Debra Messing Style Double Shot

Posted on May 08, 2014

First, the good news. Debra finally figured herself out:

Debra-Mesing-Kaufmanfranco-Gucci-Double-Style-Shote-Tom-Lorenzo-Site (1)Debra Messing attends the 2014 “Spirit Of Life” Awards Luncheon at The Plaza Hotel in New York City in a Kaufmanfranco dress.

Debra-Mesing-Kaufmanfranco-Gucci-Double-Style-Shote-Tom-Lorenzo-Site (2)Kaufmanfranco Spring 2014 Collection

Debra-Mesing-Kaufmanfranco-Gucci-Double-Style-Shote-Tom-Lorenzo-Site (3)

Debra-Mesing-Kaufmanfranco-Gucci-Double-Style-Shote-Tom-Lorenzo-Site (4)

The dress is not super-great (we’re not sure any non-model human can handle that many lines and angles at once) and the shoes are a little focus-pulling, sure. But everything north of her shoulders looks pretty spectacular. And besides, we’re  not mad at the dress. We can live with it. It may be a little complicated but it’s practically streamlined compared to some stuff she’s worn.

No, this is all good.

But listen, don’t pop the corks in celebration just yet. This happened in the same week:


Debra-Mesing-Kaufmanfranco-Gucci-Double-Style-Shote-Tom-Lorenzo-Site (5)Debra Messing attends “God’s Pocket” screening at IFC Center in New York City in a leopard-print blouse paired with black pants and a Gucci belt.

Debra-Mesing-Kaufmanfranco-Gucci-Double-Style-Shote-Tom-Lorenzo-Site (6)

Debra-Mesing-Kaufmanfranco-Gucci-Double-Style-Shote-Tom-Lorenzo-Site (7)

Debra-Mesing-Kaufmanfranco-Gucci-Double-Style-Shote-Tom-Lorenzo-Site (8)


We will stipulate that there’s nothing horrible about this outfit, in theory. We think there are plenty of real-world settings where these items would look great on the right lady. We even think Debra might be one of those ladies. We just don’t think it’s something that looks great in photographs. There’s no way a blouse like that could look anything but kind of dowdy and aging in pictures. Put that blouse with a pair of light-washed skinny jeans stuffed into knee-high chocolate brown boots and any gal would have it going on for real. But you pair it with vampire makeup (Debra, what is going on there?) and an entirely nondescript lower half, and the whole thing looks funky in the not good sense of the word. Our work here is not yet done, kittens.

That is some seriously bad makeup.

Someone once told her her eyes look squinty in pictures and she never got over it, did she?




[Photo Credit: Astrid Stawiarz/Getty Images, Ben Gabbe/Getty Images, IMAXTree]

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

  • lundibleu

    I think she’s been speaking to Amy Adams about hair and make up. Well, for the first look anyway.

  • lexilexi

    I think she’s showing off her new svelte figure.

    • kimmeister

      Hello, thigh gap.

  • Glam Dixie

    Outfit number 2 is obviously for her Grand Ol Opry debut later this afternoon.

    • Belvane

      Damn! I had that right at my fingertips but you beat me to it. Now I’ll just have to settle for an Altman “Nashville” reference.

      • FibonacciSequins

        I was thinking an ABC “Nashville” reference, as in Rayna James.

        • charlotte

          You and me both.

          • Judih1

            Yep that is some Rayna James realness there

        • berkeleygirl

          Well, in real life, she does sleep with Luke.

          • FibonacciSequins

            OMG, I had no idea! It all makes sense now. lol

    • Artesian_Belle

      Debut or retirement party?

    • Emily Smith

      I was going to say that outfit #2 was CLEARLY stolen off a costume rack for the Rayna James character on Nashville along with the card indicating all the styling details. I mean it’s bang on Rayna.

    • StillGary

      If this hadn’t been a double shot I would have swore it was Shania Twain!

  • Anna

    Debra Messing, Mob Wife.

  • smh4748

    The second look is very Shania Twain.

    • StillGary

      Ya beat me to it

  • YourBaloneyDontGotNoSecondName

    I’ve always loved her but now I love her for different reasons. She gives Crazy Eyes like nobody in the business. Things like that are important to me.

    • Danielle

      She was present for the lesson on smizing.

      • Sarah

        Smizing like brains are your favorite food and you’re about to get some, maybe.

        • Glam Dixie

          Omg, Sarah, that’s the funniest thing I’ve seen all day!

        • demidaemon

          Exactly how I feel. SCARY CRAZY EYES.

    • kimmeister

      The closeup in look #2 was giving me Catherine Zeta Jones crazy eye.

  • juniper

    the second picture of the second outfit looks like Catherine Zeta-Jones. WTH

    • kimmeister

      Whoops I didn’t look below before I wrote the same thing.

      • juniper

        it’s reassuring to know I wasn’t the only one!

  • charlotte

    How did she age 15 years within a couple of days (or rejuvenate, depending on which event happened first)? That is some terrible makeup in #2.

    • Rhonda Shore

      And that orangey hair color…what’s wrong with a rich chocolate brown?

  • FibonacciSequins

    That makeup in #2 is so harsh and colorless at the same time. I don’t know how she achieved that.

  • hughman

    “Mom, this is my bachelorette party and you are not our age. No one believes GG stands for “Goodtime Girl” and I’m telling you, you can’t ask to do body shots off the security guard even if he did pretend to card you.”

  • bunnydiet

    Am I the only one who notices how much weight she has lst? She looks great!

    • lexilexi

      I noticed, and I agree. She looks fab.

  • Joanna

    I don’t know . . . I don’t think the second one is that bad. The biggest problem there is the make-up, which I agree is HORRENDOUS.

    • Tatiana Luján

      I love the pants.

  • TwiddlyStun

    My quibble with the dress is it does less than nothing for her bosom – as in, it must be making it look worse, because I can’t make sense of it.

  • sienna elm

    I like the dress – and I’m really glad they seamed up the front of it.

    Weird hair in the second one!

  • AlexisPayne

    I’m sorry, that second outfit is pure Grace Adler.

    • demidaemon

      That’s probably exactly why she picked it.

  • marlie

    North of the neck in the first picture, Debra looks lovely. The same region in the second photo? Girl, I don’t even know what to say. Both outfits are “just ok” to me.

  • decormaven

    In the first look, if the shoes were less complicated, a killer color had been applied to the toes, and maybe a bangle was dangling from the wrist, I’d say this would be a great style for her. That second look scares me- both the makeup and the outfit. She’s got the goods to be a gorgeous gal, but she needs someone to help her hit the marks consistently.

  • Man Dala

    I like the first look. She always goes for plunge neck lines (as her character in Will & Grace often did) and that’s a good look on her, and better yet now she’s lost heaps of weight. I hate when she does those crazy eyes (see second photo of the second look). She does that a lot on the red carpet.

    • Grumpy Girl

      One of my coworkers told me that the look comes from eyelid-lifting surgery. That was her excuse anyhow, and she called it on anyone she saw with it (IRL more than celebs).

      • jay

        see, I tend to make crazy eyes when I’m wearing WAY TOO MUCH eye makeup and am subconsciously convinced that I’ll end up with a giant mascara clump in my eyeball.

  • Janet B

    So much better than her recent history.

  • Tarquin

    Second look; Jackie Collins REALNESS

  • teensmom99

    Before I read this through, I was going to say “but I’ve been wearing (non-sheer) versions of the second outfit here on the east coast in this weirdly cold May weather.” So I do have sympathy because every morning I want to wear something springy and it’s too cold so I cleverly alternate between black pants and a black skirt which seem more spring appropriate than plums and browns . . .and then I have to figure out what top to wear. But then I read it and saw the TLO know and see all–I’m going to the office . . . not getting photographed, so I get a pass. Dear Debra should know better.

  • Valdri8

    In my opinion, she is like Christina Hendricks – she should never wear black on her upper half with her coloring; it looks like dog’s breakfast. They have so many colors that NO ONE ELSE can wear like chartreuse, for example.

  • KateMaryC

    She would benefit from Megan Mullally following behind her all of the time going, “Honey, no, what is this, what is going on here?”

    • Agnes Gooch

      God, I miss Karen Walker.

    • embers618

      Yes, this is exactly what I hear in my head whenever I see a picture of Debra Messing.

  • MilaXX

    I like the first look except for the too heavy shoes. I wish someone would burn that second outfit. It didn’t work on Kate Upton and I’m not liking it on Debra. I don’t hate the makeup in the second look, but I think the hair is a it harsh. Not everyone can do that combed back look.

  • icm

    she looks like a wax figure

  • Dagney

    I think she is a striking lady, but her makeup in these photos just looks, too “done,” too…cakey and eyelashy and highlighty or something. Seems like she would look ten times better with less.

    • NeenaJ

      It’s something with the eyebrows, too. Too harsh, filled in and not symmetrical – one has a pointed arch and the other is rounded. Not sure if she’s trying to give an eyebrow raise through the botox or they were just filled in wonky.

  • Lex

    Let’s put aside the horrific hairstyle and makeup (I agree they are dreadful): the dye job on her hair looks SO cheap! Looking seriously cheap and brassy… she needs to tone it down: more brunette less redhead. It ain’t working for her anymore, at least not this way. She should fire her hair and makeup people

  • demidaemon

    The eyes. I always feel like her eyes are going to pop out, fly through the screen, and attack me. There are crazy eyes and then there are CRAZY EYES. Debra has the latter.

    I don’t particularly love either outfit. The headsuit on look one is much improved though, but everything is wrong in look two. She looks like she walked off the set of Dynasty.

  • Agnes Gooch

    Oh, dear. There’s Botox and then there’s BOTOX!

  • LadyVimes

    Snaps for the first one, just…what on the second.

  • Anna

    Didn’t Kate Upton wear the second outfit a couple of weeks ago?

  • bitchybitchybitchy

    Debra’s first look especially her hair and makeup are such an improvement over some of her recent misfires. I don’t mind the dress, especially with a less open neckline.
    The second look, though, unnecessarily ages her, and that’s just wrong.

  • kcaza

    I suppose this answers the question ‘what would Rachel Reilly wear if she wasn’t Rachel Reilly?’

    I didn’t need an answer.

  • Swiftlytiltingplanet

    I’m always sad when curly-haired people straighten their hair more often than not.

    • Constant Reader

      Me too. Mostly because I then feel pressure to straighten mine, which I really hate doing.

  • CeeQ

    Aw SO.CLOSE. Sassy hair one day, yoga hair the next. SIGH.

  • DeTrop

    The dress on the model looks super. Of course, it’s unlined and not for real-world wearing. DMs is lined and it loses something. Anyway, what’s with all these heavy, clunky shoes? They do nothing but bring attention away from the clothes. U.G.L.Y.
    I like the second look minus the crazy eyes. She appears much slimmer since SMASH.

  • MarinaCat

    I don’t understand why she favors such heavy shoes with *everything.* It’s not even that all I see is shoes; all I see is FEET. I actually think the second outfit would be great for our casual Friday, but in winter. (Talk about a slimming outfit!)

  • holla

    Maybe if she had better hair, make up, and belt in #2, it would not be so off looking.

  • Wow, that’s a shocking difference between two photos, face-wise. These pictures should be excellent examples in makeup classes for the good and bad power of makeup, and how they can make a person appear radically different even in the same week.

  • Patrick Cleary

    The second look is that Executive Assistant on the top floor who reports to one of the C-suite people that nobody knows what he does, but she’s hilarious and always has candy on her desk.

  • ashtangajunkie

    If the first shot is Debra Messing, the second is her crazy-ass twin sister. That makeup and hair hurt me.

  • MaggieMae

    She is one of those people that I barely recognize, picture to picture.

  • That second picture is straight up 1992 Line Dancing Queen.

  • housefulofboys

    I guess I’m alone, but I don’t think that first dress is good for her at all. The proportions look off to me, like she’s all torso with short legs. It may be that it’s too big on her, along with the stumpifying effect of the heavy ankle straps on her shoes.

  • formerlyAnon

    I think the real issue is that the jeans + blouse erase her waist.

    Well, that and the print on the blouse. But not everyone hates animal print as purely and unrelentingly as do I.

  • SusannaGA

    The second look: Priscilla Presley circa 1988.

    • pdquick

      And that’s why it’s fabulous.

  • Leah Elzinga

    wow. that is… cakey.