta so, so much, and Michael Shannon is one of my most secret dirty-crushes. I would go to bed with either of them. Or both. AT THE SAME TIME.

Winona wore black for both the day photo call and the evening red carpet premiere. Winona wore a short, vintage LBD for the photo call, and she wore a long Dolce & Gabbana gown for the premiere. I like both looks, honestly. I can remember a time when Winona was The It Girl and she was the top, top Fashion Girl and everyone wanted to wear what Winona was wearing and look just like Winona. But that time has passed, and you can tell that she still loves fashion, but she’s 40 years old (VAMPIRE!!!) and she doesn’t need to be wearing the “latest style” at this point. She knows what looks good on her (for the most part), and she looks classic and pretty. The Dolce gown isn’t spectacular or anything… but it’s not a failure either.

I do think Winona looks very uncomfortable, though. In most of the photo call pics where she’s standing alone, her eyes look kind of crazy, like she’s a cornered animal. It’s been a while for her… hopefully, she’ll get the hang of it.

Photos courtesy of WENN.

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110 Responses to “Winona Ryder, 40 years old, wears all-black in Venice: lovely & nostalgic?”

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  1. judyjudy says:

    Winona Forever!

    • zinjojo says:

      Exactly my thought when reading the post. I really hope she makes a comeback!

      • Genevieve says:

        I think she looks simply, elegantly, lovely.

        She always managed to nail the Gen X’er/ Audrey Hepburn thing beautifully. I will be looking forward to her “second act”.

  2. duncecap says:

    oh, i miss her… I hear she was a bright spot in Black Swan but I will never see that movie. I might see this one

    • jc126 says:

      She wasn’t that great.

      I’ll wait for the flames on this one – I think Winona Ryder is kind of a sad figure now. She had all these different guys in love with her at various times, and they all settled down, more or less, and she’s turned out to be a pill popping, shoplifting actress with a struggling career following legal troubles for the above. And, frankly, a woman with so many guys in her past probably isn’t fond of being alone, either.

      • Jess says:

        She used to exude youth and confidence and a girlish sexy charm. Now she looks frail and scared of her own shadow. She’s not the Winona of old. It’s very Britney-esque… the lights have gone out, and that magic they once had is gone.

      • valleymiss says:

        Ah yes, ol’ Wanna Ride-Her. Lol She was following around every It Boy of every alt rock band during the 90s. Then she shoplifted and was never heard from again, it seemed. I’ll never forget going to see Pete Yorn about a month after the shoplifting. He is this alterna-dude who never quite got the career he was supposed to have. Anyway, Winona had gone after him and then the shoplifting charge came up. When I saw him in LA, he dedicated “Shoplifters of the World Unite” from Morissey (or the Smiths?) to her. It was pretty funny.

        She has a slammin’ bod (petite with a nice rack) and she has gorgeous skin, but that eye job/perma-scared look she’s got is awful. She could still pass for early 30s, I think. She’ll always hold a place in my heart as Veronica Sawyer! She was everywhere during the late 80s and all through the 90s. Remember how adorable she was in “Lucas” with Corey Haim?

      • Jo 'Mama' Besser says:

        The Smiths.

      • bns says:

        Johnny Depp is just as messed up as she is, he’s just better at hiding it. And I heard that she’s in a relationship with someone who works for Sony (?).

  3. dorothy says:

    She looks beautiful.

  4. Zimmer says:

    Wouldn’t hit either, but I like their movies. Girl looks scared s…less.

  5. Answer says:

    She looks weird, like she needs to go steal some candy are something.

  6. Tania says:

    I think she’s aged incredibly well. Apart from looking a little stunned from her Botox, it doesn’t really look like she’s messed with her face.

    • brin says:

      I agree.

    • Rory says:

      It looks like she has messed with her nose. I don’t know why, it was perfect before now it’s too pointy and has one of those funny balls on the tip. Otherwise she looks good.

      • kimmy says:

        i think she has messed with her nose! its so sharp and pointy and i can’t remember it ever being like that. maybe gaining a few pounds would make her features less harsh? i don’t know, but i WANT her to be on top again. i had a major girl crush on her growing up. WINONA FOREVER!

      • Jo 'Mama' Besser says:

        I was just about to say that. I wonder if it’s recent.

    • Lucinda says:

      That scared look is more than her eyes. It’s her who posture. Her shoulders look tense, her arms are in front of her in every picture. This is not a relaxed woman.

      I’ve always loved Winona. I wouldn’t be surprised if her breakdown/shoplifting was related to mental illness as well. If it had happened 10 years later, the judge wouldn’t have been nearly as hard on her. Look at Lohan. I think he did her a favor though.

      I hope she can come back on her terms whatever those may be. She was good in the Black Swan but her part was small so you didn’t really see what she is fully capable of.

    • erika says:

      yeah yeah yeah! I don’t have to go on a bitch-rampage about looking ‘haggard’ at 40 like our friend HoLO (who does NOT look 40 she looks like a cryptkeeper)

      see? 40, 90 it’s all about how you take care of yourself and good GENES.

      she looks great, whatever.

    • Pandy says:

      You’re probably right re stunned with botox. She looks scary in the eyes and she could use a few pounds. Great skin though, wow.

  7. cynicalsmirk says:

    That’s a shame, duncecap. It was an extremely good movie.

  8. Waldemar says:

    She has lost some weight.

    Hope her career can revive. She is a great actress and never deserved the fallout after her shoplifting ordeal.

    • Jo 'Mama' Besser says:

      If she had to have a fall, The Age Of Innocence seems like a possible culprit.

  9. RocketMerry says:

    She looks amazing! Good for her. I like her.

  10. Abby says:

    She looks beautiful. And terrified.

  11. Kimlee says:

    She looks scared and uncomfortable in every picture whether she was standing alone or with the other actors.

    • Audrey says:

      Agreed – I feel bad for her just looking at the photos. She looks like she’s terrified and does not want to be there.

  12. FrenchT says:

    She looks very good and perhaps a little too thin. Her gown doesn’t fit well. It looks like it does not zip all the way and also the seam is not lying straight.

  13. Jen says:

    The “cornered animal” look can’t be helped . . . she messed up her face with a bad brow lift and now that look is permanent. Sad – she was so pretty.

  14. Bad Irene says:

    Love her soooo much, sat through Dracula several times just for her and Gary Oldman, hangs head in shame 🙁

  15. Eve says:

    Mah husband Chris Evans is in this movie as well.

  16. RHONYC says:

    i love the pic with Liotta & Shannon.

    it’s crazy on crack.

    warms my heart. Hmmmm. 😉

  17. mel says:

    I use to just LOVE her…she was so gorgeous and just cool in a way most of aspired to be…glad she is coming back to making movies. She looks great…leave her alone!!!! :):)

  18. DianeP says:

    Wino Forever! I adored her in “Little Women” — the ending with Gabriel Byrne is gorgeous.

    • Natasha says:

      I love Little Women! She was great in it and what an all star cast, I have to watch it every time it is on TV

    • minimi says:

      I will always remember her in that movie. I loved to read the book when I was a kid, and then I loved the movie also. She played Jo so well! I really like her as an actress and I would like to see her doing more nice movies.

  19. Lisa says:

    She looks kinda like Tina Fey going thru Klonopin withdrawl. I loved her in Heathers, Reality Bites and Edward Scissorhands. I wish the best for her…she is talented.

    • MST says:

      Once upon a time, Gabriel Byrne was hot in a dark and brooding way, but now he looks busted, just like fellow Irishman Colin Farrell will in a few years.

      Also loved Winona in Beetlejuice.

  20. Suzie says:

    Love her! She looks incredible. Hopefully, we’ll see more of her in movies and television.

  21. Mrs.Darcy says:

    She will always be my era’s “It” girl, Heathers was my favourite movie as a teen. I do think she was her own worst enemy, didn’t pick the right roles as she got older, etc, but am glad to see her hopefully having a renaissance. It’s weird that she is the same age as Cameron Diaz, I keep thinking she’s well into her 40’s, she’s still young really (I know ancient by H’Weird standards), but there’s no reason she can’t do something more with her career if she chooses wisely. A lot of people have affection for her I’m sure, she just doesn’t seem to capitalize on it. She would look better if she put on a bit of weight I agree with other posts, but she still looks like herself to me (I don’t see evidence of the brow lift – sure that is not just a bit of botox?) Agree about Michael Shannon, so creepy/ wrong, but can’t help it!

  22. Audrey says:

    As someone said prior, she looks thin and afraid of her own shadow. I feel bad for her.

  23. Naye in VA says:

    I’ve always had a Michael Shannon thing, idk, just because he always looks like he could use a hug. I’m drawn to that type I guess. Story of my freaking life. It’s not hugs they need. It’s a psychiatrist.

    Anyway, I just saw that movie he did with Jessica Chastain, Take Shelter, and he was so freaking amazing in that movie, it took my breath away.

  24. ladybert62 says:

    I like the dress – she is tiny! I didnt know that. She has that “deer in the headlights” look in her eyes – like she is scared of something.

    Her hair is a mess and should be done different.

    Since I am not a fan of tattoos I will comment on the one on her arm – it distracts from looking at her face and the dress – perhaps that is the purpose? Tattoos are beyond my understanding.

  25. Lishka says:

    Eh, I think its called “Botoxus Maximus”! That deer in the headlights look is actually her face frozen in time, she has no other option, look at all the pics, its the same look! *SMH*

  26. hockeychick says:

    So sad..I always thought she was she looks like a formal shell of herself..remember her in reality bites? she wsa adorable.

  27. K-MAC says:

    Did she get a nose job??!!! NOOOOOO! She had the most beautiful nose 🙁

  28. Christina says:

    It’s a gorgeous dress but her body language and facial expressions are just SO awkward. If you hadn’t said it was Winona I’d never have guessed. Yes, those gorgeous big brown eyes are still there, but the spark has gone. And she looks MUCH older than 40.

  29. Ella says:

    Love her, but she looks like a deer in headlights in all these photos.

  30. bea says:

    No one is getting a ‘rexy’ vibe off of her? She looks painfully thin, not to mention painfully uncomfortable.

    • original almond says:

      I do and I don’t think it helps her look very youthful. It makes me want to feed her some hot soup and freshly baked almond bread.

  31. original almond says:

    She was so gorgeous when she was young, and she seemed so cool. I wanted to look like her so bad. So it’s doubly sad to see that she ruined her beautiful face with shoddy surgery. She has the same expression in every photo and I cannot think that it’s all because she’s nervous. The fact that she looks like she could use a few extra pounds of weight make the physical change all the more jarring.

    • Dredz says:

      I know right… A few more pounds wouldn’t hurt.

    • Ruth Dunbar says:

      The first thing I thought, and I realize this is horrible, was “where did her boobs go?” She used to have a magnificent rack. She’s very thin.

  32. Az says:

    Lainey pointed out that both Winona and Johnny Depp will be at TIFF. Winona forever, indeed. Oh how I wish that would happen!

  33. roxy750 says:

    She looks scared, fragile and very out of place, like a sheep with no fur!

  34. serena says:

    What’s with her hands.. I think she doesn’t know what to do anymore, very uncomfortable.

  35. Aria says:

    She looks really beautiful but uncomfortable. I guess she’s been away from the spotlight for so long that she became unaccustomed.

    Anyway, I’m glad she’s back.

  36. fd says:

    I don’t think she’s had plastic surgery, I think that is just botox, which looks like a “brow lift” sometimes. Whatever it is she should stop because the perma-scared look is really awful.

  37. Bones says:

    Look at that face! Some people are just born with absolutely perfect bone structure. I hope she never lets a surgeon touch that face.

    On a related note – It’s absolutely hilarious to me that this post is right next to one with Tori Spelling. Poor thing was born with the exact opposite of Winona’s beautiful face, and no surgeon has been able to improve her circumstance.

  38. Learned One says:

    I think I read somewhere a long time ago that she suffered from panic attacks. Maybe she was having a panic attack – I know I’d be super nervous!!

  39. kay says:

    If the shoplifting issue came up now, it would be over in 2 hours and people would have totally forgotten about it.

    I love her, always will. Girl, Interrupted.

  40. jak415 says:

    She looks beautiful, and also like she could be gwen stefani’s twin with brown hair!

  41. buckley says:

    It’s the Michael Shannon effect.
    Dude can be terrifying.

  42. jferber says:

    Yeah, I don’t think the shoplifting thing should have derailed her like it did. Ted Kennedy held his head high for over 40 years after abandoning that girl in shallow water after he drunk-drove off the bridge. And he was a senator for most/all that time. And that bitch Gwyneth Paltrow, formerly Winona’s best friend, saw the script of Shakespeare in Love on Winona’s coffee table, secretly read it while Winona was out and called the director to interview for the part. She stole that Oscar-winning role from Winona, who is actually a better actress than she is (Gwyneth’s range is VERY limited). So, girl, relax and take your place in the sun. You deserve it.

  43. renata says:

    I think she’s still lovely. I saw some pics of this event elsewhere, and she didn’t look so ‘deer-in-the-headlights’ in all of them. In fact, in some she looked terrific.

    It’s sad that she has her problems. Even sadder that the whole world has to know about those difficulties. I’ve always had a soft spot for her.

    There’s a woman that lives in my building that used to have a successful career as an actress — now she’s had a few kids and doesn’t get much in the way of parts any longer. She worked with WR a few times, in lead roles with her years back. I asked about Winona once. I wanted to know what she was like. My neighbor told me that everyone could pretty much tell that Winona had her difficulties, that it was obvious that something was a little off.

    I applaud her for trying to stay in the game, despite her challenges. She was mightily humiliated over compulsive behavior that for the most part, hurt her more than it hurt anyone else. It’s hard not to feel for someone like that. Some people pay a far greater price for their mistakes than others.

  44. babythastarsshinebrite says:

    She looks like she is still on drugs tho
    Her eyes are huge!

  45. F*ck you, I'm going to Guam! says:

    I wore a ‘Free Winona’ t-shirt when I was about 14.
    Winona forever!! I will never give up on her.
    She WILL come back b*tches! Like a true comeback queen! You just wait and see!

  46. Lindy says:

    I miss her. I wonder what the heck happened to her. I mean, the shoplifting and prescription drug thing seems like it should have been a setback, but not a total career-derailer. Is there underlying mental illness? Some kind of tragedy?

    I think she was/is so incredibly talented. I wish she didn’t look so deer-in-the-headlights here, and I wish she’d have a comeback.

  47. eric says:

    She has case of crazy eyes, there is a blind item that Johnny Depp shot her in the arm by accident with one of his antique guns and she’s been on the happy pills ever since, and her ex- friend complained she stole her Leather jacket and pain meds, and that she’s a total B—tch to everyone, that is why Hollywood systematically blackballed her.
    She burned too many bridges w/ people in the industry.

    • RdyfrmycloseupmrDvlle says:

      I can personally vouche for this, unfortunately. Im an actress in the theatre in NYC. She came to a gathering of theatre actors for a gala fundraisor. I was introduced to her and as I greeted her she looked away. Confused I continued greeting her and she actually turned her back on myself and others who were eager to thank her for attending. She was a compleate and total bit$h. No manners what so ever. And, this was in a period of time when she was really “a nobody” in hiding with a stone cold career. She was welcomed with open arms by this theatre company and she pretty much gave us all a big FU. Why? I have no idea. Its a shame because I really loved her in little women.
      I think Gwynth fing her and then angie jolie stealing yet another opportunity at an Oscar just permanently freaked her out. sigh. I do feel badly about her career trajectory though. Really. bad. Luck.

  48. Dredz says:

    She looks so stiff. Maybe she was nervous being in the spotlight.

  49. bgirl says:

    I would let Michael Shannon do whatever he wants to me.

  50. LeslieM says:

    It’s nice that people aren’t trashing her even though this is Celebitchy. I was cut to shreds today for saying someone was talented and looked good.

  51. Malificent says:

    I totally loved Gary Oldman in Dracula. Anybody who can be absolutely terrifying while rocking Betty Grable’s hairdo and my grandfather’s accent deserves kudos.

  52. sweetpea says:

    She has had work done to her eyes and it does not work. Also, her posture is a total affectation. She has gone to hundreds of premieres.

  53. Ginger says:

    I LOVE the day dress! Want it 🙂 My first impression is that perhaps she is not comfortable in girly clothes?? Like a tomboy in a dress possibly. She does look great for 40…probably great genes.

  54. lena horne says:

    she looks beautiful here and hope she loosens up. good wishes for her!

  55. Daphne says:

    I am rooting for her. I would love to see her have a comeback. I was a big fan of hers back in the day.

  56. Boxy Lady says:

    The nose that she got famous with was actually a nose job. If you look at really early pics of her, you can see it. The problem is a person’s nose continues to grow so years later, you have to get a follow up rhinoplasty. See: Paula Abdul.

  57. Granger says:

    I never thought she was a good actress — she was only popular because of the whole “gamine-ingenue-deer-in-the-headlights” schtick that Hollywood loves so much. I wasn’t disappointed when she disappeared for a while. That being said, she certainly seems to be in a continuous struggle with some sort of mental illness. She’s lost a lot of weight recently, and she is definitely uncomfortable at this premiere. Makes me feel kind of sorry for her — but I still think she’s a terrible actor.

  58. Ravensdaughter says:

    She looks gaunt and legitimately terrified! Poor dear, I think she has had a hard time of it in the last ten years (give or take-I don’t remember when the shoplifting incident occurred exactly)
    Getting back into the swing of the limelight can’t be an easy thing. The crime she committed pales to even one of Lindsey’s Lohan’s stunts, and I think Winona was suffering from mental illness with substance abuse tacked on at the time. I think most of us forgive her. It’s time for her to forgive herself.

  59. msjen# says:


  60. Kosmos says:

    I have to admit, she does have a “scared” look in all of the shots…gosh, if you’re going to be up there taking pics, you might as well put on your best smile, best face for the camera and not your fearful one. I like her, too bad about the negativity she has had in the past, but maybe she can turn it around somewhat. She looks nice otherwise.

  61. Allie May says:

    She probably is a little off, but how beautiful she looks!! Here is a woman that has aged wonderfully and taken care of her skin! What a difference between beautiful Winona and other hollywood actresses.

  62. insidescoop says:

    She looks like she is trying to suck it in and is not very practiced at it….

  63. ZenB!tch says:

    What’s wrong with her? Is she back on the Oxycontin? She looks too thin, her face looks jacked and her eyes look like she is about to have a panic attack.

  64. Jill says:

    I always thought she and Johnny Depp made a great couple. Talk about nostalgia.

  65. Jennifer12 says:

    I could still spout off quotes from “Heathers”- what a great film. She had a lot of talent, but she looks skinny and terrified here. Sofia Vergara is what 40 should- and does- look like. You don’t have to be scared of not being in your 20s.

    • Christina says:


      Maybe it’s because I’m a few years older than Winona myself, but I get annoyed by the ‘she looks great for 40’ comments. Firstly, she doesn’t look great. IMHO she looks gaunt and way older than 40.

      Secondly, and more importantly, she’s ONLY 40, so she’s hardly ancient. If you’re beautiful in your 20s, like Winona was, you should still be beautiful at 40, and well beyond. But she is not ageing well at all.

  66. F*ck you, I'm going to Guam! says:

    I wonder if she is still friends with Christina Ricci (?)

  67. I Choose Me says:

    Michael Shannon. Oh me, oh my, the things I would do to that man. Le sigh.

  68. Banished From Bible Camp says:

    Did Winona get Mary-Louise Parker’s face transplanted onto her head?
    Can I get one?

  69. Darth says:

    She still looks good, but imagine how much better she might look if she wasn’t a heavy smoker for the past 20+ years.
    But, all beauty talk aside, I grew up with her from her 80’s work, through her “IT Girl” reign in the 90’s, and she’s proven a few times in the 2000’s that she’s still capable of putting in a great performance, so I wish her well and hope she gets the comeback she deserves.
    This ‘Iceman’ movie looks really good, and she has ‘Frankenweenie’ to end the year with, as well as recently being signed to a mainstream action flick with James Franco & Jason Statham, so that comeback may be coming after all 🙂

  70. Zooyork says:

    Ray Liotta is so hot!

  71. Sarah Davis says:

    I think she looks soooo beautiful. I love the hair and the makeup and the whole look together. She has a vulnerability that is really endearing. Can’t see any evidence of work whatsoever – looks like shes ageing beautifully to me.