Maggie Gyllenhaal Style Double Shot

Posted on April 08, 2014

If they ever do a Ruby Keeler biopic (which doesn’t seem likely, since we’re pretty sure 90% of the people who just read that name said “Who?”) she needs to be first in line. She’s the spitting image of her. And because she has a face straight outta 1930, her best style attempts occur when she dresses to that effect. Not that we think she needs to dress in retro styles; just in styles that evoke Depression-era Hollywood fashion (because there was no “fashion” going on anywhere during the Depression except in Hollywood). These two looks are perfect examples of doing ’30s style while still looking modern.



Maggie Gyllenhaal attends the photocall of “Honourable Woman” photocall at MIPTV 2014 in Cannes, France in Chloé.

Chloé Fall 2014 Collection

We love this look. We think, on a different gal, we’d find that dress annoyingly over-ruffled, but we didn’t even notice how ruffled it is until we really started assessing it. At first glance, it looks breezy, feminine and romantic. At second, third and fourth glances too. And we love the chic little flat sandals paired with it. Perfect both for the dress and the setting.

This next one isn’t exactly 1930s style, but it does have a retro feel to it, borrowing both from Renaissance clothing and from the embellished and heavy styles of the Edwardian period, with just a tiny bit 0f 1920s. It’s basically all-purpose retro and again; it just plain works for her:

Maggie Gyllenhaal attends the MIPTV Opening Ceremony in Cannes, France in Valentino. on April 7, 2014 in Valentino.

Valentino Fall 2014 Collection

Granted, the waist could use a little taking in because this kind of hangs on her, but the style and the color story are perfect for her. Love it when she puts the effort in. She’s unique in her style  – and that’s a very hard thing to find among the celebrity set.





Please review our Community Guidelines before posting a comment. Thank you!

  • RussellH88

    I really love the first dress. It looks just so fresh and she makes it appear effortless. The second dress is iffy, it’s like “meh” Florence dress.

  • HomeOfficeGirl

    LOVE the 2nd dress…that is perfection for her for sure. The first dress is ok… but I really hate the flat sandals here. I think because it’s a lot of dress, with long sleeves…. so such a bare and casual shoe looks out of place. BOTH looks are refreshingly free of Maggie dumpiness…

    • tallgirl1204

      She’s got a big bandage on her left foot, so maybe bare and casual was the only option she had that day… I’m not a huge fan of those sandals either, but then, I’m usually the one in flip-flops so I have no stones to throw…

      • HomeOfficeGirl

        I’m flip flops all the way myself. Just got back from Spring Break and I have cramp in my arch from one day of wearing normal shoes. If she has to go easy because of a foot injury, I’m wondering if a cute light espadrille wedge? Something with a teensy bit more substance??

    • Sarah

      OMG I’d take those sandals ANY DAY compared to the Napoleon Dynamite boots on the model. Yikes.

      • HomeOfficeGirl


      • kimmeister

        But don’t you want to dance to a Jamiroquai song right about now?

        • Imasewsure

          And show us your Sweet Moves!

      • Beth Swartz

        +1 just for the mention of Napoleon Dynamite.

    • kimmeister

      I don’t like the sandals because they’re too . . . Birkenstock-y to go with a chiffony dress. But I’ll give her a pass because of the possible medical limitations she had that day.

    • sojourneryouth

      I also adore the second dress on her–really fits her style. I would like the first one as well, but I need about 50% less frippery on the front. She’s a thin woman, and I think that much ruffle action is distracting. The clean lines of the second dress are more flattering.

    • demidaemon

      Agree with you on the shoes. I just don’t like them in general. I would have preferred a cute flat or more substantial sandal, if she had to go that route.

  • tallgirl1204

    I think she could potentially also work Myrna Loy– although I don’t know if she has the zany cheerfulness in her that M.L. used to work up in those Thin Man movies.

    • Beardslee

      I could see her with the Myrna twinkle in her eye. I love Myrna Loy. So cheerful, so free of neurosis, at least on film.

    • 3boysful

      I have an Asta dog!

    • fursa_saida

      She totally does! Watch Hysteria. Even if you disagree, you will not regret it. It’s a period rom com about the invention of the vibrator. Hugh Dancy and Rupert Everett, too. She’s a cheerfully vocal 19th century feminist, it’s just all amazing.

  • MW

    I would go as far as call the second look her personal best. She looks great with blond hair.

    • kimmeister

      The hair color has really helped the issue she had before with her brows being too light/sparse for the dark hair.

      • ballerinawithagun

        Yes! I love this hair color on her.

    • Daisy Walker

      I would never have guessed that she’d be a good blond, but it totally works!

      • Denise Alden

        I know! I usually don’t like blond hair on so many people, but man, she looks terrific!

    • jtabz

      Yes! Was coming on to say exactly this, MW 🙂

  • Shawn EH

    The other question is … can she dance? That Valentino collection is so perfect for the quirkily originals on these pages: Maggie, Rashida, Florence Welch.

  • Frank_821

    Yes she could do Ruby Keeler. Wonder if she can tap dance?

    overall nice looks

  • StillGary

    what a great hairstyle she has now — would love to see how she looks in a little in a little cap — I don’t always like all of her films, some are just a little too gritty for me — but she is a very talented actress and I like how she looks — an attractive woman who looks real.

  • rkdgal

    I think these are both personal bests (not that it was a high bar to get over…). Well done, Maggie!

  • hughman

    Plan B : play lead in movie of the Barbara Corcoran story.

  • decormaven

    Wish a bracelet or earring had been chosen to pick up the blue in look #2. Her new hairstyle/color really updates her look and brings out those gorgeous eyes.

  • leahpapa

    I’m shocked by how much I’m liking the blonde on her!

    • eowyn_of_rohan

      Same! I never even entertained the idea of blonde!Maggie and I was prepared to detest it when I heard she’d ditched the brunette. But this is really working for her.

    • Danielle

      I had the exact same thought. Her eyes really pop!

  • @Biting Panda

    Y’all know I love and support my Maggie, so I’ll just say, it’s nice to see her here.

  • Glam Dixie

    Just going by what y’all post of her here on your site, these looks both look like personal bests. Love them both.

  • marlie

    She knocked it out of the park on both occasions here. Maggie doesn’t have to give up her boho/granny-chic aesthetic, but it serves her really well to apply a slightly more modern and upscale twist to it. Attagirl!

    • Constant Reader

      Agreed. And less overwhelmingly baggy.

  • zenobar

    Wow, Maggie really could do Ruby Keeler justice! I read “I’ll Cry Tomorrow” by Lillian Roth when I was a kid (book nerd much?) and she talked about competing with Ruby Keeler for roles – they were both born in 1910 and attended a performing arts school together, I believe.

    (OK, not just a book nerd. More of an all-purpose nerd.)

  • majorbedhead

    I love that first dress. It’s lovely on her. And I’m really liking her with blonde hair. I’m not completely sold on the second look, but it’s 110% better than most of her red carpet looks.

  • Kate Andrews

    I love the hair!

  • I’m surprised by how awesomely that Valentino dress translates to the red carpet. When I saw that collection I thought most of it would never be seen on the red carpet at all. And yet, here this dress is, and on the right person honestly that dress is breath-taking. All the little details are just incredible and I suspect are even more incredible closer up.

    I think Maggie could easily rock virtually every dress in this collection. She does have that gothic goddess vibe going on. 🙂

  • Tanya Wade

    I know who Ruby Keeler is, and I concur! I, too, am liking the blonde hair. She looks really good in these two photos, better than she has in, oh, forever. I would normally think the white dress was a little too flowers on a parade float, but it seems to go with Cannes.

    She is one of the mister’s big time screen crushes, so I always try and give her a break.

  • ccinnc

    I would never have thought she could go blonde, but I like it on her, very much.

  • KinoEye

    That Valentino is the best I’ve seen her look in a while. Perfect for her, and surprised to be loving the hair.

  • MilaXX

    I like both these looks on her, and to my surprise I also like the hair. Didn’t someone else try to wear that second dress unsuccessfully a while back?

  • jonnyf8

    The first dress is her personal best. The second dress is something Florence Welch wears around the house when she’s pretty sure no one’s gong to drop by.

  • Jessica Freeman

    I am not a fan of the first look at at all. The sandals seem a bit too casual for the dress. The second look redeems everything. She looks amazing. Not fully in love with the blond hair but I really love the cut.

    • Vtg Fashion Library

      If you look, her left foot is wrapped, so perhaps the casual sandals are due to a foot injury. I loved the first look in the thumbnail, but it’s scrolldown fug for me. The second one is pretty on first glance, but the more I look at it, the more I see Caroline Ingalls meets Gunne Sax. Love the hair though.

      • Jessica Freeman

        I noticed the foot wrap, but there are plenty of flat sandal options that are a bit more dressy. I applaud any flats lady stars wear since that is my go to shoe these days.

  • Kathy

    I guess it’s just me, but the first dress looks like a toilet paper extravaganza. The Valentino is gorgeous.

  • In_Stitches

    The new hair color makes her eyes glow. She’s never looked so luminous.

    I’m not sure if the new hair has invigorated her fashion sense or if she just looks better on the whole because of the dye job. Either way, it’s working.

  • Lori

    I have to disagree about the first dress. She is not wearing it, it’s wearing her. She doesn’t have the fashion attitude to even come close to pulling off a dress with that much going on. I agree that the idea was in the right direction for her, but the actual execution is not working. There is way too much hanging off that neckline. I’d probably be inclined to cut the look more slack if it was in a color, but as is it’s fancy toilet paper.

  • Kayceed

    I like the first dress, although the ruffles are looking a bit unruly around the neck and I REALLY wish they would have kept the handkerchief hem – the straight hem is a bit odd. The second is just lovely. I would have put a fancy metallic belt on her as well.

  • Judy_J

    I’m one of the 10% who know who Ruby Keeler was, and yes, Maggie is her twin. I really like Maggie with the blonde hair. It suits her, and really makes her blue eyes pop.

  • jilly_d

    That Chloe is so perfect for her. No one else could make it look that good.

  • I’m shocked how much I like her blonde – and these are exactly the sorts of unusual styles that play to her strengths. WELL DONE.

  • Evan

    Love the first dress. I think the second dress would look better on somebody with a darker skin tone, like Zoe Saldana.

  • Vanessa Reyes

    Loving the hair…Maybe a stronger lip for the second look.

  • Judy_S

    I dislike the Valentino quite a bit. I think it looks quite dignified, yes, and comfortable too, and just the thing for the mother of the bride at a Renaissance-themed wedding.

    I love Maggie in the white ruffles, though. It’s great to see her in a “double shot” too–I was kind of dreading opening it up on two awkward looks. But no! She is standing up straight and looks lovely even in a dress I don’t like.

  • Christin Pardy-Nosenchuk

    I love love love her as a blonde.

  • Beardslee

    Ruby Keeler! You are so right! It’s so obvious – once someone has pointed it out. Thanks.
    As a rule I deplore the default to blonde by actresses but I agree with the BKs who think she looks just right.

  • RichStrathmann

    When did Maggie Gyllenhaal turn into Sharon Stone?

  • Imasewsure

    Love both dresses but kind of hate the sandals with the first one. A few inches longer on the length and they would have looked perfect. Love that dress on her though. The combo of the boyish cut and the super-femmy dress is just right.

  • Fuchsiaforever

    Perfect dresses both. Hate the blonde, she needs to go back darker to a darker shade. The blonde makes her look ANCIENT, like she was BORN in the 30s.

  • RuthGo

    I love both of these dresses but I really question those sandals. I think flat sandals in white and less Birkenstock-esque would be better. They just don’t have anything to do with the dress.

  • alyce1213

    I love the way she looks in both of these, and blonde hair is really great on her — it unmousies her. I do wishes she’d chosen a different flat sandal for the first dress. Given her foot injury and the sur la plage location, sandals are in order, but not those — something with a little prettiness.

  • bessann28

    I love the first dress, but I think the sandals do not go with it at all. They look like something you’d wear with khaki shorts.

  • MightyMarshal

    Do you guys ever hear from Laura Bennett? Way back when you guys first started this blog adventure I found you from Googling Laura Bennett and have been following you ever since (occasionally/rarely commenting) and I remember you guys being pretty close with her and seeing the occasional post with an update about how she was doing but I haven’t seen anything in a while, so I thought I’d ask.

  • crash1212

    Not crazy about the first look and wonder if she chose the sandals because she had a big old honkin’ bandage on her left foot! As for the second look – LOVE. IT. Maybe she should just wear that dress to everything all the time. Not crazy about the hair – she’s not a blonde and hope that’s for a role – although, her hair is always ghastly to my eye.

  • Joanna

    This is the best she has ever looked, IMO. Blonde suits her.

  • Janet B

    Love the second look, her eyes and face are so alive.
    I love seeing any stylish dresses that have long sleeves.

  • Clash D

    I’m so happy for her. She’s found her fashion groove at last.

  • Call me Bee

    Ruby Keeler yes! I love her new white hair–it really suits her and plays up the 30s look of her cherub-face. The dresses? The first one is really beautiful, but I did a record scratch at the shoes. I woulda preferred something more ladylike and less beach-like.
    The second dress is not attractive. On Miss Maggie or anyone.

  • Kelly

    I love the first ruffly dress on her. The second one I don’t like at all — way too matronly and Pat Nixon-y.

    *wanders off humming ’42nd St.*

  • Cheryl Smith

    Where have I been?? I love the short, blond haircut!! She makes a great blond IMHO. I love her in both dresses.

  • bitchybitchybitchy

    It’s interesting-in the first photo I don’t like the ruffles on Maggie,but in that second photo there’s some sense of movement and the dress works.
    As for the second look, if it were fitted closer in the waist it would be more flattering. Is the blond hair for a new role?

  • Wow. I hated her hair when she first cut it – now I freaking love it. Amazing how changing up the hair color makes that style work for her.

    Love the dresses – she really can pull off difficult clothes.

  • MarissaLG

    The shoes in the first looks aren’t good, but it looks like her foot might be injured so I’ll give her a pass. LOVE the second look- I think it’s so chic.

  • Wink

    The hair really works for her. She’s almost as pretty as her brother, Jake.

    • Mousentrude

      Like the style but wish she’d go back to brunette, the blonde gets lost next to these dresses.

  • paginatrix

    I always see Claudette Colbert in her. But YES. The retro-but-modern thing is hers. The blond is pretty on her, too.

  • Sabin

    I’d have loved to see some kind of kitten heels sandally shoe with the first look, but otherwise it’s lovely. Those sandals are sort of jarring for me.

  • Gatto Nero

    I love her in both these looks and really appreciate her singular and very personal style choices. She is a breath of fresh air, in that she is unapologetically herself, in the way that Helena Bonham Carter shines for me, too, even if I don’t love every single thing they wear.

  • berkeleygirl

    I say this about few women, especially celebrities, but she looks incredible as a platinum blonde.

  • Esz

    The blonde is looking amazing on her! Really brings out her features in a nice way.

  • Footlight Parade is still a must see movie for me: Ruby Keeler, Joan Blondell, James Cagney.
    * hums By a Waterfall*

    • Columbinia

      “Honeymoon Hotel,” “Shanghai Lil.”

  • B_C_J

    Love her as a blond!! Love her unique style. The ruffled dress looks better from the side. The Valentino is exquisite on her.

  • nannypoo

    Two great outfits in a row for her. Unbelievable. And she looks great. I love her hair.

  • LaSylphide

    What a pleasure to say something (actually, everything) good about the way she looks. Terrific dresses, and that blonde hair is fantastic: i really hope she keeps it that way.

  • nicewilliams

    She’s also taken to wearing a bra again, which helps loads.

  • Anne

    I love her lipstick color in the second picture. It’s perfect!

    • MaggieMae

      Me too. I want to know the brand/color!

  • Judih1

    Both looks are a personal best for her! Goes to show a leopard can changes its stripes. The first one I LOVE LOVE LOVE, but would have chosen a different color sandal. Not really liking a flat sandal at all with the dress, but given her foot injury I will give her a pass. Still a bronze, brown, leopard print or cream color shoe would have been my prefernce over the red.

    Love the second look on her and love her as a blonde

  • CPK1

    Love the Valentino. I want a dress from that collection sooo badly

  • mjmiller77

    first a bunch of bibs, then a granny gown. yuck on both. too bad, becuz she’s gorgeous

  • Columbinia

    Ha! I first saw Ruby Keeler movies at art house and repertory film theaters when I was in high school. I know exactly who she is. It may be film trivia, but she was the cute star of a lot Busby Berkeley movies. Busby who? Oh, go google it.

  • Qitkat

    This is the first I’ve seen of her in her new blonde do. A great look, and she has stepped up her fashion. I would love to own either of these looks. Pretty darn far from the thrift shop queen. I’m impressed.

  • John11581

    Wow, it’s a good thing I was sitting down when I looked at this! I never thought I’d ever see her looking as great as she does in that first dress. Perfect for her, and the perfect setting for it. Not an easy look to pull off, and so far from what’s come to be her default, crazy spinster look. I’m not as sold on the second look but, had it not been paired with the awesomeness of the first, I’d be giving her some high praise for it too.

  • formerlyAnon

    I’m not in love with the first dress (it’s fine, but “much ado about nothing” comes to mind when I look at all that ruffliness), but I love the second on her.

  • Sam Smith

    Really dig the first look.

  • FridaStaire

    Love first. Second – sister wife.