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In or Out: Debra Messing

Okay ladies, here's a puzzle for you.

How do you go from this...
Debra Messing attends the premiere of "Whatever Works" during the 2009 Tribeca Film Festival at Ziegfeld in New York City in Donna Karan Pre-Fall 2009 this?
Debra Messing attends the CHANEL and Tribeca Film Festival Artists' Dinner at Odeon in New York City wearing Chanel Spring 2009

Let's move in for a closer look:

Great color, dress fits her like a glove. Shoes are just okay, but at least they're inoffensive and they go with the outfit. Hair looks great, makeup is fine (except for the furry eyes she always does).

Moving on...

The dress is AWFUL. It does nothing whatsoever for her figure and the jacket actually makes it look worse. We never thought it would be possible to look bad in Chanel, but she managed to pull it off. The shoes are cute but they look like they're a size too big and when you're wearing clunky shoes to begin with, that makes it even worse. But WHAT is going ON with her hair and makeup? How is it that she looks ten years older all of a sudden?

And we hesitate to say this because we really do try and stay away from body issues, but Debbie honey, what is going on with your knees there? Were you gardening all day? They look bruised and battered. If you're not going to wear hose (and the more we look at this, the more we think a colored hose might've helped the look), then at least wear a skirt that covers them up, girl.

[Photos: Getty Images/WireImage]

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O to the U to the T. It takes work on someone's part to make a pretty woman look so spinster.

I am back to TOTALLY agreeing with TLO.

I loved Debra's little red dress ... she can be hit and miss and sometimes too severe in her choices.

Which is why I loved how she glammed out in the DK outfit. Looking youthful and sexy, without trying too hard.

But then she does that Chanel thing, too severe and trying way to hard. Almost nothing works, though she trying to do Chanel for the Chanel movie. But maybe that was the problem? Went for a concept but got sidetracked somewhere?

Just puzzles me to no end as well. What was she thinking? And did she take a loot in the mirror before she went out?

Just sayin and agreein again-

The hair in look 2 seems to be a modified Marge Simpson.

But the shoes in look 2 - yowza, I want those.

"Brooklyn Bomber said...

The hair in look 2 seems to be a modified Marge Simpson."

ROFL. She looks ridiculous!

Ugh. I'm tired of her.

I like the first one. It is typical of her "sexy" Debra look.
But I'm going out on a limb for the second look. I like it. For a short dress, I like loose and unfitted, it doesn't look desparate or too young. The hair I agree is off, too tall at the top. A regular pull back would have been fine. And yes, the make-up is too harsh.Overall IN.

Alas, red carpets do serve a purpose. Red carpet=healthy glow on hose-free legs. Black carpet=Bad shadows and the appearance of someone who took their first rollerskating lesson in a used car lot the day before.
The shoes, though are wrong, I think with that dress. I like the rest of the look. So, she doesn't want to be a vamp everyday.

Man, I'm trying to muster up some enthusiasm here. Nah, I got nothing.

I can see why she thought the Chanel was a good idea. And I like, if not love the shoes. The hair and total lack of body english (if the shoes are why she's standing stiff as a board, they are a bad, bad mistake) are what ruin the chance to make the dress fun and witty. I find it very easy to imagine a pose, perhaps with the hat or gloves that the outfit would get in a fashion editorial, in which she'd look elegant, fashionable and dead on.

That pose, however, can't be held indefinitely, one has to move, stand, sit, etc. to get through life. Hence awkward moments, not the vision in somebody's head. I am convinced she (or her stylists/fashion advisors) choose outfits that she likes in her head, without being able to really envision what they will look like as she moves through the evening, or how to make them work. Since that's what you pay the fashion help for, perhaps it can be laid at her own door, otherwise she's flushing money down the loo.

I Agree that she looks 10 years older in #2. But why does she look so mono-chromatic in look #1? Is it her foundation? her lack of blusher? her beige lipstick?

Look #1: She looks like she needs a blood transfusion - STAT!

Look 2: She's channeling Lucille Ball, no?

Maybe this has always been the case, but why is it that so many top celebrities are wearing clothes that do not fit?

How does this whole celebrities getting loaned clothes work? A well known person can't get something fitted to them? Can't people afford their own wardrobe anymore? Can anyone explain?

flamingjune said...

Look 2: She's channeling Lucille Ball, no?

You read my mind.

She looks like Frasier's wife in that second outfit.

Yes, the red dress was right and perfect for the occasion. But she has to change her looks in order to not repeat herself. I don't believe the Chanel is awful. Black hose and killer black pumps would have youth-enized her 2nd appearance. However, that has been done to death already with celebrities. I like her effort for trying and (hopefully)learning.


Look 1--Typical Debra.

Looke 2--Lose the jacket and fix the hair, and it would probably work. Granted, she needs a pair of shoes that fit, but I like the style of the shoes, and they go with the dress..

I actually think the first look is pretty awful too. She's either too old or too thin (or both) for that deep V neckline. The second outfit looks like she's on the way to a nurses banquet. Are we likely to see many more outfits with neck bows and 3/4 length sleeves, thanks to Michelle Obama?

I don't know if it the length, perhaps the collar of look #2, or the angle of the photography, but she has never looked that short to me before.

The dress itself isn't awful, but it just isn't right for her. Look look #1, though.

Look #1 is nice.

Look #2, I like as well. Shoes are beauts.


oh dear lord. OUT!

That Chanel is horrible. She looks like my aunt Vera.

Lulu said:
The second outfit looks like she's on the way to a nurses banquet.

Eureeka! That's it! I knew it reminded me of something. all she needs is a big red cross on her cape, and a little white 3 corner cap!

i like the first look, but it seems there was a fitting problem at the boob area. I think the main problem with the second look is the hair, too severe, it throws everything off somehow.
I laughed when you mentioned the knees thing, because on the weekend I read this (she said it at the event she was attending).

“When I’m on the floor with my son — Look at my knees, do you see? Majorly skinned knees," she pointed out to OK!. "That’s from my son’s birthday party on Saturday at the gym and I was crawling on the floor. Skinned knees and chasing after a little boy keeps everything in perspective.”

so, there you have it, it was a mom problem :-) and maybe it was too late to change outfits for that event.....

Call me crazy but I think the Chanel is cute and those shoes are to die for.

Totally with you on both looks. Like Flamingjune, the first thing I thought of when I saw the Chanel was "Hey Lucy, I'm hooooome!" Who would have thought Karl Lagerfeld had a flop like that look in him? And the shoes look like Minnie Mouse shoes.

She really needs to lose the Rachel Zoe eyes. Way to harsh and aging.

Looks like she was going for Audrey Hepburn and failed. Out.

Look 1 - tasteful, elegant, good fit, six thumbs up.

Look 2 - OUT TO THE MAX. Oh, dear, where to start? Shoes - not just Minnie Mouse, but 1930's nursing shoes gone horribly wrong. The dress has a collar that is far too wide - rather than laying close against the neck, it's a huge hole in which the neck looks like a planted pole. Plus, the baby doll dress doesn't flatter at all. Jacket - how depressing. Either cut or mis-worn too wide at the neck.

No socially redeeming value here at all.

Twelve thumbs down.

Time to return to Rachel Zoe.

Anonymous said...
Time to return to Rachel Zoe.

4/27/09 1:29 PM

That's part of the problem.

Love the first dress. The nude lipstick and center hair part are not helping her overall look, though.

How come someone like Drew can get away with a "character" look, but it looks ridiculous on Debra?

too many cats

She's 41.

Now, what is age appropriate?
You'll never see that white Chanel on DM as an answer.

At least her finger and toe nails aren't black.

god, she looks terrible in everything and i am tired of seeing her. her makeup in the first look is her typically offensive raccoon rachel zoe variety, and that dress is disgusting on her because of her man chest, complete with nasty oilled up clavicle.

the second one is less offensive to me, i think she looks more fun than usual, like she had fun with her look. does a person have to wear skintight chest bearing dresses everyday to be fashionable? it's a decent enough frock.

the hair, however, is reminiscent of le tragique sarah jessica parker updo of yesteryear.

ugh! i'm so done with this bitch!

Yeah, that second look is pretty bad. I don't even like the shoes. Blech.

Aw, TLo, I must respectfully disagree about the second. I think she looks charming.

Except for the knees. THAT I agree with.

Red: in

B&W: out



In and out!
God, that Chanel outfit is hideous.

I like the Chanel shoes, but that's about it.

OK, here's the explanation:

"...the 40-year-old The Starter Wife star said that son Roman Walker, 5, keeps her real. “When I’m on the floor with my son — Look at my knees, do you see? Majorly skinned knees,” she points out. “That’s from my son’s birthday party on Saturday at the gym and I was crawling on the floor."

another laura

Out and Out. I don't like that red dress, either.

I gave up on her. Seriously.

#2 - She looks like a porcelain doll. So not sexy, not that you have to look sexy all the time, but that is some dowdy-looking number.

I love the Donna Karan dress and shoes. I love that shade of red. The makeup is awful, though.

Totally off-topic, but Hedda Lettuce is on the Tyra Show today, in one of her experiment episodes, this time called "The Gay Kingdom." Um, I'm excited to see Hedda, to say the least! :D

I'm kind of a fuddy duddy, but I really think that loose dresses should be combined with a tighter jacket or cardigan (gasp!)

If you're going to wear a loose jacket, it's best paired with a tailored shift underneath.

If the jacket had been a little longer, she would have passed for a Supreme Court Justice.

I think she looks like a 1970's streetwalker in the red dress with the neck cut down to the waist. I LOVE the CHANEL! It's kooky and cute-- the whole thing-- even the Minni Mouse shoes and the fuzzy top knot hairdo. It arty oddball and I think it totally works.

I dislike her makeup in both outfits.

I can't help but think a neutral eye and a dramatic red lip in the first dress would make the look even hotter.


Oh, dear Lord...OUT and OUT.
Her boobishes are non-existant in the red get up. Bony chests in low cut dresses are fug.
As some others posted already, Nurse Ratchet is alive and well in the second look. I am officially sick of Ms. Messing........

Who the hell cares about Debra Messing; rip SJP's latest getup she wore to the opening of her "husband's" revival "The Philanthropist". They're both awful!

I never understand why she constantly wears dresses cut down to the navel. It looks terrible on everyone and draws the eye down away from the face.

Maybe she thinks she is old enough for the Laura Bennett "older woman" aesthetic.

I think what makes Debra look severe is the hair do... It does look like Marge Simpson or Amy Winehouse's infamous beehive hair...

I personally think the dress is cute (although the color is off), and the jacket looks quite sophisticated... Although I have to say that I hate the clutch and the shoes...

Ditch the clutch and the shoes and the make up and the hair do... She looks just fine...

Say what you will about "Rachel Zoe" eyes, Rachel Zoe turns out perfectly gowned women who are feminine and stylish.

Rachel Zoe would NEVER let a client go out looking like a clown, which is what look 2 here does.

I totally disagree with your assessment-- I think she looks FAR better in outfit #2. More modern, less tiresome Hollywood sex kitten. (Okay, the shoes are too big, but that's nitpicking-)

It may be more modern, but that doesn't excuse the bad fit. The neckline looks like something for an obese woman, with Debra's neck sticking out like a skinny stalk. It just doesn't fit at all.

Second, either the jacket is cut badly, or Debra is deliberately wearing it pushed back to expose the entire bow -- throwing off the lines of the jacket. The jacket should be well-fit through the neck as well, and the bow either covered or pulled out on top. This poor attempt to match a very tailored dress neckline with a very unstructured jacket neckline just does not work.

Also, it is possible that the jacket is the wrong size. When a jacket leaves that much of the wearer's chest and stomach exposed -- i.e., doesn't even go around her -- a larger size might be needed. Part of this pulled back look also could be caused by the jacket being too small through the shoulders, which generally causes the jacket to pull too far open when a broad-shouldered wearer stands up straight.

As well, the length of the jacket arms is unflattering. The sleeves either need to be shorter or longer. Here, where the sleeves hits her, they make Debra look like she's in an out-of-style thrift shop purchase with previously shortened sleeves for a minature woman.

Plus, the silk dress is just totally wrong for her figure. Perhaps a skinny waif could pull this voluminous look off. Debra, however, is not a waif. She looks like she's got a huge silk parachute hung from her shoulders.

And the hair. God. The squirrel's nest in my front yard's tree is neater-looking than that.


It looks like she just grabbed some mismatched pieces from SJP's closet and tossed them on, hoping the press would laud the kitschy, kooky look.

Tsk tsk, Debra. We need to tawk, honey.

Never have been on the Debra Messing bus, just don't get it at all. She's alright, she's pretty but I don't see the charisma or attitude that would make her fun to follow.

If I were TLo I could find a much better way to write this, by the way.

TLo, since you don't have to wear those awful punishing shoes that are IN now, let me explain. Any shoe with heels that high will allow the whole foot to slide forward, pushing the toes against the front of the shoe. This leaves a space in the back, and crams toes out the front of many sandals. And I am sorry, but putting high heels on a grandmother shoe does not make it attractive on anyone. UGLY, just like that whole second look. Head to toe, it was a disaster! And her knees are starting to give away her age, crawling around on the floor or not. I really liked the red dress and the hair in the first look, except for the poor fit around the boobs. She is just so inconsistent.

I´d say IN in the first look and a big OUT in the second.

On the second look she looks as if she´d be wearing a child´s dress. It looks odd. How come someone in her 40´s is trying to go back to kindergarden??? Mmm Debbie... you miss it here.

On the other hand, she looks stunning in that red dress.

Out. Lay off the coke, Deb.

I think she looks good (in both), as always.

You obviously don't like Chanel very much because you are criticizing the designs?
SHE DIDN'T DESIGN HER OUTFIT. think about that?

Also, the "furry" eyes is eyelashes, not fur.

I think look 1 is sexy and look 2 is sophisticated!

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