Kentucky Derby Ladies

Posted on May 07, 2012

Despite its long history and reputation for sartorial splendor, there’s a problem facing ladystars who attempt to make a day of it at the Kentucky Derby. You can dress in derby-appropriate attire, or you can have your picture taken on the red carpet. You can’t really do both without looking a little frumpy or a little inappropriate, depending on which way you decide to go.

Debra Messing in Carolina Herrera


See? Derby-perfect, but not exactly wowing them on the step-and-repeat. There’s a sharpness to this outfit, but ultimately, the column of gray with explosion of color at the top makes her look like a vase; an illusion helped along by the lines here, which are not particularly flattering to her. It’s a cute idea, but this thing probably needed a contrasting belt, not to mention a little more tailoring around the middle and a more substantial pair of shoes. The trick here is to look perfect for the derby without looking like the wealthiest lady in church on Sunday morning. For more on that latter point, we direct you to the following.

 

Ginnifer Goodwin in Preen


Totally choir director, amirite? With a soupcon of sister-wife?

Unlike Debra’s look, we can’t really sign off on any part of this one. It’s neither Derby-perfect, nor picture-worthy. It’s an awkward mess and it’s not helped by the shoes, which look a little heavy and the hat, which looks like it was retrieved from under a bed.

This seems like an interesting challenge for a celebrity stylist: how to dress someone for an event like this, where the dress code is important, but not always photogenic? Looking at these two extremes (one, a bit too refined and the other, a total mess), we wonder if maybe it’s impossible to be both appropriate and fabulous at the same ti–

 

Mary J. Blige


Oh. Right. Mary J.

This may not be perfect – and in fact she looks like she’s just stopping by after her sister’s wedding – but she’s selling the SHIT out of that look and whatever else you may think of it, is neither inappropriate to the Derby, nor is it remotely dull.

[Photo Credit: Getty]

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    • allyc

      Marry J looks awesome. That’s how you do it.

      Also, I have it on good authority Ginnifer Goodwin was a complete and total bitch this weekend. Lots of eye rolling and snide comments. Clearly she’s above the Derby.

      • kikisayshi

         That makes me sad because I am a big fan of GG and I think she always looks so sweet. Maybe she was just pissed that someone made her wear that outfit.

      • http://www.youtube.com/user/toodleskitty79?feature=guide AWS

         GG always looks like she has the Wicked Witch of the West’s broomstick stuck up her ass.  She needs to get OVER herself right now!

    • http://twitter.com/thedogsmother thedogsmother

      The tattoos. The perfect touch…

      • http://pulse.yahoo.com/_UXHOYXPNJJ4MQH6IHYSI3G5ILI M

        I feel like they should have been more covered.  MJB’s dress looks a little “Joyce Leslie” to me also.

    • http://theargiehome.blogspot.com/ Gus Casals

      Can’t believe how unflattering Debra’s dress is, she sure as
      hell doesn’t have that body shape, and if she did, she would be dressing it in
      a completely different way.

      Ginnifer (and many of the other hat wearers) should not have
      her hat so deep into her head. Was it too windy and they were afraid they would
      blow away?

      • Spicytomato1

        I know, Debra’s dress is the epitome of boxy. It’s like she’s wearing a modified refrigerator box.

      • funkypeanut

        I wonder whether this is just a general lack of experience with hats. Very few people wear them often anymore, so when they do, they just follow their first impulse and cram them down on their heads.

        • golden_valley

          I suspect she has a small head and fine, slippery hair.  Plus she still has that pixie cut.  There’s not much for the hat to grip onto. I have similar head and hair.  Hats always slide down until they come to rest on top of my ears.  That’s probably what’s happening with her.

    • JaneDC

      I truly believe that the women who know how to do the Derby are the southern women who’ve been seeing and doing it all their lives. Everyone else just doesn’t get it.

      • http://joyouslifesf.wordpress.com Kiltdntiltd

         True facts, Jane.  Its an event the rest of the nation just doesn’t really comprehend, in its social context.

        • JaneDC

          Exactly. I think it’s really a women’s occasion. You get to dress like a deb, have your hair blown by the wind just so, sip on juleps and delicately scream for your favorite horse. What could be better?

          • http://joyouslifesf.wordpress.com Kiltdntiltd

             Why, having your horse win, against all odds, of course.  lol

        • JaneDC

          Exactly. I think it’s really a women’s occasion. You get to dress like a deb, have your hair blown by the wind just so, sip on juleps and delicately scream for your favorite horse. What could be better?

      • kikisayshi

         This is true. I am not a native, but I do live in Kentucky and I know that you pick the hat, and then get the rest of the outfit to match.

    • http://twitter.com/Lily1129 Lily

      Work it, Mary J. 

      Ginny’s dress isn’t hideous, but that hat might be the least flattering hat I’ve ever seen.

      • Spicytomato1

        I know, that hat. She looks like she should be enjoying the early bird special in Boca after an afternoon of bridge.

    • http://joyouslifesf.wordpress.com Kiltdntiltd

      You GO, MARY J!  Show them other ladystars how its done.  Its perfect for the Derby. Its got the southern vibe, a touch of glam, and its matchy as hell.

    • kikisayshi

      Mary J always knows how to bring it! 

    • funkypeanut

      I read somewhere that DM was contractually obligated to wear that hat and make sure that it was the focus. It’s advertising Grey Goose vodka, so I imagine that she had to wear grey, too. You’re completely right about the belt, but I think that the pearls were a poor choice, too, because nothing says “church lady” like white pearls.

      Oh, Ginny, did they not tell you that there would be cameras?

      • http://twitter.com/GaraStJames Gara St. James

        Yes, Debra was specifically doing a tie-in for the Grey Goose Greyhound cocktail advertising, so her entire outfit was probably pre-ordained. But it definitely could have been tailored better.

    • BazoDee

      Kate’s stylist seems to have it figured out. I don’t think it is that hard. Of course she is a size 000 and that makes a stylists job easier -but these are dreadful. Look across the pond for help on this one!! 

    • Laurie Bergman

      I know it’s the sponsor backdrop, but all I can focus on is Debra Messing exclaiming “Yum!” via thought bubble. That is some unfortunate photo positioning. Oh…and I love Mary J’s rose-and-net confection.

    • butterflysunita

      Mary J. Blige looks all kinds of fabulous.  I like Debra Messing’s dress, but I agree that the look overall isn’t flattering.  Ginnifer Goodwin looks awful.  

    • Scarlet39

      All three looks are unfortunate, but GG’s really looks like she half-assed it. 

    • TieDye64

      Mary J., how I love ya! Ginnifer, you’re just too sad for me on a Monday morning.

    • HomeOfficeGirl

      Sorry, not loving Mary J in this red get up for the Derby.  She can look amazing and very classy.  But this… it’s just so red and tatt’ed up.  It’s screaming “Williams sisters” and that hardly ever comes across as classy.

      • Caaro3

        She looks fabulous and sexy.  I LOVE her hat.  

      • http://vhanna26.typepad.com Vera

        While I love MJB’s hat, and she’s selling the look, everything else looks tacky. Really needed to cover that shoulder tat as well.

    • mmgk

      I totally disagree on Mary J.  I think she usually looks pretty fab, but this is so tacky.  I just can’t with the shiny red gloves and matching Minnie Mouse heels, especially. 

    • mmgk

      I totally disagree on Mary J.  I think she usually looks pretty fab, but this is so tacky.  I just can’t with the shiny red gloves and matching Minnie Mouse heels, especially. 

    • CassandraMortmain

      I was at a Derby party this weekend and every woman there looked better than this sad bunch.  The hats were better, too.  Actually, Debra looks appropriate but just too boring.  And Mary J looks kind of fab but the red satin gloves and all the tats sort of ruin the look.  And are those red suede shoes?  (shudder)  Ginnifer, on the other hand, is just a ridiculous mess on every level.  She’s a walking illustration of what not to do.  She rarely gets it right on the red carpet but this has got to be one of her worst attempts ever.

    • CassandraMortmain

      I was at a Derby party this weekend and every woman there looked better than this sad bunch.  The hats were better, too.  Actually, Debra looks appropriate but just too boring.  And Mary J looks kind of fab but the red satin gloves and all the tats sort of ruin the look.  And are those red suede shoes?  (shudder)  Ginnifer, on the other hand, is just a ridiculous mess on every level.  She’s a walking illustration of what not to do.  She rarely gets it right on the red carpet but this has got to be one of her worst attempts ever.

    • http://www.beautifymylifeblog.com Jessica

      Other than the hat, I actually love Ginnifer’s whole look.

    • http://www.beautifymylifeblog.com Jessica

      Other than the hat, I actually love Ginnifer’s whole look.

      • http://pulse.yahoo.com/_2P2ANLRZ6YAVGONA36I2AQJYGI VicD

        I don’t mind the hat – imagine finding the exact shade of tomato red as the dress!  But those espadrilles!  UGH

    • http://twitter.com/algaechick algaechick

      In the full length shots…no “Yum” anywhere in GG’s picture. DM gets one, right above her hat. Mary J gets a row of shouty “Yums!”. 
      Coincidence? I think not.

    • MilaXX

      MJB for the win! I”m not loving the gloves, but I dig the hat and dress on her.  I
      like Messing’s look, but since she’s been back in the public eye, it
      appears that she is having trouble dressing her 40 something figure. Her
      footwear is often odd and the fit on most of the things she has worn is typically off. I miss the glam she bought to the RC during her Will & Grace days. Then we have Ginnefer. This time I like the dress, but the hat & shoe just make me sad.

      • http://profiles.google.com/grandiva1968 e jerry powell

         For some reason, I get the impression that Messing was somehow aiming for “Understated Matron” and missed it by that much.

    • Snailstsichr

      I think Debra would have looked a lot better in different shoes. A grey and white spectator pump? Or would that be too matchy-matchy?

      • formerlyAnon

         I have a weakness for spectator pumps, so I feel that they would be a perfect addition!

    • http://pulse.yahoo.com/_EDI2DLE7DE3YPW2ONIHBWOVHMA ecallaw

      Geez, I really need to throw in the towel.  I actually liked what Ginnifer Goodwin was wearing.

      • Alisa Rivera

        Me too! I love the dress, the hat and shoes don’t bother me. Not sure why people hate it so much.

    • Little_Olive

      All messes. No. 

      Outfits aside, I have problems with the concept: I really don’t appreciate that they turn this into another red carpet, as they did with Comic-Con, Coachella and a long etcetera. Is there any event devoid of celebs now? If they want to, can they go and not make a pint about it as if they had aaaalways loved it and known everything about it and followed it?  
      There is a sartorial backfire to such celebrity invasion, which is that the event starts to lose its uniqueness and the fact that the dress code has a history; it ceases to be natural. In other words, I don’t think we can give Kim K a pass for being there just because she is wearing a hat. 

      There. I vented my monday morning. Looking forward to Ascot now.  

      • Lina_bee

         I have to disagree. Celebs have been doing the Derby for decades upon decades. I do take your point re Comic-Con — I remember when actual comics creators were the stars there, not the movie tie-in people — but KD has a very, very long history of attracting famous faces.

        • http://frankbettecenter.org/ sleah_in_norcal

          agreed.  celebs are among those who have always had the money to do the derby up right.  wish i had the bucks to go. 

      • http://vhanna26.typepad.com Vera

        For the celebs, life seems to be one long RC after another.

    • SpcilK

      Aunt Mary is killing me. She looks like she just left the set of a Tyler Perry movie.

      • http://profiles.google.com/grandiva1968 e jerry powell

         You take that back!
        Tyler Perry is THE DEVIL!

      • http://vhanna26.typepad.com Vera

        Oh Wow! That’s precisely it.

        • HomeOfficeGirl

          Yep.

    • newleaf1

      Mary J’s hat is completely KILLA.  

    • http://pulse.yahoo.com/_2P2ANLRZ6YAVGONA36I2AQJYGI VicD

      Miss Blige is KILLING IT

    • Lina_bee

      Oh, Ginny, you look like an elementary school art teacher in your mother-in-law’s old sunhat. Who did this to you?

    • marilyn

      Debra’s dress makes her look thick through the middle.  The color is flat and uninteresting.  Ginnifer’s outfit looks like she got it at K-Mart to wear to the beach.  Mary looks sharp, but you’re right-she looks like she just came from a wedding.  

    • http://phantomminuet.blogspot.com/ MinAgain

      I actually like Ginny’s look better than Debra’s.  The hat is nice, but that gray dress does nothing for her.

    • PeaceBang

      YES! It’s MARY J. BLIGE on the left and it’s MARY J. BLIGE ON THE RIGHT… what a winner Derby look, LOVE it. Miz Goodwin’s head looks way too tiny under that big, dumb ugly hat and her ears look silly and now I have to look down at my shoes because I’m so embarrassed for her.

    • minnye

      Oh Mary J. Blige… you know how to look classy, for sure… but yikes woman. I hear Jerry Stiller yelling HOOCHIE MAMA!

    • minnye

      Oh Mary J. Blige… you know how to look classy, for sure… but yikes woman. I hear Jerry Stiller yelling HOOCHIE MAMA!

    • BigWhiteGrannyPanties

      I am troubled by the word “YUM” in the balloon above their heads.  Ginnifer Goodwin looks like her dog just died or something.  

    • formerlyAnon

      Madonna may not be able to bring gloves back into the mainstream, but I’m thinking that Ms. Mary J might be able to!

    • http://vhanna26.typepad.com Vera

      Ginnifer looks beat, and that dress looks like it’s sporting the Univision logo. DM’s dress makes her look thick, and, as a previous commenter sagely pointed out, Mary J. looks like she just stepped off a Tyler Perry movie set.

    • http://twitter.com/LOfficielEbony TheVeryLivingEND

      It cost MJB a lot of money to look that tacky.
      I love Ginnifer’s dress.  The rest? Yuck! Those espadrilles? Who’s decision was that? Somebody’s getting fired.
      And, Debra’s look just makes me tired.

    • http://www.facebook.com/profile.php?id=768540908 Badriya Al-Badi’a

      Mary J was also there to sing “My Old Kentucky Home,” as is tradition right before the Derby, so what she wore also had to serve as stage wear to some extent–no doubt that dress was clearly visible on the bandstand from across the track :-)