Girl, That’s Not Your Look: Debra Messing at the Tonys

Posted on June 10, 2013

Sweet Jesus on a breadstick, girl. What is wrong with you?


Debra Messing attends the 2013 Tony Awards at Radio City Music Hall in New York City in an off-the-shoulder Matthew Christopher couture dress with a belt accessorized with Fred Leighton jewelry and Brian Atwood shoes.

Matthew Christopher Spring 2013 Bridal Collection

Have you no mirrors? No gays? A stylist that isn’t vision-impaired? Is that man of yours incapable of giving an honest answer to the age-old question “How do I look?” Fine. We will step up and fill all four of those roles for you. Brace yourself.

Honey, that dress is actually quite cute, but – and we don’t like being the ones who have to say this to you, but we take comfort in the fact that we’re not in any physical danger at the moment – it’s a dress designed for a smaller, younger woman. That’s the truth of it, girl. It’s not fair, but there it is. There are plenty of sleeveless little black dresses with cinched waists out there for you, but this isn’t one of them, doll.

Also: the big drag queen knot top is NOT helping.



[Photo Credit: Marco Sagliocco/PR Photos, Getty,]

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

  • eowyn_of_rohan

    Debra, why? You used to have taste!

    • carpediva

      Um, when was this?

      • eowyn_of_rohan

        About 10-15 years ago, when Will & Grace was flying high. She did have a few good looks. Not what I considered any kind of style icon, but she always seemed well put together. It faded fast, I guess.

        • carpediva

          I THINK I remember that. Maybe she had access to the show’s stylists then or something.

        • Yuju Ti

          I thought her stylist was Rachel Zoe….No?

      • Rand Ortega


  • Virginia McMurdo

    Whew… she looks so rough.

    • stchoo

      A few seasons on Smash will do that to you…

      • drdarke

        @stchoo:disqus – did the SMASH cast get together and decide to show up in the worst outfits imaginable? Between Debra Messing and Megan Hilty, I’m can’t help but feel they’ve decided to pull off a piece of Performance Art on the Tony crowd….

  • PeaceBang

    I did the gay gasp when I saw her. But the BAD gay gasp, not the good one.

    • decormaven

      Shock, utter shock. I’m going to replay “The Wedding Date” just to get this out of my mind.

    • mhleta

      The bad gay gasp is more of an inhaled shriek. I did it too.

    • drdarke

      Me, too, @PeaceBang:disqus – and I’m straight.

      Though you’ve all been a great help on that score….

  • Maryanne525

    MERCY. She looks like a little girl on her way to Christmas Eve church service with a purse she got from Claire’s Accessories Classy Collection.

  • Rocío Vázquez

    Also she should change her make up, I swear she has worn that same eyeshadow for decades now!

    • Sobaika

      Yes, and she should wear less makeup. She’s a very beautiful woman, she doesn’t need to be shellacked like that. I’d be afraid of getting rubbed off on if I were her date.

  • meowing

    As a BK with larger than average upper arms (paws?), even I know that teeny weeny cap sleeves are my enemy. That’s not even addressing the lower half volume where no volume is needed. And the hair, oh, the hair. Such a gorgeous woman. Such a sad look.

    • Sobaika

      Death to cap sleeves!

      • Catherine Katz

        Amen! I will join you in the funeral parade (cause it must be sassy!) for all cap sleeves! Ugh!

      • Mary229

        Yeah cap sleeves don’t do average size arms any favors.

    • ToothCake

      Agreed on cap sleeves! In Mindy Kaling’s book, one of my fave parts is her view on cap sleeves…”Cap sleeves should be worn exclusively by toddler flower girls at a wedding.” 🙂

  • OrigamiRose

    Is it me or do her ankles seem *really* swollen? Maybe it’s the angles/lighting, but both look like baseballs fighting to escape her legs.

    And chipped toenail polish at the Tonys? Debra, you’re a mess.

    • GorgeousThings

      I don’t think the nails are chipped – it looks like a lighting/reflection issue.

      But boy, at least her left ankle looks really swollen. I’m hoping that’s just an artifact of the camera angle. So are she and creepy guy from “Smash” really an item? I’m so out of the celebrity loop these days I have no idea who’s with whom.

      • Donna Tabor

        She doesn’t look especially healthy right now, frankly. Or maybe she looks too healthy, can’t decide.

      • OrigamiRose

        Thanks! I looked at her feet far longer than I probably should have but I found myself mesmerized by the size of those ankles.

        It does sound like they are a thing. Too bad I never watched the show or I’d know who he was *grins*

      • Felicia Zuniga

        They are. Which has got to be awkward for the first wife he left for a virtual child and the virtual child he left for Messing.

        • formerlyAnon

          The first wife is probably *well* over him. Especially if she had a decent lawyer. The virtual child should not have been surprised. If someone leaves somebody for you, it’s beating the odds if they are under 60 (under 70 if they’re wealthy) and don’t leave you for somebody.

  • Daniel

    She looks like a poorly-dressed vampire.

  • Annarosa

    the disturbing thing is… is… well, everything. Too bad, because she’s gorgeous, but here she’s almost unrecognizable.
    Debra Messing is messing around with fashion, let’s say.

  • majorbedhead

    Oh dear. Oh, no, that is not a good look at all. And what is up with the streaks of bronze blush? It makes her face look dirty.

  • Good jewellery but nothing else about this is working for me.

  • I haven’t seen a lot of pictures from the Tonys yet, but I feel like off-the-shoulder black capsleeves were overrepresented.

  • kipper

    In her favor – and really it’s just the rosy glow from last nights wonderful show lingering – it did look nice while she was sitting in her seat – and she was cut too pretty often, but on the rc it is just horrible….

  • There is a thick layer of delusion on this one.

  • Julie Chase

    She’s a lovely lady, but this does nothing for her figure. And oh that hair.

  • sarahmichelef

    I think it’s time to keep score of the people who most often show up as negative examples… the “you might also like…” section is telling me that this is AT LEAST the third time in a year that Debra has done so…

  • THAT is a party dress for a 16 year old.

  • clatie

    Dear Debra:

    I am a woman about your age and I recently realized a few things. I share them with you as a friend. It brings me no pleasure to say these things.

    We can’t wear the same clothes we used to wear. Our bodies have changed, our faces have changed. They just have – although WE STILL LOOK GREAT. We just don’t look the same.

    Look at working with slinky shapes. DON’T try and do any literal retro look because it will look like you just took old stuff out of your closet. DON’T get inventive with your hair. You will look demented. DON’T wear ANYTHING from a bridal collection even if they remake it in another color for you. That stuff is for younger women and will make you look sad.

    It’s a tricky time – trust me, I know.

  • Latin Buddy

    Is Rachel Zoe still her stylist? If so, Zoe has had a really bad award season. Anne Hathaway’s Oscar dress disaster, J. Lawrence trips on her dress, and overall the quality has been off.

  • Daisy Walker

    Mutton dressed as lamb.

  • Edwina3

    She hasn’t learned to dress her body post baby weight and marriage break-up. She does look happy but the rest of us are sad. A black, figure hugging sheath paired with a soft chignon hair style would suit her well.

    • AshleyDeHaye

      That’s what I think. I am not body-snarking when I say she dresses like someone who has put on a fair amount of weight and does not yet know how to dress for it. She is far from fat, but she needs to dress her body (and her age) better. She looks rough.

      • LadyKateC

        Yes, feeling much sympathy for Deborah over here. I had a baby last year and I am still trying to figure out what to wear. It is a lot more limited than it used to be! Of course, I have a lot less money and no access to stylists, so I am not sure what happened here.

    • RuthGo

      I was thinking the same thing. Back in Will & Grace days, she was one of those women who was totally flat and could wear those plunging necklines and always look chic. But her body never went back there after her pregnancy. To her credit, she seems aware of that but has never figured out what to do with a body that’s curvier and heavier than it once was.

  • Clydette Wantland

    I could forgive the dress is her hair wasn’t in that bun! Knot head.

  • Sara__B

    That’s SO not her dress, hair, and makeup that it doesn’t even look like Debra Messing any more.

  • Not applicable

    she seems to be in crisis.

    I mean, I get it, not so long ago you were younger and MUCH thinner and could rock just about any look. Now…things have changed, can’t fight the bulge (honey, I’m speaking from FIRST HAND experience) and your face is just round… oh, it’s tough to own.

    But- Deb, honey, you are still GORGEOUS! come on girl- never been a better time to be curvy. Let’s get back to the basics- play your strengths.

  • MoHub

    She’s turned into a Kardashian.

  • Janet B

    His makeup is much better than hers.

  • stubbornthoughts

    You know things have turned bad when Debra Messing – of all people – gets hits with the ugly stick on the red carpet.

  • Diego!

    Oh no… I threw my coffee in a basket when I saw these pictures! UGLY!

  • Winter_White

    Wow, this is exactly how I pictured Grace Alder’s Aunt Pesha! The one who perfected the Eye of Shame.

  • Adelaidey

    Way harsh, Tai. It’s not thaaaat bad.

  • Miss_Led

    These pictures will now be placed in the dictionary to illustrate the word “Unflattering.”

  • l_c_ann

    No, really, who is that?

  • bertkeeter

    Her head looks huge with that little knot on top!

  • par3182

    Cue Karen Walker: “Oh honey…what is this?”

    • Geoff Dankert

      “Honey” … (finger waving up and down) “What’s going on? What’s happening?”

  • TAGinMO

    Remember when we all used to gather ’round the comment section and complain as one with TLo that Debra’s hair had been the same FOREVER and she desperately needed a change?

    Good times.

  • Mary229

    I always thought she was such a beautiful woman. She looks like she’s had work done. :(. Why?????? She was pretty as she was!

    • mhleta

      She might have had Thermage done on her face. It can make your jaw swell a little. If it’s gone in two weeks, we’ll know that’s what it was.

  • mhleta

    I’d like to ban satin forever. Double that for black satin. It’s the rarest of women who can wear it without looking like she should be serving canapés at the Rocky Horror mansion. Here the shine adds volume and the black lends a dowager quality, a criminal thing to do to a woman as beautiful and vibrant as Ms Messing.

  • histrogeek

    She looks like she’s going for an Adele look. Not sure why Messing would want that, but oh well.

    • AshleyDeHaye

      Because Adele is the only woman with a regular body type most of these people know.

  • Yeah. That’s just bad. I love her. But that is not her look. She is such an exquisite creature but time for a new stylist.

  • conniemd

    Hair – check, make-up – check, – dress – check, accessories – check. ALL BAD. I would never, ever have recognized her.

  • Mismarker

    This is a visual representation of the debacle that was “SMASH”.

  • ConnieBV

    Debra, honey no.

  • Myrlin

    That’s a very sophisticated look for the sixth-grade formal.

  • Fordzo

    She thinks she is Lucille Ball, that’s all I can make of it.

    • Patricia Gillett

      I think you nailed it. That must be what they were going for here. And missed. Badly.

  • Ben Smith

    Oh honey, no. You look like a drag queen. A BAD drag queen.

  • formerlyAnon


    • BrooklynBomber

      Ha! I don’t know why, but that made me laugh out loud!

  • Patricia Gillett

    Oh dear. How many events in a row is this that we Bitter Kittens have just told her to go home and start over? Five? Not a good trend.

  • alwaysanswerb

    That… is basically my prom dress from 10 years ago.

  • blueberrypanckae

    She is sinking slowly into Kirsty Alley territory…a cautionary tale….

  • River

    And the makeup is bad and her shoes don’t fit and…poor dear.

  • MilaXX

    I really think the problems with her dressing lately are because she cannot figure out how to dress a 40 year old body. It’s a shame really because she is still as pretty as ever, she’s just not 20 or a size 2 anymore.

  • I can’t even get to the dress. That is not her hair.

  • LaSylphide

    Why does she have a cinnamon bun on her head?

  • MaggieMae

    It’s so aging. I think she could pull off a sexy retro look, but not so literal. Come on, Debra! You can do it!

  • epenthesis

    Almost like a Halloween costume.

    I usually don’t comment on accessories, but that little bag made me think of an anthropomorphic dinosaur in, say, The Far Side, trying to carry a dainty human-size purse.

  • unbornfawn

    Not her look. How does she not see that? The white version looks styled and ready to go for Taylor Swift.

  • MandyM

    That’s Christina Ricci’s dress. Or maybe even Selena Gomez. The hair is doing nothing to flatter her face, I love her but I agree that this is not a good look on any level.

  • sk8tfan

    I can only assume that her gay was kidnapped and instead of cash,
    this was part of the ransom she had to pay.

  • nannypoo

    This could be a contender for the Worst list at the end of the year. Horrifying.

  • stephbellard

    It’s like she decided, I’d really rather look heavier for the Tonys.

  • LANDRU3000

    It’s the hair that totally ruins it. I think she was probably trying for Margo Channing but didn’t want to be too literal.

  • Cameron Turner

    Come on Grace Adler… you are better than this!

  • Damien W

    She’s getting advice from the wrong Will now.

  • Cloveradams

    Good lord, she looks like a prison matron from a 60s-70s “Girls in Chains” movie, all dressed up for the annual dinner of her penal colleagues.

  • AutumnInNY

    She’s either gained weight or this just adds pounds but TLo you are correct. I can’t remember the last time
    she looked good on the red carpet. And cap sleeves are tough to pull off, very few can. Nicole Kidman, the First Lady are two off the top of my head that have the arms for it, for the rest of us-find another option.

  • Anniebet

    That’s possibly the worst bust line I’ve seen on a celeb in, well.. ever? She almost looks deformed in the last pic. So much wrong here, it’s sad to see. I have a soft spot for redheads, but here she seems to be going for the “bloated debutante” look.

    Dang, did I just say that?

  • JuliaInBlack

    Bless your heart, Debra.

  • ashtangajunkie

    Oh, I’m sad now. Debra Messing’s dress has made me sad and her painfully tight-looking bun has made my hair hurt.

  • demidaemon

    What’s worse? She took a bridal dress and ordered it in black. If that doesn’t say something about her subconscious, I don’t know what will.

  • JP

    I’m so tired of lady starlets squeezing into shoes that clearly don’t fit as well.

  • Rand Ortega

    Maybe when I stop laughing/crying/screaming/choking from all the comments, I’d just like to say while I agree w/ TLo that the dress is a bit young for Ms. Messing, the problem might be the fit? It looks a bit large for her, particularly in the shoulders & waist. Unfortunately that lends to the whole Laney Kazan/Benjy’s mother in “My Favorite Year” vibe she’s throwing off. Not very flattering.

  • PrunellaV

    Also, her face looks positively stuffed with fillers.

  • Rand Ortega

    Those shoes are waaaay too big. Look where her toes are.

  • kimiakay

    Does she not look like “Jane” of Mad Men, Roger’s almost ex-wife? Only in the face, of course. But when I saw the thumbnail I didn’t recognize Debra Messing. I know she’s gotten older (who hasn’t) but boy has she changed. She never seems happy anymore.

  • D J H

    If I were a often-photographed actor or star, my goal in life and public appearances would be to never make Tom and Lorenzo say “Sweet Jesus on a breadstick!” when looking at a photograph of the clothes I’m wearing.

  • kim bunchalastnames

    it’s a big drag queen not.

  • Christine Marie

    In all fairness, this didn’t look nearly as unfortunate in person. Although by the time I saw her at the after party, she apparently was over those shoes, as she was walking around barefoot.

  • pattycap11

    it doesn’t matter about the weight, at all. but she looks kind of insane here. so that’s bad.

  • Tigerfly

    If she has them, her gays obviously hate her.

  • Eovaai

    This is so bad it’s hilarious.

  • Lisa M. (ReVoir) Kramp

    Holy wow. I didn’t even recognize her!

  • Mary Stone

    Dear Lord, it’s Yaya at the big, fat, Greek wedding…It really is aging and unflattering, making her look much heavier/shorter than she is.

  • quiltrx

    I love the dress…and I have to say that a bigger woman *can* pull this off if styled correctly (see Lisa Lampanelli ‘before’ pictures). But boy, this styling makes my eyes itch.

  • Judih1

    First example I’ve seen where wearing all black is NOT slenderizing.

  • Oh…my god…

  • e jerry powell

    Oh, dear.

  • Is she preggers? Since when is Debra Messing a “bigger” woman?!

  • Fred Vaughn

    I wanna like this, but I have to agree that something looks off about this…

  • Contralto

    Oh honey. No.

  • bellafigura1

    I mean, let’s just accept the terrible, awful, no-good dress. And the shoes that don’t fit. And the silly purse. And ok, the garish makeup with the corpse-lip (I’m afraid to look closely, is that brown lipliner?). Fine. THE HAIR IS TERRIFYING.

  • ZnSD

    Oh girl, NO.

  • Gingerella

    You queens are mean. She isn’t your Gracie at 34 anymore! She looks awesome bitches