In or Out: Olivia Wilde in Oscar de la Renta

Posted on October 07, 2011

We almost shouted “WERQ!” on this one, but bit our tongues after the scrolldown.

Olivia Wilde in Oscar de la RentaOlivia Wilde attends the Tod’s launching party of Tod’s Signature Collection at the Italian Embassy in Paris, France in a vintage Oscar de la Renta gown.

Olivia Wilde in Oscar de la Renta

Olivia Wilde in Oscar de la Renta

Olivia Wilde in Oscar de la Renta

First, the good: It’s an incredibly striking dress and she can pull it off when a lot of mere mortals would have problems making the attempt. Her hair and makeup are very soft and pretty, which suits her and which was also a good idea because the dress is so focus-pulling. But kittens. Those shoes. Now we realize just hours ago we shouted “WERQ!” at someone else even though we didn’t like her shoes, but this goes beyond mere dislike. Those things are HIDEOUS. Worse, they manage to do something we would have thought impossible: they pull the eye away from the dress. That is absolutely the wrong thing to be doing. Focus-pulling shoes go with simple dresses; you don’t pair them with a focus-pulling dress because then it all becomes way too much.

Are we wrong here? We’re asking.


Vote Now!

IN! You’re wrong here!

OUT! T Lo, how can you ask such a thing? You’re NEVER wrong!

Voting on Emma Stone’s Cruella de Vil look is still wide open, darlings. Make your opinions known.

[Photo: Getty]

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  • Anonymous

    Oh my, I thought they were flats in the first pic. IN; 80% of the look works, especially if you crop the pic so you don’t see the shoes.

    • Anonymous

      I thought they were flats too!  But them not being flats make them no less ugly and wrong for this dress.

    • Anonymous

       In, but only because the rest of it works. The shoes. Yeah, not so much.

  • IN, though I hate her for being so beautiful 

  • I have to say – I hate that dress.  It looks like a souvenir plastic doily from some shop in Madrid that caters to elderly English tourists.  It’s stiff, it makes her ass look big, and the closeup of the ruffled hem shows that it’s sewn to the dress badly, with big lumps. 

    • Anonymous

      I thought, on a second look, that it wasn’t terribly figure flattering, as you said. NO WAY should girlfriend look thick.

  • Anonymous

    Oh honey, no.


  • Anonymous

    There’s something very wrong here, but I’m not sure what it is. Something about the dress is off, or it needs someone more statuesque, or something.  And the shoes, oy.

    • Anonymous

      I agree. I wonder if the bottom portion of the dress is making it look wonky. Or maybe it does need to be worn by someone taller. Hmmm.

      • I think it’s a skosh too long for her and it’s swallowing her waist. A belt maybe?

    • Anonymous

      I agree.  Can’t put my finger on it.  TLo likes the hair, but I think that is part of the problem – too flat against her head?  looks greasy?  Maybe it is her posing, leaning back?  OR maybe this dress was just made for a shorter person?  It’s just an awkward neither here nor there length?  

      And those shoes are hiddy.  I also thought they were flat sadals in the first picture, and then they look that way in the last, too.  I think the dress just flat out needs to be longer.  It’s so overwhleming, it needs to go all the way.  

    • Anonymous

      Maybe also that the curvy pattern in the torso of the dress fights against the natural curves of the body and looks disorienting. I almost looks to me like it should be a fun beach cover-up with little sandels and a straw bag.  Then it would be fun and interesting.  For a cocktail type thing it should have ended before the ruffle – then it might look chic.

    • She looks like a Spanish grandmother at 5:15 Saturday Mass. 

      • Anonymous

        That’s it!

  • I forgive her. In.

  • Out. I hate the black bag, too. And I think the dress is wearing her. She just doesn’t have the presence to stand up to it.

  • Anonymous

    Wait a sec – the ONLY thing you don’t like here is the shoes? This fabric was on my grandmother’s dining table. It looks garish and heavy and the design makes her look 20 pounds heavier. And then the shoes. K-mart. Oh-livia. Big time OUT. 

    • Yes!  Exactly.  I don’t understand how these women who are teeny-tiny can leave looking like they’re attempting to sneak a pygmy elephant out of the house.

      It also makes her look really short. 

      Personally, I think the shoes are the least of the problems here.

  • Grace Ritt

    It’s not the shoes exactly, I think the bottom of the dress is a little…iffy. I don’t know. Better shoes might have made the dress look better. I don’t know, I still think it looks like a rug. OUT. 

  • Anonymous

    I want to like the dress, but it is all a bit too much. Then I got to the shoes. Whoo boy, those are really awful with the dress. They might be awful on their own, too, but I can”t really tell.

    And can I just add? You two are serious blogging bitches today! I am impressed!

  • Anonymous

    OUT, I hate it all

  • Those shoes look like the $25 shoes they sell in Mandee for the preteen set. I do think the dress is very striking, but perhaps a bit odd for her coloring? I can’t quite put my finger on it, but I’m not fond of that orangey-red on her.  She’s so gorgeous, she can do way better than this!  Out, i’m sad to say.

  • John Manson

    She’s “IN” despite the shoes (I can totally understand them keeping her away from WERQ thought). She needed shoes that were as minimal as possible and certainly not black. 

  • narita_rayna

    IN!  but i hate those shoes so much with that dress.  accessories should have been anything but black.  i would have even settled for silly putty.

  • Vaniljekjeks

    Not a WERQ, but still an In.  That’s a tough dress to pull off and she’s doing it.  I just hate the shoes.  It could be worse, they could be silly putty. 

  • Wrenaria

    Not bad from the knees up. But not good enough to be in IMO. OUT.

  • Anonymous

    No, of course you guys are never wrong. I just don’t know what shoes would go with this dress, now that I’m thinking about it. Perhaps that second round at happy hour is warping my judgement.

  • Anonymous

    In: If the dress were a tunic and the shoes were hidden by pants.


  • Anonymous

    OUT…ruins the look

  • … I see the problem here. It’s a perfect RC dress because it grabs the eye. But it’s failing in the “Wow!” factor except for “Wow! No, sweetie.” She can pull off the colors but the pattern was a bad idea. OUT

  • Anonymous

    Well, this is the saddest OUT I’ve ever given. That dress is stunning and she’s stunning in it – but the shoes. The SHOES! Seriously? What idiot thought those shoes were a good idea!? Someone needs a good smack upside the head for this fashion nightmare. Jeez. Now I’m all grumpy.

  • You’re not wrong. OUT, out damn shoe!

  • Anonymous

    OUT!  I like the idea of the dress, but it erases her figure, the hemline is baffling, and the shoes make me want to take out my eyes.

  • Sara__B

    Those shoes ruined everything. Those shoes are so horrible that I thought I didn’t like the dress. But the dress is okay, for lace. She’s  making 3/4 sleeved neck-to-ankle, red and white lace work, and I wouldn’t have thought it possible. But those shoes! They may be the ugliest black heels in the history of the world. You’re right, T Lo. Out.

  • Anonymous

    I’m gonna say a kinda sorta IN, and that’s only because the dress is spectacular. The shoes are too busy for it. But I still think she looks great. 

  • Anonymous

    I’m an IN. Well, maybe an in. I like that she’s doing something new. The shoes don’t bother me too much — I’m just grooving on her whole look.

  • Anonymous

    It’s all downhill once you get below the hips. Sorry girl but OUT. Shoes are hiddy and I thought they were flats at first.

  • Anonymous

    Wow, you guys are on fire today! So many posts! Thank you!

  • If this ended at the knee, I think I would love it even with those hideous shoes. I like the top half of the dress that much. But the hemline is horrific and the shoes are awful. OUT.

  • I’d have to say “Out.” I don’t like the shoes, either, but that dress length and that fluffy, scalloped, sorta-mermaid-but-not-quite-bottom, are not working for me more.

  • Anonymous

    For two in a row, I’m going to have to remain neutral.  I love the dress IF it stopped at the V–not having all the doilies at the bottom.  And those shoes need a simpler dress. 

    Borderline Don’t Cry for Me Argentina with it all together.  Or an extra in The Three Amigos.

  • You are not wrong. Those shoes are HIDEOUS and they look crazy uncomfortable on top of it.  They totally ruin the look. OUT.

  • Anonymous

    I think that hemline is pretty dire, in addition to the unfortunate shoes; OUT.

  • Anonymous

    Something about the shoes makes the outfit costumey, like she needs a mantilla and a rose in her teeth. 

  • I LOVE her ring, though. 

  • Lauren Frankel

    IN, the dress is just so gorgeous regardless of the shoes.

  • Those shoes are horrid. The dress is great but on her it looks dowdy. I think it would look better on someone maybe taller or just more.. I don’t know, curvy or outrageous? OUT

  • R. L.

    Out.  I’ve seen better looking flip-flops at Target.  The dress looks like one of those vinyl picnic tablecloths.

  • Anonymous


  • So sad.  OUT.  The shoes completely ruin it, you’re right.

  • the shoes are cute but not w/ that dress. i still give her an in. i like the dress and her.

  • Anonymous

    Egads!!!  Those shoes!  Ruin the whole look!  I don’t think there is an outfit they WOULD go with!  Other than that, I love the dress, and she looks gorgeous!  

    So, what shoe would be right???  

    oops… forgot to officially vote…OUT..cuz of the shoes!

  • Anonymous

    IN IN IN FOREVER IN. I don’t know what the fuck you guys are talking about with the shoes, I think the shoes and the bag make the look much more interesting.

  • i’m just trying to figure out what vintage it is. 80s? it’s the only one that makes sense, on first glance. on second glance, no decade makes sense. 90s? three years ago? i am really curious.

    i must be the only person here who is not crazy about the dress. but as soon as something reminds me of, i dont know, the wang chung dynasty, i give up on it immediately.

  • Anonymous

    Sigh, an out.  I had this same exact problem with a wedding I went to this summer – I wore a ruffled salmon colored dress with a black grosgrain ribbon that lined the front.   Sounds grotesque, but it was a pretty dress and very, very difficult to find shoes for – I am still cringing about my choice.  Enough about me, though – let’s talk the dress.  My guess is that Oscar De La Renta originally designed this dress for some sort of poolside or beach party where the rich beyatch who commissioned it didn’t have to wear shoes in the first place. 

  • Anonymous

    Oy! Simple black pumps! Simple black pumps! Out!

  • what the fuck is on the tops of them? are they patent leather hats or something…shit…she would have gotten an IN but those shoes! OUT!

  • Anonymous

    In.  The shoes have a spanish flair to them, maybe a bit costumey, but I still think she looks awesome.

  • Anonymous

    Hot tablecloth mess, OUT!

  • in

  • In the first shot they actually have the appearance of orthopedic sandals. I was relieved to see in the profile shot they were not, but what in God’s name is wrong with those shoes?  They don’t immediately look ugly.  They’re a sassy black sandal with a flower.  Worse things have been worn.  But god they’re like kryptonite to fashion in this outfit.  They make the dress look too long or too short.  They’re shiny.  They should not be shiny.  Instead of making her look like a devastating “I’m a divorced princess, bitches” hottie, she looks like she broke a heel on the way over and had to stop at Payless for an emergency pair. 

  • Anonymous

    After performing several complicated scientific calculations (no, not really) it was found the shoe hideosity ratio was not inversely proportional to the face, hair and dress fabulosity. So, an In, even though those shoes caused my feet to instantly blister up at the mere thought of wearing them.

  • It’s not just the shoes. The whole hemline of the dress is just wrong. If it were cut off straight around knee-length with a little interest at the hem, I could take it. As it is, it looks like it should be disguising toilet paper in a Russian grandmother’s bathroom. No, Out, just Out.

  • Shorten the dress to tea length, and get rid of the HIDEOUS plastic shoes.  The flouncy hem…eh, if done well it could have been cool.  OUT.

  • Out. Dress too long, don’t like the ruffled hem, and the shoes are freaking WRONG. However, her hair and make up are lovely.

  • Anonymous

    If a flamico dancer used her grandmother’s tablecloth to make a dress this would be it.  And I don’t understand the shoes at all.  What are those things?  Melted plastic flowers?  I can’t tell.  Anyway, it’s all an out for me.  Out, Out, OUT!

  • Anonymous

    I bought that dress from a street vendor in Cozumel in 1992. Out!

  • Anonymous

    NO NO NO.   The dress looks like Spanish Table Cloth and all she needs in a mantilla in her hair.  Make it a black one to go with those hiddy shoes.  You are right TLo, the shoes make my eyes sink to the floor.  I’d rather her in a different hem on the dress, with (god forbid) some nude shoes than this .. this..  OH MY EYES!

    • Anonymous

      This means OUT, btw.

  • Anonymous

    Out. The shoes kill it. 

    TLo, did you formally retire “If We Were Her Gays”? I miss it, and had been looking forward to the challenging curvy-lady portion of that program. Just, if the minion opinion is solicited. 

  • MilaXX

    OUT that shoe completely ruins the look for me because it make me hate the bottom of the dress and I think with the right shoe I would love it.

  • Sobaika Mirza

    IN. I think she looks stunning, even if the shoes are fug.

  • Anonymous

    IN.  Despite the horrid shoes. The dress, hair, and make up look fantastic. She got more right than wrong, but a better (simpler) pair of shoes would have pushed this into WERQ territory.

  • Anonymous

    OUT. You’re absolutely correct. The shoes are seriously cray cray and ruin the whole look.

  • Nora Mulllin

    If ever there were a time for nude shoes. . .

  • Anonymous

    Oh god, those shoes.  Who gave her those shoes?  S/he should be shot.

    Edited to add: T Lo, it’s true, you are never wrong: well, okay, almost never but in this case you are soooo right. OUT.

  • Elena

    Out.There is just such a major disconnect going on here. I can’t forgive these shoes.

  • Joyce VG

    Beautiful woman, beautiful dress and ugly shoes *whimper*.  OUT. 

  • Anonymous

    All you have to do is cover the shoes with your hand and see how great she could have looked. Whoever is responsible for this should be in big trouble.

  • IN. I’m voting an automatic in for anyone NOT wearing platform pumps. No, I don’t like the shoes, but that dress is beyond fabulous and  I love the big ring on her finger.

  • You are so right. Completely, dead on right. What an amazing dress and she looks so pretty but the minute I saw the shoes I was like, ‘whaaaa?’ They look like foot tumors.  So distracting and so disappointing because wow! that dress!

  • Ruth Gottesman

    Will there be flamenco dancing later? OUT.

  • I hate the hem of the dress. If it were a traditional hem, or if it were a mini, then it would have been amazing. OUT, which is a shame, because it could of been breathtaking. There’s too many bad things going wrong below the knees for me to give this an ‘in’.

  • Anonymous

    OUT. Love the dress, but the shoes are terrible with it. I also don’t like her hair, it’s too casual and “running errands” for the look. But it goes with the shoes, so maybe the (poor IMO) plan was to be all couture in the middle and strolling-the-embarcadero at both ends.

  • Anonymous

    From the knees up, she looks fantastic, so I’ll give her an IN. 

    I’m just not looking lower on these pics again…shudders

  • Anonymous

    IN on the aggregate!!!

  • Anonymous

    OUT. Those shoes are horrendous!! And I don’t love the bottom of the dress–but the shoes are just awful!!!!

  • Anonymous

    I think her hair and makeup are terrific, but I’m not a fan of anything else. OUT

  • Out.  I thought they were flats in the first shot… schlubby, house shoe style flats.  It kills the whole dress.

  • Anonymous

    Her hair is soft and pretty? No way! It looks like she pulled it back in a quick ponytail to do laundry.

  • Anonymous

    OH, THE SHOES. WHY. No, T&Lo, you are NOT wrong. OUT.

  • I agree with you, but I really like the dress on her. In.

  • Roz

    She’s IN only if you change the definition of IN. Please don’t do that. OUT.

  • Anonymous

    For the love of god, OUT! At first glance, the shoes looked almost like flats from the front–there was so much height on the flower that it shortened the look of the shoe. Which in turn made it look to me like a flat almost frumpy finish to an elegant dress. A shame, because I like that dress more than her usual fare.

    Not to mention that they suck your attention like hideous black holes.

  • Anonymous

    IN-N-OUT! Fabulous vintage dress. But you are not wrong. Those shoes are awful; they look like they are adorned with flattened dog poo.

  • Jacquelina La Bomba

    Iiiiiiiiiiiiiiiiiin her defense, the shoes don’t look half as bad from the side. And no offense to the fabulous Mr. Renta, but that little vestidito should’ve ended at the knee. And dropped the silly fishtail hem. Sorry, pretty lady, but you’re OUT.

  • Anonymous

    I think the shoes are awful, but the dress is even more hideous and her hair looks terrible.  There’s a woman behind her with black ankle socks.  What kind of shitful event is this anyway?

  • Anonymous

    You are so right, TLo.  Out.

  • Anonymous

    You are so right, TLo.  Out.

  • Lisa

    Oh, no no no no…. no WERQ, no!

  • Anonymous

    Boy, I wish we could grade on a scale, cuz she’s fab from the calves up.  The awkward hem length accentuates the hiddy shoes.  OUT

  • Anonymous

    Out. I tried to imagine anyone else getting away with wearing those shoes. Nope. The only person that comes close is Divine. If Barbara Stanwyck wore those, Fred McMurray would have pushed her off the train.

    I want to like the dress, but it swallows her. If the neckline were lower or the ruffles gone, it might work. Higher, darker, hair and more dramatic makeup (and a long, long neck) might balance the look.

    • Anonymous

      OK The Barbara Stanwyck comment made my entire morning.  I don’t know you but I adore you.  xoxo

  • Anonymous

    You are not wrong.  Those shoes are bad!  But I love the dress and everything else so much I want to just forget them.  IN 

  • Anonymous

    Looking good, looking great, looking… OH HOLY MOTHER OF HELL THAT IS UGLY.


  • Those shoes turn the whole outfit into a flamenco dancer costume. Love you, girl, but you’re OUT.

  • So out.  Because…yes…those *shoes*.

  • Anonymous

    OUT….just barely. Love the dress, but those shoes…

  • Sharon Mvundura

    As I read the opening commentary I though oh TLo, let’s not exaggerate. But then….I scrolled down and my eyes bled. OUT OUT OUT OUT

  • Jen McElroy

    Oh ew. I loved the dress! Although not too sure how I feel about the bottom design. Perhaps that is just the shoes ruining everything within the immediate vicinity?

  • BuffaloBarbara

    Out.  I don’t even give her points for the top.  She looks like a waitress in a flamenco-themed restaurant.

  • Anonymous

    Out.  I love everything from the ankles up. And I wouldn’t have thought it was possible for shoes to steal attention from that dress, but here we are…

  • OUT. The shoes ruin it.

  • Anonymous

    Maybe the dress in black works, but the red and white reminds me of a toilet paper doily.

  • Nicole Merrill

    The shoes are awful, but I love the rest of the look. IN!

  • In.  I agree with you but still think the dress is so awesome that it overcomes it.  But seriously, what was she thinking with those shoes?

  • Robert Wilson

    I’m not that much of a ‘fancy’ gay guy and was surprised by how much I enjoy reading what T&L think about fashion. Most of the time I can see what they mean in their critiques and werqs, and I have a profound respect for the way they are able to focus in on the specific reasons a ‘look’ failed or succeeded. But, if even I can tell that the shoes were a terrible choice and make what would have been a great picture seem awkward and off-putting, then yeah, the shoes suck, and she should punish her stylist.

  • Jessica O’Connell

    Oh…OUT. Those really are awful shoes. Also, I honestly wish the dress was shorter and the skirt less full, but nonetheless, without the shoes this would have been an in. What a shame.

  • What shoes DO you wear with a dress like that? D:

  • Grandma’s doilies. OUT.

  • I am dead serious you guys, I NEED that dress for underneath my Christmas tree this year.  LOVE!  The shoes look like they were stepped on during a tango before the photos were taken.  OUT!

  • Anonymous

    It’s so pretty! IN. 

  • Anonymous

    With all the ugly, ill-fitting, questionable footwear these people wear to red carpet-y events, I’m surprised the minions are going nuts over THIS pair of shoes.  Let’s not be so rule bound, huh?  The dress is fantastico!   IN

  • Anonymous

    I hate all of it. OUT!

  • I hate everything below her knees. 

  • This would be an amazing dress if it were a tube and stopped somewhere around the knee – top, middle, or bottom doesn’t matter. As it is, it looks like a prairie dress for a confused pioneer woman. And those shoes should never be seen or spoken of again. Don’t like the bag either. OUT

  • totally right; that’s a GORGEOUS dress, but it’s also a whole lot of dress. plus, they look like a little girls dress-up heels…

  • OUT. The needle scratched the record for me where the skirt starts to flare out. EUCK. This would’ve looked better as a fierce mini or above-the-knee at the LONGEST, and any shoes other than those scary things she’s currently wearing. It’s too much.

  • No, you’re not wrong, T Lo. Such a pitty for that dress. OUT.

  • It’s weird, but I think the effect changes when she crosses her legs. When they’re not crossed, the shoes make sense to me with the dress and give it almost a flamenco feel (except with the huge ass flower on the foot instead of in the hair). When she crosses her feet, the balance of the look goes wonky and makes me scratch my head. With that being said, I think the look is an overall IN.

  • Anonymous

    OUT. I don’t think she is pulling off this dress. It looks stiff. You guys are absolutely right about the shoes. The hair is good. I like the make-up. The softer eyes are a HUGE improvement.

  • Anonymous

    The shoes DO ruin it. Out.

  • Anonymous

    You’re wrong, but only because the dress is also not great. A little too Grandma’s tablecloth for me, and both the three-quarter sleeves and the lower skirt are a little too flamenco costume.  Ole. 

  • In, just because the dress is so stunning and everything from the shoes up looks beautiful. If the shoes had simple straps instead of thos fug flower-like things on it, it might have worked. 

    (The only thing I don’t like about the dress is that it makes her quite boxy, she doesn’t really have a waist in the thing…)

  • Out! I’m sure you been wrong once or twice, but this is not it! I’m also not sure if I think that the dress would have been way better if it stopped right above the knee and had a more simple silhouette to balance out the print, or if it’s just the shoes again.

  • Pick one, the shoes or the dress, but not both – it’s too much. OUT.

  • Anonymous

    OUT – it’s one of those “illusions of curves” dresses, which somehow manages to make her look like a rectangle. Also, that ruffle? The scrolldown had two levels of disappointment, and while I agree that the shoes pushed it too far, that ruffle is where it started to go wrong.

    Great colours, hair and makeup, but not the right dress and definitely not the right shoes (when would they ever be right?).

  • Anonymous

    Out, she only needed half the dress and new shoes.

  • Aren’t those the same Roger Vivier shoes Tilda Swinton wore a few months back, except in a different colour?

  • Anonymous

    Those are actively offense shoes.  Why?  WHY?  Everything above the ankles is so lovely!  I can’t get past them though — they really do ruin the outfit.  A very sad OUT.

  • Apathy Incarnate

    Out. Big, big OUT!

  • Anonymous

    Out!  The Shoes are awful.

  • OMG, you’re absolutely right.  Before I even read the commentary, my eyes went right to those 1950s plastic POS.  It is a pretty dress and WHY on earth would you wear black shoes with that dress!  This is a dress that needs the nude color shoes TLO hates so much.

    This is an OUT!  And it’s too bad, because I dislike OW, but here she really would’ve looked pretty…. if she had cut off her feet!

  • Anonymous

    When I was in Bruges, I bought a beautiful lace doily.  And they put it in a very pretty paper bag – that looked EXACTLY like the print of this dress.  It looked better on the bag.  OUT – but she is so very very pretty. I won’t even comment on the plastic shoes.

  • Anonymous

    out.  you are absolutely right, those shoes are so ugly and distracting, they ruin the rest of the look.

  • Anonymous

    the shoes are prom cute — obviously not the choice for THIS dress.  the ideal shoes for this dress would be something close to invisible. amazing dress. 

  • Yeah, wow… terrible shoes.   I didn’t love this dress…but she does look great in it – it’s interesting.

  • Susan Foster

    Out.  The pattern is right on the borderline between interesting/ugly, but what tips to out is the fact that it looks just a smidge too large.  It loses her figure.

  • Anonymous

    The shoes don’t bother me at all… just imagining how she will manage them in the gravel behind her!!  

  • out,  would have worked better cut at the knee.  Shoes…. OUT!

  • the bottom 25% of that dress is HIDDY!!

  • Anonymous

    No, no, no.  Everything is off here.

    And what’s with the “scripts” error since you changed websites?  Really is tedious to read your fabulous blog now and was hoping it would have taken care of itself, but nope.  Any way to fix this so it doesn’t stop everything from loading until the error is cleared?

  • Thank God for the ugly shoes. At least they take the focus OFF that ugly dress!

  • Anonymous

    Oh dear.  I just gave in to the fact that I now need Official Old Lady Shoes (too many years of gorgeous, but badly made and badly fitted shoes), and even I wouldn’t have tried on these shoes, much less paid for them and then wear them in public.  Who’s styling her?

    • Anonymous

      I hear you. I have rheumatoid arthritis and can’t always wear the fabulous shoes I’d love to. So, I looked at these shoes and thought, “Well, hmmm…if I saw these in a ‘comfort shoe’ store would I try them on?” The answer, “Oh, hell NO!” But I did think for a fleeting moment, maybe they’d be cute on their own. But no.

  • Anonymous

    The length of the hem and the sleeves is atrocious as well.  Those 3/4 bell sleeves give her fat wrists-something I’m fairly certain she doesn’t have. 

  • Anonymous

    yeah, she looks like a flamenco dancer.

    that’s an out.

  • Anonymous

    I agree with everything you say.  And the shoes are bad enough to push the look to OUT.

  • Anonymous

    After seeing that dress I was sure there was going to be a Carol Burnett a la Scarlet O’Hara reference: “I saw it in the window and I just had to have it”.  Seriously, the expanse of that window treatment is just too much.

  • Anonymous

    The pattern reminds me of the pattern on the iconic Givenchy dress that Audrey Hepburn wore in “Sabrina.” It worked on that dress because it was used sparingly and for effect. This is too over the top for me. Besides, we had friends with wallpaper like this (back in the 60’s). I am not even going to talk about those shoes (I think she raided my garbage can in the 80’s or something). Sadly, OUT.

  • Anonymous

    The shoes literally looks like turd.

  • Those shoes give me hives. Out, of course. 

  • I always look at all the pictures before I read anything, and when I saw those awful shoes, I laughed.  Out loud.  Seriously, they’re that bad.  So it isn’t you.  Those shoes are ridiculous.  The dress should’ve stopped above the knee and there is something strange about the sleeves.  I want very bad for this to be an in because the dress is such an almost werq, but she just didn’t cross the finish line.  Out.  With no reservations but a lot of regret.

  • Anonymous

    Well, the accessorizing definitely isn’t perfect. The shoes are, indeed, hideous. But the rest of it is gorgeous and I love the dress, so I’ll give the rest of it a pass. I’ll have to go with an IN!

  • I really hate the hem– she can ALMOST make it work for me, but the shoes are utterly atrocious and the entire ensemble just looks silly. and kind of ugly. So…. OUT.

  • Mary McClelland

    out. yikes what an unfortunate combo. What an unfortunate look!

  • Mary McClelland

    Also, what makes the matronly shoes even worse is the bare nails – like they were complete afterthought because she forgot her real shoes. It just looks so haphazard, the hair, the hem. All of it, but the shoes especially so. 

  • Anonymous

    Shoes are the worse thing, but I have to say, I don’t like that dust ruffle along the bottom either. I like the PATTERN of the dust ruffle and think that is a lovely way to hem the dress, but keep it straight and not flared out.

  • The dress looks like a plastic tablecloth

  • AWFUL shoes.  Awful.  

  • Scroll-down fug to be sure.  A shame.  BEAUTIFUL dress. what. a. shame. out. 

  • Anonymous

    Out. Because T Lo is never wrong. 

  • I liked it up until her ankles became visible. I think if the dress had a few more inches and less focus pulling shoes it would be a no brainer in. As it stands, it’s an OUT!

  • Jesus, Mary, and Oprah! When I saw the thumbnail I thought why the hell isn’t this a WERQ? But then I clicked…… OUT!!!!

  • Erin Nice

    Out. Good lord. Those shoes hurt my feelings. And my eyes. 

  • This reminds me of a bedspread I had as a child, back in the 70s.  The bedroom also had red shag carpet, don’t even ask about the wallpaper.  I still have nightmares about it.  Therefore, I must give this look an OUT.

  • BerlinerNYC

    Why can’t that dress just end earlier? It’s like the over-long album version of a song that really just needs to be enjoyed as a 3-minute radio edit…  I’m much more disturbed by the superfluous final portion of the dress than by the shoes…

  • Anonymous

    So dead on. They look like slippers that might, say –  match her beaded bead jacket.  The dress needs to be flipped. So the hem pattern is near that beautiful face………..i’d call this one –  oddly attractive.

  • Anonymous

    Don’t much like the dress but I think if ever there was a time for putty shoes, this is it!

  • Anonymous

    100% OUT.  Nothing can excuse those shoes.

  • Anonymous

    OUT: from the thighs up it’s great, but I hate the bottom of the dress and the shoes kind of make my eyes twitch.

  • Anonymous

    You are very very right.  OUT!

  • Anonymous

    Odd and Out.

  • The shoes up the flamenco factor (can that be Bravo’s next PR-clone? “The Flamenco Factor”!) which may have been what the stylist intended, but if so, that just shows that stylists do go wrong sometimes. Of course TLo aren’t wrong – and yet this look still earns an IN.

  • Anonymous

    Out. Exactly what you say with the shoes. The dress is a big French toile de jouy sort of print that belongs on an upholstered chair.

    I thought it should get a slight pass because it’s vintage Oscar de la Renta, but I’m still not sure who could rock that dress and what shoes ought to be worn with it. But it’s so very red and so very white and those unflattering three-quarter length sleeves and neckline. I don’t know why I’m trying to talk myself into liking (tolerating) it just because it’s vintage. It’s a dress you can spot clear across the room, but one that all the women are talking about in the restroom. ‘Did you see what Olivia is wearing? WTH?’

  • Anonymous

    OUT …love the hair and makeup and nothing else. That dress puts pounds on her.

  • It could be me, but I do not like that dress.  Maybe if it didn’t have that oddly ugly skirt/dust ruffle/bottom-piece-of-hideous-undeserving-of-the-Oscar-de-la-Renta-name THING, it’s wouldn’t evoke such a visceral reaction of dislike in me, but even then, I’d only upgrade to “don’t hate it” status.

    The shoes are atrocious, of course.  My niece owns a strikingly similar pair that she looks adorable in.  Of course, she’s 2 yrs old and could look cute wearing just a diaper. That it appears on a grown woman in a photo-op situation is bizarre.

  • Anonymous

    Where on earth did she find those horible shoes? OUT!

  • Anonymous

    That dress looks like the tacky flocked wallpaper that my insane Aunt Carmela put up in her living room which was full of fake “antiqued” Louis de Something furniture…  TOTAL out!

  • I don’t like everything that’s going on below the knee. Shitty shoes or no, that is one awkward hem length. That fabric looks very, very stiff and heavy. Amputate the dress at the lower thigh or knee and we’ll talk.  OUT.

  • Anonymous

    Hiddy… OUT!!!!!!

  • The shoes are out.  I think perhaps something in white and red that is flamboyant but blends with the dress might be in order– a bootie or ankle boot with some cray cray flamenco design on them….  Matchy matchy is needed for this dress.  A white sandle with bright red toenail polish…

  • Anonymous

    she’s always SOOOO close!!!! uch! out

  • Anonymous

    Not lovin’ the look.

    The dress looks like flocked wallpaper a friend’s parents had in their living room in high school – accessorized with gold furniture. All that was missing was was the “Marlon Brando” or “Frank Sinatra” painting on velvet to complete the look.

    So I have to say – NOT A WERQ.

  • Anonymous

    The dress looks like Transylvanian needlework — great in an table runner but hiddy on a dress. I hate the neckline, her hair needs more volume and … the shoes are so ugly I can’t even find the words. OUT.

  • It’s such a badass dress that I can forgive the schoolteacher shoes (I say that as a schoolteacher who would wear those shoes but with a pair of jeans and a cute top, not a red carpet dress!) IN

  • In.  But you’re not wrong about the shoes.

  • elzatelzabelz

    OUT- she RUINED a vintage Oscar gown. Travesty.

  • I’m actually more concerned about the bottom of this dress than the shoes.

  • Anonymous

    The dress looks too ornate and heavy. I think it would look better sleeveless, or perhaps with a lower neckline.

  • Now I am The Bee

    Yikes  Bad dress and worse shoes.  But–are they from Tod’s, since she was at a Tod’s event?  Even so–not good.  OUT.

  • Anonymous

    have to OUT the dress… I could live with the print but length and the scalloped hem aren’t doing it for me!!

  • Ouuut!! The length, the shoes and the matchy clutch are all too much..

  • lilibetp

    You sure the caption shouldn’t say “Oscar de la Renta dress wearing Olivia Wilde?”

    I always wondered what happened to my Aunt Helen’s old plastic red and white tablecloth.  Now I know.

  • Oh dear me. That dress just is not flattering, she has no discernible shape in that picnic blanket. And the shoes are not good. Why would you try to busy up a look that’s already so ADHD?

    Eh, she gets an IN because she’s working that shit, even if I’m not a fan.

  • Anonymous


    She’s a walking Rococo table with lace topper.

  • Anonymous

    ICK! Why is she wearing a tablecloth? The shoes are terrible, but not worse than that dress. Oh so very OUT.

  • Anonymous

    Fail.  That hem is awful.

  • Ehn. I would dearly love to pass this but those shoes look like they were made with trashbags, and the length of the dress is just ugly. Out, with tears. 

  • Where are her castanets?

  • Anonymous

    OUT. Mostly because of the neckline.

  • Anonymous

    The shoes are awful and I’m not a huge fan of the length of the dress either. Love the rest of the look but what’s going on below the knees is enough for an OUT. Sadly.

  • Anonymous

    Out.  The shoes need to die.  The dress is gorgeous (though I’m not sure about the flowy hem), but as soon as I saw the shoes, it was all I could see.  I was staring at them in horror.

  • OUT
    I wish that the dress didn’t have doilies on the bottom and the shoes are horrible!

  • M Carlson

    Yes, you’re wrong. From the side, they look fabulous although I will concede that from the front they are not so good. To me, they seem to tie in a flamenco vibe with the dress.

  • OUT!  Those shoes look like bedroom slippers, and they make the dress look like a housedress.

  • Anonymous

    Yeah, she really managed to ruin a great look. I don’t even think the shoes are bad; it’s just that they are SO wrong for this dress.

  • Anonymous

    I saw the outfit and instantly thought “Italy.” Seems she saw “Italian Embassy” and thought she needed to dress the part. Ugly ugly ugly shoes.

  • Anonymous

    Out.  Cheap Chinese restaurant place mat meets Spanish tablecloth meets tiny toe cowboy hats.

  • oohsparkley!

    Out.  That dress should be shortened to knee-length or above and different shoes.  I’m not sure what shoes would work with the dress as is.  I can get how some dresses with bad shoes would still be an in, but these shoes ruin the whole look.

  • Chantelle James

    OUT. The dress is gorgeous, as are her hair and makeup but those shoes ruin the entire look.

  • Jessica Kyler

    The shoes, at first glance, looked like a pair of payless flat sandals that stay on the shelves for years because no one buys them. I wish the dress was a bit longer. I think the length of the dress is what makes it difficult for us to even ignore the shoes for a moment. If the dress were longer, it wouldn’t look like a baroque-printed frame for her feet. I certainly think black was a poor choice for the shoes, as well as the bag.

    I think she’s right to opt for a thin sandal. Perhaps a strappy, very subtly designed metallic gold stiletto would have worked. I’m not really sure. I’d say nude, but I’m not even sure that would work. hm.

    She took a chance, but that’s a dress that needed some research beforehand.


  • too much going on down there at the bottom. OUT.

  • aimee_parrott

    OUT.  I actually think the dress is lovely, but it’s either too long or too short for her.  And the shoes are hiddy.

  • Anonymous

    A reluctant IN. Gorgeous dress, AWFUL shoes!