Debra Messing in Christian Siriano at The New York Pops 31st Birthday Gala

Posted on May 01, 2014

Y’know… we’re just gonna say it: we have no idea why this woman has a reputation as a fashionista. We’ve covered her for years and we always come away thinking she has terrible instincts.

Debra-Messing-Christian-Siriano-New-York-Pops-Birthday-Gala-Tom-Lorenzo-Site-TLO (1)Debra Messing attends The New York Pops 31st Birthday Gala at the Mandarin Oriental Hotel in New York City in a Christian Siriano dress paired with Stuart Weitzman ‘Nudist’ sandals and jewelry by H.Stern, Peipers + Kojen, and Nina Runsdorf.

Debra-Messing-Christian-Siriano-New-York-Pops-Birthday-Gala-Tom-Lorenzo-Site-TLO (2)Christian Siriano Fall 2013 Collection

Debra-Messing-Christian-Siriano-New-York-Pops-Birthday-Gala-Tom-Lorenzo-Site-TLO (3)

Debra-Messing-Christian-Siriano-New-York-Pops-Birthday-Gala-Tom-Lorenzo-Site-TLO (4)

Debra-Messing-Christian-Siriano-New-York-Pops-Birthday-Gala-Tom-Lorenzo-Site-TLO (5)

Let’s start with the dress. It’s actually pretty great, although it’s too tight in the bodice and too long in the skirt, and we think she could’ve used some sort of thin contrasting belt to define her waist better. Still, it’s a good starting point and it suits her. After that, it all goes to shit. Seriously, those shoes? That hair? The earrings? There are not enough “Sweetie, no”s in the world. It’s all just way too much. Tone down all the brassy gold accessories, find a more delicate pair of shoes (maybe with a gold accent) and let your hair down. It’s all way too severe for a pretty little cocktail dress.

A thin patent black belt, gold sandals, understated jewelry and a blowout would’ve taken this to head-turning. As it is, it’s only managed to achieve “head-scratching” status.




[Photo Credit: Brad Barket/Getty Images, IMAXTree]

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  • In_Stitches

    I love the draggy JLo-ness of the hair, face and accessories. The dress is great, but I wish she’d swap it out for the body-con red dress the rest of the look is calling for.

    • StillGary

      My first thought was, you shouldn’t try a bun unless you JLo or a ballerina!

  • boweryboy

    She’s a hot mess of toe-up drag queen proportions. That hair is two different colors, and Mr. T is jealous of the amount of gold she’s sporting. It’s like she or her stylist didn’t even try.

    • demidaemon

      Mr. T, hahahahaha! It’s so true. It looks like she raided his house.

    • CakesOnAPlane

      “I pity the fool who puts on my jewelry! I pity the fool!” -one of the greatest thinkers of our time, Chandler Bing

    • Rhonda Shore

      All that matching jewelry is so Staten Island.

  • BitterOldQueen

    dear god no.

    • Flavia Pantoja

      For a second I read ‘dear GOLD no’ ! I probably was thinkig along those lines… 😉

  • @Biting Panda

    Much like SJP still dresses like Carrie, Debra still dresses like Grace, the later seasons. Always too much, always leaving you wondering who actually dresses like this?

    • Sarah

      My thoughts exactly. This look is super dated in a late 90s/early 00s way, which was her Grace Adler heyday. I remember Vogue featuring her on a cover and pushing her as a style icon, but I’ve never been able to see it.

  • SugarSnap108

    She has a rep as a fashionista? I had no idea. In my defense, I cite every photo of her I’ve ever seen.

    • AnaRoW

      The only thing I can think of is that maybe Grace was well-dressed. It’s like how SJP regularly appeared on everyone’s worst-dressed lists for years then got the role of Carrie and all of a sudden was considered a fashionista.

      • par3182

        Grace? Well dressed? Karen Walker would like a word with you.

        • AnaRoW

          It was just a guess. I, like SugarSnap, had no idea Debra Messing was considered a fashionista. Honestly, I can’t remember how Grace dressed.

    • holla

      maybe as an example in the DON”T column?

    • StillGary

      Yeah, never got fashionista but i believe she has the best hair in business, if not the world!

      • DuBey2

        Precisely. Hair which should NOT be glued into a boring bun.

  • Nikko Viquiera

    Honey…What is this? What’s going on? What’s happening?

    • Julie Chase

      HA! Karen would definitely not approve.

  • Jeremy Thomas Porta

    I think that reputation comes from being a skinny white woman best known for her work on a show about gay people.

    • holla

      hmmm that is in line with why JSP is also considered a fashionista.

      • alyce1213

        “I’m not a fashionista but I play one on TV…”

  • IMNAngryLiberal

    Also, and I say this with love, Deb tends to go all crazy-eyes on the red carpet. She has been doing red carpets for years and years .. you would think she would be used to cameras at this point.

    • demidaemon

      Maybe they are a sign of what lies within and she just is unable to restrain it.

  • Betsy

    Is this a joke? Really. This has to be a joke, right?

    • demidaemon

      I feel bad for Christian. That dress did not deserve THIS.

  • Janet B

    No, no, no……

  • Jessica Freeman

    It’s such a shame because she is a gorgeous woman who consistently fails to shine.

  • rebeemoon

    Oh, I don’t know. I haven’t seen her look this good in awhile. I don’t like the shoes, and I agree a blowout would have improved the hair. But I like the dress–and the earrings. So there.

  • GillianHolroyd

    The sheen highlights the weave of the fabric which looks like the material rice sacks are made from. And the cut, sorry, the horizontal bodice lines and the flare at the hips are doing her no favors. She needs some emphasis at the shoulders to balance out the proportions. Leaving her hair down might have done it.

    • kimmeister

      Yeah, I was just thinking the same thing about the textile.

  • CB

    She has a reputation as a fashionista? News to me…

  • Terri Terri

    And she is so beautiful, in my opinion. She deserves to look better!

  • kmk05

    The hair and the three-too-many bangles are the worst. No wait, I forgot the shoes. I might have been able to forgive the earrings if they had been framed by blown out hair.

  • elizabethann1

    She ALWAYS looks terrible. Always. I don’t get it. How can she mess up such an amazing dress?

    • myandyleigh

      The sad thing is, the dress just disappears amongst all the tacky gold accessories, that hideous bun and those awful shoes. It wasn’t until I looked at the dress on the model that I even realized what the dress looks like, so distracting are all the trappings. Who could look at that dress and those shoes and think that pairing was a good idea?

      I used to think she dressed badly to just get attention. That might be true, but this is a whole new level of fugly that can’t be explained by attention-seeking.

  • She always floats near the top of my irrational hate list.

  • Gatto Nero

    She looks like the evening hostess at a restaurant of indeterminate ethnicity.

  • Kitten Mittons

    When I went from the blandness of Biel to that first picture of Debra wearing her crazy eyes and every gold piece of jewelry ever made, I was understandably stunned. I had to close my browser and collect myself.

    It’s all way too much. Just way too much on every front. I still prefer it over Biel’s Boring, Basic, Bland Beigeness. Give me Messing’s Maniacal, Meretricious Mess on most days.

    • Kayceed

      Let me fetch the smelling salts for you my dear.

      • Kitten Mittons

        You are a true friend.

        • Kayceed

          One must find ways to cope with unexpected shocks to one’s aesthetic sensibilities. And it is a wee bit early for a cocktail.

          • Kitten Mittons

            Yes, my boss frowns on day-drinking at my desk. I’ll try to limp along with some tea.

          • demidaemon

            He should be more understanding. I mean, look at what Debra forced you to look at.

          • Kitten Mittons

            If he only understood my side of things….

    • kimmeister

      You’ve been forced into alliteration. I wonder if an upcoming post will make you burst out in onomatopoeia???

      • Kitten Mittons

        It’s a definite possibility.

        If I get to the stage of writing dirty limericks, please call the authorities.

    • demidaemon

      Loving the alliteration of awfulness on display.

  • formerlyAnon

    This is a poor way to showcase some damn fine shoulders & arms.

  • MissusBee

    Does that glazed donut do suit anyone (apart from 60s air hostesses)? Are women being told that it is flattering to certain face shapes (it isn’t)?

    I think we need some bun rules.

    • Imasewsure

      I hate hate hate that hairstyle on everyone… but I love to think of it as a “donut do”… it helps anyway

    • DuBey2

      “bun rules” Could be taken so many ways…

  • ashtangajunkie

    I fear that the bodice will split if she breathes. Bad instincts took down a beautiful dress.

  • Constant Reader

    I irrationally love Debra Messing because she (like me) is from the most tragique state in the union — Rhode Island. And I tend to love a little Carmen Miranda Realness. But I’m not sure I can sign off on this without the fruit turban. Commit or go home, Debra!

    • Kitten Mittons

      Oh, man. What a huge missed opportunity!

    • Gatto Nero

      Is she a Rhodie girl? I had no idea. She’s ditched the accent completely.

      • Constant Reader

        Yep. East Greenwich (so, fancy RI with a lot of people from elsewhere. You end up with less of an accent than in places with mostly natives). I seem to recall reading an interview with Debra where she talked about acting classes and having to learn to speak without an accent. It was kind of funny — in NYC with all these Northeasterners having meltdowns over the inability to say “dance” properly. 🙂

        • Gatto Nero

          That is funny. ‘Cause the native accent is hard core.
          At a scent shop in Provincetown, MA (I’m a fragrance fanatic), the proprietor told me that Ms. Messing is a frequent visitor, and that she asks to try niche and often “masculine”-targeted (though I know scent is genderless) perfumes. Maybe she has discerning taste in that arena, at least.

          • Constant Reader

            I agree, it’s hard to get rid of. Mine’s not too bad, but any sentence with too many Rs is a danger zone. At least one will be dropped. And when I’m really sick or tired, so I’m told, my accent gets quite heavy. I don’t think I’d ever be able to get rid of it completely.

          • Gatto Nero

            I grew up near Boston, so — I get it!

  • PlethoraofBooks

    I would like her to hire the costume person from The Wedding Date as her stylist, immediately. That would be great.

    • decormaven

      Aww, you just intoned one of my favorite chick flicks. My kingdom for anyone who can name the maker of that robin’s egg blue luggage she totes.

  • shirab

    You know what would be so fun? Have her and Jessica Biel swap outfits. Just to see what would happen.

    • demidaemon

      I think they both would look just as bad, just in different ways.

  • Frecks

    Obviously, the readership here strongly disagrees, but I LOVE draggy, over-the-top, costume-y jewelry. Besides, if anyone’s got a face not to be overwhelmed by bold jewelry, it’s Debbie Messing here.

    I wish she’d been wearing a matte gold sandal (which, I know, would have given TLo the vapors), but otherwise, this has a crazy-fun, retro-60s, Fellini film vibe and I am HERE FOR IT.

    Best she’s looked in ages, and that happy expression looks really genuine. The attitude is making this work for me.

  • Denise Rambo

    At least I don’t want to yell at her to COMB HER HAIR!

  • Jacqueline Wessel

    I love lots of jewelry, but even I know that this is too much and too ornate and too big for this dress.

  • Kaytee


  • Danielle

    Somewhere, Karen Walker is sighing into her martini.

  • marlie

    I love the dress, but perhaps not for her? And I love her hair, makeup, and jewelry (though she could have ditched one of the big cuffs). But there isn’t anything even remotely redeemable about those shoes.

  • LilyVanessi

    The shoes are tragic, King Midas would be embarrassed by that much gold and black nails – really?

  • MightyMarshal

    This is borderline a Bianca del Rio ensemble.

    • demidaemon

      Well, it’s not a boatneck or floor length….

  • Qitkat

    Have any of you ever been to one of those jewelry shows with items for sale from around the world? I think that’s where her stylist went shopping.
    Oooh,lookatthat! Ohthisisstunning! Let’stakesixofthose! Wait!thoseearringsarefabulous! Wonderful!we’vegotacompletearoundtheworldlookforsomeone!

    Now, who shall we inflict adorn with these?

    • demidaemon

      Accessory ADHD, right?

  • BlairBear

    I don’t find many people who are labeled fashionista all that stylish . I mean Kate Bosworth ? Sienna Miller? Cara ? Maybe if fashionista just means trend whore willing look like smacked ass for Fashion

    • holla

      please tell me you wouldn’t whore it out if the labels are knocking on your door with some free pricey swag? I think we all have a little bit of that whore-ish side for fashion. If every fashionista looks good in everything, we have nothing to bitch about. For the sake of learning, we have to have the good the bad and the ugly. Like movie scripts and casting, I am sure the idea of all those people look good on paper to some designer. Sometimes, the execution just doesn’t carry through.

      • semirose

        Oh we all definitely would, it’s just weird that the media labels those who go out a lot in their free clothes as fashionistas. I always see it as a difference between being deliberate in your clothing and accessory choices vs. wearing everything that’s thrown at you. Pretty star in a pretty dress does not equal fashionista and yet…

        • holla

          I would agree on being choosier, but beggars can’t be choosers and she’s no A lister anymore, so the options maybe limited. Also maybe it’s a ploy to stay relevant. Any publicity is good publicity!!!

      • BlairBear

        Not what I’m saying at all I’m just saying wear expensive free clothes poorly styled or in many cases in the wrong sizes or wrong cut for your body isn’t being a fashionista . Being a fashionista is about picking the right clothes and styling them right . Whether you bought them yourself or they were thrown at your feet doesn’t factor in

  • FibonacciSequins

    The shoes the model’s wearing are miles better than those clunky back stripper heels.

  • clatie

    I have a weird question – why are those called “nudist” sandals? that’s just not right.

  • semirose

    I kind of love those earrings but NOT with this dress and those shoes? Really? Her makeup looks like when I add in one element too many and have to restart (always inevitably when I’m running late) except she…didn’t.

  • bunnydiet

    On the positive side: she has lost weight and looks terrific!

  • 3boysful

    The child of a genie and Wonderwoman, dressed in a matador’s cape.

  • Scarlet39

    At least the makeup is better this time. That’s all I got…

  • DeTrop

    Great arms. That’s an achievement. I like the dress. Agree it should be shorter and the shoes should be given to Goodwill.

  • d4divine

    Where are my castanets?! #FernandosHideaway

  • Fuchsiaforever

    I screamed (out loud) in horror when I saw this. Way to ruin a gorgeous dress…. :/ OY VEY!

  • Fuchsiaforever

    And helloooo? She was never a fashionista! Who said she was a fashionista? No way!

    • alyce1213

      She did.

      • Fuchsiaforever


        • alyce1213

          She says (thinks) she’s a fashionista.

  • MilaXX

    She’s not a skinny 20something anymore and while she is no where near fat she doesn’t know how to dress this body. I think the hair & makeup are actually really pretty but they don’t go with the outfit. The dress I don’t think suits her at all & she over loaded it with too much heavy jewelry & the wrong shoe. The whole look is off balance. On the other hand, yesterday she wore a simple red skater dress and a pair of nice pumps on The View. Her hair was down & the only accessory was a giant cocktail ring. She looked fabulous.

    • demidaemon

      I think she has a tendency to overdo for the RC (whether with accessories or overly complicated dresses) when simple silhouettes and single colors, well styled, flatter her much better.

      *That sentence feels like a grammatical travesty.

  • shopgirl716

    Agreed that she is not a fashionista. I also hate the cuffs.

  • EEKstl

    I’m with you everywhere but the hair, which I actually like and which suits her. It’s all the dripping with gold jewelry that’s killing it for me.

  • ballerinawithagun

    Everyone has made every comment I could make, so I’m just wondering…What the hell has happened to Stuart Weitzman shoes??? They used to be the epitome of classy shoes. They actually made shoes that fit me and were relatively comfortable for high heeled shoes, someone there knew how to create a comfortable last. Not to mention they were still reasonably priced for a well made product. All of a sudden this year the shoes are as disgusting and trashy as everyone else’s. They no longer fit as well and are uncomfortable just like every other shoe company. And now to add insult to injury, they have raised their prices.

  • OffToSeeHim

    How exciting for Christian! Do you guys know how she happened to end up wearing his dress?

  • bitchybitchybitchy

    Yes to everything the uncles said-lose the shoes, softer hair would be ways to improve this look.

  • Scott Cooper

    She’s a beautiful woman, but one who hasn’t accepted that her thirties are a memory and fifty is on the horizon. Severe hair is not her friend.

  • Amy Lawson

    I’ve been wearing scrubs to work for too long because I think she looks fabulous. I even like the hair and earrings.

  • carpediva

    I don’t think those are Weitzman’s “Nudist” sandals, are they?

    The rest… I shall not speak of.

  • Erica Woods Tucker

    I was going to say this is the best she’s looked in a long time.

  • decormaven

    Very tough look here. Heading toward late Joan Crawford look, and that’s not good. Please don’t go there.

  • Looks like it was ripped out of the closet of one of the British “My Big Fat Gypsy Wedding” lady participants.

  • Those shoes really are appalling.

  • kim bunchalastnames

    nothing to add, except to say, damn, you guys are SO on point.

  • SissyLou

    All I’m sayin’ is she’s got the crazy eyes.

  • Ashleigh

    everything you said….and, I keep getting Vergara vibes from this

  • demidaemon

    Somebody has styling dyslexia.

  • Jessica Goldstein

    In the early days of Will and Grace, Debra had a look that fit the fashion times very well. Thus, “fashionista” status. Then she had a child and gained weight and suddenly had no idea how to dress her new body. Now she’s largely got the long and lithe body back, but fashions have changed, time has marched on, and she doesn’t know how to dress her 40+ age. I can sympathize somewhat, as I’m now 44 and am discovering that just because I CAN fit into the stuff I wore a decade ago doesn’t mean that I SHOULD. In this case, I’m OK with the hair up, but it needed to be up in a simpler style. All your other styling suggestions would have helped immensely.

    • Joanna

      Completely agree 100%. I’m on the other side of 40, as well, and the only thing I could think of is that even with all of the changes TLo suggested, that look is still going to be too young for her. She is so striking, and I like her acting immensely, so I’m routing for her to figure it out!

  • Dagney

    I love it all, except the shoes! huh?

  • ItAin’tMe

    The hair and the shoes make her more Lucy than ever.

  • YoungSally

    How are those sandals “Nudist”?

    • somebody blonde

      They’d look good on someone who was wearing them with nothing else?

    • saintebeuve

      I came to ask just that. Maybe because wearing them, you realize you’d look better without?
      ETA: Oops, never mind. alyce1213 cleared it up. Wrong name. Almost too bad – so much joke potential.

  • Trickytrisha

    Way to ruin a nice dress. She needs help.

  • LadyVimes

    I like the jewelry, but that’s about it. The fabric of the dress looks cheap.

  • lamh36

    I think it’s a residual effect from her Will & Grace years, when she actually seemed to dresses much more fashionably, IMHO. Also too, I found her clothing on Will & Grace light years better than her personal style ever was

  • Jacob Bowen

    Debra Messing wears jewelry like my drag alter ego…except those earrings are HIDDY.

  • Ron Zank

    Fashionista? Or fashionpizza? She ordered it with everything.

  • Ashleigh Taylor Davis

    …and she thought to herself, (while biting her bottom lip, and arching her eyebrows) “I will wear ALL THE GOLD”. Then she slapped her assistant and took a sloppy drink of her “lunch”.

  • DuBey2

    Love the dress. By. Itself. on. her.
    The coloring really suits her skin tone. Oh, and the skinny belt would be great. Everything TLo said. I WISH they would just come to my closet (though I’d be horrified by its messiness) and style me!

  • MissRiss65

    I thought she’d borrowed Darienne Lake’s shoes! Yuck!

  • Shug

    I love the dress and hair, but she needs to swap out the earrings for a statement necklace with clean lines and maybe a pop o color shoe.

  • johnny sudeste

    crazy eyes

  • samo_samo

    I’m catching up on TLo posts today and totally misread the title of this one as
    “DEBRA MESSING 31ST BIRTHDAY GALA”. That caused me to do a double take. It made me giggle. I must be tired. #readingisfundamental

  • Mrs. O

    The dress on the model is wonderful. The one she’s wearing looks like a cheap knockoff. Why is the pattern of the skirt skewed? And it is tooooo tight. What if she needs to take a deep breath? I hope those shoes are loaners, because Gramma Ruth is going to want them back in time for church on Sunday. She will also want the hair, the danglies, and most likely the walker you filched.

  • JynxTheCat

    man she dropped weight! Do we not think that early on in her public spectacle that she didnt get it right more often than not? I don’t really remember other than her having the rep that she did.