Winona Ryder looking very 90s in dark velvet: gorgeous or dated?

These are photos of Winona Ryder looking tiny and doe-eyed at the premiere of The Iceman in LA yesterday. The film stars Michael Shannon as a contract killer for the mafia who lives the facade of a devoted family man. It’s based on “The true story of Richard Kuklinski, the notorious contract killer and family man. When finally arrested in 1986, neither his wife nor daughters have any clue about his real profession.” Winona stars as Kuklinski’s wife, and it also features Ray Liotta, James Franco and Chris Evans. It’s a gritty crime thriller, and the trailer got me interested. I didn’t realize the shaggy-haired bearded guy was Chris Evans, even though I had already read he was in the film. He looks totally different! (Unfortunately he wasn’t at the premiere) The Iceman currently has a respectable 71% rating on Rotten Tomatoes, and is out in limited release on May 3.

Getting back to lovely Winona, 41, I don’t have a designer ID on her dress but I like it. I think that’s because I’m around the same age as Winona and have an appreciation for 90s styles. It’s very 90s with the deep wine-burgundy velvet and red embroidery across the bodice. (Thanks Kaiser for helping me ID the color!) I love that its somewhat conservative with the cap sleeves and tea length. On someone else, this might not have worked, but on Winona it looks perfect to me. Her messy pony and dark eyes are well done. She didn’t go with the obvious and chose a red matchy lip, which would have been overkill. Overall she looks amazing.

I grew up with Winona, so I love to see her doing well. She paid her dues and then some.

Also there we have Michael Shannon, 38, with his partner, Kate Arrington. (I thought he was older than that.) He creeps me out because I associate him with his Boardwalk Empire character. He’s a great actor, but he doesn’t do it for me.

Zach Braff was there but he wasn’t in the film. Was he ever a thing? I think briefly but that passed a while ago.

Finally Ray Liotta. He doesn’t do it for me either, but a lot of you like him.

Photo credit: Fayes Vision/

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111 Responses to “Winona Ryder looking very 90s in dark velvet: gorgeous or dated?”

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  1. Gossip Garl says:

    She looks old and scared…What wrong with her?looks like a poor scared hungry cat..

  2. pretty says:

    wow the last dude’s lower lashes are amazing…so full…

    • Itsjustblanche. says:

      I swear by Latisse. Seriously.

    • Itsjustblanche. says:

      She looks good. Great skin. Could maybe gain a little weight and smile more. But she’s lovely as ever.

      Ray Liota looks like he’s been indulging in a few too many chemical peels. Way too smooth and shiny.

      • MorticiansDoItDeader says:

        I always loved Ray’s rough skin. He looks less rugged and handsome without it. It was sort of his trade mark and he erased it 😠

  3. MooHoo says:

    synopsis sounds like one of those great 80s thrillers like jagged edge or something ray liotta would have starred in. looking forward to it. winona is forever.

    • Ms.Smurf says:

      I was surprised that Ray Liotta used to be really hot…my mom was watching that movie that he did with Whoopi Goldberg..”Corinna, Corinna”. I had to do a double take.

    • e.non says:

      years ago, hbo did a documentary on the iceman; with extended prison interviews. he is/was one nasty, remorseless man. he was so matter of fact while recounting the murders he’d committed — a couple of which were so gruesome i recall exactly what he’d done.

      • Sugar says:

        I watched that & was mesmerized by his matter of fact way he told his story. Creepy scary evil dude just doing his job taking care of his family.
        As far as Winona i grew up with her movies so I’m 4ever Winona.

      • Karma says:

        I remember that doc and kept missing the beginning but it was hard to channel surf past The Iceman and wait to see it from the beginning.

        There aren’t a lot of movies or docs I will stop and watch in progress, repeatedly, but that was one of them.

        Didn’t realize they had made a film of him.

  4. Nancy says:

    She looks great!

    • Becky1 says:

      I think so, too (although she’d look better if she smiled)! I’m surprised regarding some of the comments about her looking old. I don’t think she looks old at all. She’s in her early 40’s and she looks great.

      I like the dress but it really is very 90’s (in a good way). One of my friends had something very similar back in college (I graduated in 1994). I also had a couple of velvet dresses back then.

    • Kare Bear says:

      Just wanted to chime in with my agreement. I think she looks really good. I don’t really get the “she looks so old” stuff. I mean, yes she has aged but, IMO, well.

    • ZinJoJo says:

      I love her and think she looks great. For me, she totally epitomizes the 90’s, but I loved the 90s! Peace, balanced budgets and comfortable shoes.

    • LV says:

      I agree that she looks great and if you compare her to her contemporary Gwyneth
      Paltrow it’s pretty interesting to note that Gwyneth who is obsessed with her body and her clothes and her diet, really doesn’t even look as half as fresh or beautiful as Winona who is a bit older. Go Winona!

  5. ladybert62 says:

    Does she ever NOT Have that deer in the headlights look?

    • V4Real says:

      I was just thinking the same thing while scrolling through the pictures.

      Looking forward to The IceMan; Shannon is a great actor.

    • Miffy says:

      Speaking from experience that deer-in-the-headlights look is really hard to avoid when your eyes are naturally that round. If you’re not smiling in photos you look terrified, ALL. THE. TIME. It’s just the face/eye shape.

  6. Beth says:

    She has crazy eyes.

  7. Kelly says:

    She looks good, but scared. Love the dress. She used to wear vintage a bit.

  8. BooBooLaRue says:

    When they make the Nancy Reagan bio pic, I hope they ask Winona to play the part. Scary.

  9. Agnes says:

    She looks good? But I hate, hate, hate velvet, so I can’t be objective here.

    Love Zach Braff and Ray Liotta! Awesome actors.

  10. dcypher1 says:

    I grew up in the 90s too so WINONA FOREVER. She looks pretty here love the dress too.

    • JenD says:

      I grew up watching her, too, so I love her. I think she looks great here, and I like the dress on her.

  11. gabyrana says:

    she looks pretty, for a moment I thought she looked like Tina Fey.

  12. Joanna says:

    Winona is so pretty! beautiful complexion. if she didn’t have her hair up in kind of a matronly hairdo, she wouldn’t look her age.

    • tripmom says:

      I agree. The poofy hairdo is what makes this look dated. A sleek modern ponytail would have made the dress look fresher.

      • J.Mo says:

        She would look gorgeous with professional hair and make-up. She doesn’t just resemble Tina Fey, more like Tina as Palin.

  13. Dawn says:

    I think she looks great, and she looks younger and fresher than say people who are 10 years her junior. Ray Liotta is in his 50’s and looks just fine for his age. Ease up people…young and pretty doesn’t last forever but TALENT does. And this is a talented group.

    • V4Real says:

      You’re right they are all talented people.

      I just wanted to say that Halle Berry, Diane Lange, Cindy Crawford, Angela Bassett, Stacey Dash, Courtney Cox, Cate Blanchett and Ellen Pompeo just to name a few are all older than Ryder and they are still quite pretty. Sure some may have had some help from Botox but looks like Winona may have done so as well. Some women just age better than others.

      • Dawn says:

        Yes your are right. I think I am just trying to make up for when I was young and didn’t understand the beauty of some the aging stars of the time like Liz Taylor and Maureen O’Hara and Doris Day just to name a few. I watch some of their old stuff now and I am blown away by how pretty there were at any age. And how talented they are. So now I stick up for my age group a little too much maybe. I think as you age you understand how brains and personality trumps beauty in the long run!

  14. ctkat1 says:

    Michael Shannon read that sorority girl email for ‘Funny or Die’ and it’s pretty amazing.

  15. mel says:

    She looks great!

  16. Happymom says:

    Whoa-that Ray Liotta close up made me jump back.

  17. eileen says:

    CB-I feel the same way about Shannon! He’s TOO good of an actor on Boardwalk Empire so now all I see is him flogging himself! lol

  18. Quinn Parker says:

    She always seems like she’s two seconds from going full-blown postal.

  19. Lemony says:

    She looks really good.
    Compare her photo to that one in the featured links of JenniferLove Hewitt exploding out of her dress….Winona looks elegant.

  20. marie says:

    I love Winona but that hairstyle makes her look like a bobble head..

  21. Eve says:

    I apologize in advance for what I’m about to say: Ray Liotta looks like David Hasselhoff here.

  22. Suze says:

    I honestly thought this was Tina Fey.

  23. DreamyK says:

    Michael Shannon’s reading of the Delta Gamma sorority letter was epic!

  24. fabgrrl says:

    She looks pretty good, better than the last time she was out and about, I think.

  25. serena says:

    Oh come on Zach Braff is amazing.

  26. MorticiansDoItDeader says:

    I wanted to be winona when I was a kid. Loved her in Heathers and Beetlejuice. Her pasty white skin and black hair were striking. I don’t know if it was her look or the roles she chose, but she always radiated this strange and unique beauty. Now I just look at her and feel sad. She always looks so lost and you never hear about her dating or having meaningful relationships.poor Winona 😔

  27. Kristin says:

    I gotta disagree with the negative comments here. I think she looks fabulous! She has amazing bone structure and she’s always been petite, so I guess I could see how some people think she looks scrawny, but I think she looks great.

    And it does bother me that such a legitimately talented actress saw her career bottom out after her arrest. Yes, she did wrong and I’m not excusing her behavior, but far less talented idiots in Hollywood do worse shit all the time and get forgiven for it. Christ, look at Lindsay Lohen. Her rap sheet is longer than “War and Peace” and she’s still around. And she hasn’t got even 1/10 of Winona’s talent. I just like Winona and I’ve loved her since Heathers. I’d love to see her get more work.

    And on the subject of the “Iceman” premiere, I’ve actually read the book and for any of you who haven’t, let me say that it is worth the read. Richard Kuklinski was one seriously horrifying dude who is estimated to have murdered upwards of 200 people, and in ways that will give you nightmares. Dahmer and Bundy look like boy scouts next to him. He’s also been unofficially confirmed to have been one of the hitters that took out Jimmy Hoffa. The book is called “The Iceman: Confessions of a Mafia Contract Killer”. The author is Philip Carlo. Seriously all, it’s a hell of read!

    • akua says:

      Didn’t she ‘bottom out’ though, basically because she was crazy, high, and a bitch? Just rumors of course, I guess you never know! I always did like her though

      • Miffy says:

        Well the current high and crazy bitch spent last summer (?! or whenever) portraying Elizabeth freakin’ Taylor. I think Ryder deserves some slack.

  28. vv says:

    I have a friend who says when she was 16, she and a friend were approached by some kind of ‘assistant’ who asked if they wanted to come on the set of a movie being filmed in the area, and meet a movie star (in his trailer).

    The star was Ray Liottta.

    Needless to say the girls declined but the story is still unsettling to me. I know he is not the only one who has people doing this on his behalf but 16? Gross.

  29. pam says:

    yes, she looks weird. she looks like “oh, i’m not used to all these cameras” really? Wynona, youre famous, youve been famous for what 20 years? stop looking like you hate the fame, if u hate it, stop making pictures.

    Michael Shannon is weird looking too. i can’t believe he is only 38. but i love him, he always plays such great characters.

    • Jm says:

      Sadly, she is not looking scared or hating the fame; she had bad plastic surgery and now her eyes always look like that. A cautionary tale . . .

      • EmmaStoneWannabe says:

        oh no! Really? So youre saying her eyes are going to be stuck like this? Ughh! I just assumed it was from some bad Botox-ing and they would eventually settle.

    • Cleveland Girl says:

      Michaels girlfriend looks like she is completely coked out

  30. andy says:

    Winona looks pretty.

    She was absolutely stunning in Dracula. One of the most beautiful women ever in that film.

  31. tracking says:

    She is gorgeous but looks very frail.

  32. Mary Ruth says:

    She looks lovely. Go Winona!

  33. Kristen says:

    Oh jeez. I thought that was Tina Fey at first! In my defense, I haven’t had any coffee yet.

  34. Ravensdaughter says:

    Winona can wear whatever she wants-just glad to see her out and about after a long hiatus…

  35. Nanz says:

    God I love Winona, but why is she dressed and styled like my dead grandmother?

  36. Aria says:

    Beautiful as ever! I agree she looks like Tina Fey in some pics but both are beautiful ladies.

  37. bns says:

    When I was growing up I wanted to be her. In her prime she was seriously the most beautiful woman in the world. Still gorgeous.

  38. Hakura says:

    I’m in the complete minority here… Not at all to discount positive things said about her, but I immediately thought “She looks -very- underweight, & like someone above said, frail. Like a little old lady.

  39. Janet says:

    Love the dress. It’s refreshing to see a woman her age dressing her age.

  40. Stubbylove says:

    Huge luv for Winona. Gotta give it to Ray Liotta – the guy always looks like he’s constipated or holding in a huge fart.

  41. mar says:

    she look totally disturbed, as always.
    Did she have a bad eye job?

  42. Ginger says:

    I was never a huge fan of hers as an actress but she is from the same neck of the woods that I am and I’ve never heard a bad thing about her. She’s a lovely person and is aging gracefully which is refreshing to see.

  43. nuzzybear says:

    From the home page, I just saw Winona next to KStew – they could totally play mother and daughter… in a story where the mother steals her daughter’s sensitive English boyfriend because she dresses so much better.

  44. Baskingshark says:

    Hey Ray Liotta, Nicole Kidman called – she wants her title as the most plastic surgeried person in Hollywood back.

  45. Lisa says:

    WINO FOREVER. I want to look like her and be her best friend at the same time.

  46. lucy says:

    The emerald jewelry looks spectacular on Winona. Good to see her out again.

    Michael Shannon has been my favorite actor for the past 9 years. Props to him!

  47. KellyinSeattle says:

    I think she has panic attacks…that’s not easy and probably adds to her frailty.

  48. Just Me says:


    Wino forever, bitches!

  49. Hooper says:

    She looks crazy!

  50. WTF says:

    Ray Liotta – too much.

    Too much plastic surgery, too much mascara, too much hairspray.

  51. Granger says:

    I remember so many magazine interviews with Winona where the writer would describe her as “frail,” “delicate,” “tiny” (which seemed to be a euphemism for “helpless”). After a while, it got really annoying. Now, I just want to shake her and say, You’re 41, for pete’s sake. Throw your shoulders back, smile like you mean it, and stop acting like a scared little girl.

    She’s still beautiful, though.

    • Stubbylove says:

      spot on.

    • Karma says:

      The only thing about throwing your shoulders back when you are busty is that it never comes off well.

      Look how many busty women slouch to hide their girls. It’s a lifetime of side-eyes and comments from men and women that inspire such a subdued posture.

      Anyway, I think she looks great.

  52. EscapedConvent says:

    Winona has always looked exquisite, but a bit frail, I think. More frail now. But that may be because we haven’t seen her in a while.

    I still think she’s lovely, & the deep wine is a beautiful color on her. Also, we’re so used to seeing boobs worn on the outside of clothes, & mini-skirts you can’t sit down in, that when someone wears a dress that covers their flesh, we think it’s conservative!

  53. Chickie Baby says:

    Winona’s dress is very lovely…just not in April! A little dark for spring, is all.

  54. Lulu.T.O. says:

    She would have looked much better without the Sarah Palin hair style.

  55. emma says:

    she looks so great! i wish my eyes could look like that.

  56. lisa says:

    she looks like tina fey if tina had the crazy eye

  57. Agnetha says:

    I think she is a great actress and am just happy she is making more movies these days! Edward Scissorhands is one of my favorites along with Mermaids, I will always have s soft spot for her.

  58. Kristine says:

    She always looks frail and scared. That’s just her thing. Love her dress.

  59. Dana M says:

    She looks great. Hopefully I will look this good when I’m 41 (sans the eye surgery of course).

    We ALL are going to be 41 someday!

    • Adrien says:

      She’s ONLY 41. Countless stars older than her looks refreshing on the red carpet. She looks like she’s channeling Mrs. Nancy Reagan with that look. She looks like she’s a grieving widow. Shame coz she’s really, really beautiful.

  60. Jennifer12 says:

    Her hair looks weird and she looks terrified. It’s like she’s trying to get her quirkiness back and she can’t quite hit the right notes anymore.

  61. lurker says:

    Winona looks very pretty, she can afford 2 or 3 pounds more to look healthier. I also dislike her hair updo. I want her to cut her hair a short bob, she always looks great in short bob. (I think short hair also suits smaller women better – I wish I could tell Kristen Chenoweth that)

  62. whateveryouwantittobe says:

    Man, Ray Liotta plays the rapist/bad guy so well I am creeped the eff out by him at all times.

    I want to see a day in the life of Winona, and I never ever want to meet her.