Jason Sudeikis and Olivia Wilde at the Drinking Buddies Premiere

Posted on August 16, 2013

We had every intention of praising these two for perfectly executing a sort of NYC boho-glitterati look, but the longer we look at the pictures, the less we buy it.


Jason Sudeikis and Olivia Wilde attend the premiere of “Drinking Buddies” in Los Angeles. Olivia Wilde is wearing Olivia is wearing a vintage t-shirt paired with a Robert Rodriguez skirt, a Smythson clutch, Jimmy Choo pumps, and a Cresta Bledsoe cuff.

A little bit too perfectly executed, if you know what we mean. It’s one of those things where we can’t quite articulate why we feel this way, but the whole thing feels contrived as hell, with every element, from his shoelaces to her t-shirt, having been meticulously curated and chosen. Obviously we don’t fault them for using stylists, even for casual events like this, but the outfits need to have that stylish-but-thrown-together feel to them and these just don’t.

We want to like it for the slight chic/cazh vibe they’re both putting off, but if we stare at it too long, they both look like they’re wearing costumes of a sort.


[Photo Credit: Andrew Evans/PRPhotos.com]

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  • joancarol

    He needs a new hair-do. His forehead is getting too wide. He looks like a tulip.

    • GorgeousThings

      He’s looking more and more like his Mitt Romney impression.

    • Kristy Sheldon

      This is the worst I have seen either of them look. Love is blind.

  • YoungSally

    He gets an 8 for being less obviously “styled”…she more like a 5….the t-shirt isn’t right….if anything it needs to be knotted at the waist or hanging over a pair of pants…..this looks too much like Travolta in the Santa Cruz Slugs T-shirt from Pulp Fiction.

    • Heather

      Hey! I’m a proud Slug! 🙂

  • Donyelle

    Hipsters’s Date Night

  • birdie & bijou

    I was okay until I hit the GIANT WHITE TENNIS SHOES. But I think they are adorable together and seem like genuinely nice, normal-ish people. Also, love the eye makeup.

    • Kristin McNamara

      *basketball shoes. (Mentioned below.. I’m fairly certain those shoes are Jordans.)

      • Constant Reader

        I’m pretty sure that in certain parts of the country, “tennis shoes” means any athletic shoes, not just shoes worn specifically for tennis. Tennis shoes = sneakers, doesn’t matter what style.

        • Kristin McNamara

          Ohhhh. Whoops! Didn’t realize that.

          • Constant Reader


        • Darren Nesbitt

          Where I’m from everything that’s an athletic shoe is called a tennis shoe lol

          • MoHub

            And from when I’m from as well.

        • Mod_girl

          Or, as my mother used to call them, “tennies”

      • Brad Watson

        I got a basketball shoes jones, oh baby, oo-ooo-ooooooooo…

    • Heather

      Is he wearing lifts? Is he short? I think she is regular height, 5’6″ or 5’7″ ish.

      • mlle

        They look to me like they’re just sneakers with a fairly thick sole, but I have no idea whether he’s short or not.

  • Girl_With_a_Pearl

    I usually like her outfits, but this one’s kind of a yawn. Also, too much eyeliner.

  • I wonder if they had to disrobe somewhere to return it all afterwards or if they were able to send it back via courier the next day?

  • hughman

    “I had deodorant stains on my t-shirt before it was cool.”

  • Dylgeah

    At what point does a T-shirt go from “old t-shirt at the bottom of the drawer” to vintage? Is there a hard and fast rule? 7 years? 10? Just curious.

    • Rhonda Shore

      That’s not really a cool vintage t-shirt…an old clash t-shirt or something late 70s, or even an earlier Springsteen album would have been better.

      • Adrianna Grężak

        What are you talking about? The River was released in 1980!

        • Rhonda Shore

          It’s not cool vintage for that time…it was a mainstream album.

    • AmeliaEve

      Is it even true vintage? I actually saw that tour live and I don’t remember the concert shirts looking like that. I have a feeling it’s mock vintage, licensed to Old Navy or something to recycle the images from the album cover.

      And it would make a lot more sense to me with funkier skirt, either something long and swirly or, actually, this would be the time to pull out the black leather.

      • Adrianna Grężak

        I think it is mock vintage. I have a couple of Bruce Springsteen tour tshirts, and they are not soft and luxurious as hers!

        • AmeliaEve

          I got a bee in my bonnet about this and did some searching around for Springsteen T’s. Most of the hits I got for The River turned up this photo. I feel quite sure at this point that it’s mock vintage.

          Also, looking at some other shots of her I see that this skirt doesn’t merely have angled hem – it spirals all the way down to her ankle in back. It’s hard to see the whole shape with the black backdrop. Even worse than I thought.

  • Eric Stott

    They both look slightly bombed.

  • bethlael

    Glamming up a band tee with a pencil skirt, pumps, and some kick-ass jewelry is one my favorite looks. Everything about both of their ensembles works except for his hideous Bieber shoes.

  • NDC_IPCentral

    Too much makeup on her for a t-shirt and alleged casual air. And for the loveofoprah, why can’t these star-types cadge shoes that FIT?

    His shoes – Florida retiree clompers.

    • Kristin McNamara

      Retiree? I’m pretty sure those are Jordan hightops. That’s more like hip-hop garb, not hip-replacement garb.

  • newleaf1

    A vintage t-shirt with an Ann Taylor looking skirt and black pumps? No.

  • TSkot

    He couldn’t be more adorable.

  • Sara

    I think she looks great, but I do love her. She seems really smart and BS-free.

    He, however, looks ridiculous.

  • GorgeousThings

    Yeah, but you can’t fault her for the tee shirt. That’s fabulous!

    • Lori

      I don’t know about T&Lo, but I definitely don’t fault her for the tee shirt. I fault her for what she’s wearing with it and how try hard the whole thing looks.

  • Little_Olive

    That’s… not an outfit, really. It’s clothes thrown together.
    Minus the jacket, he is dressed like a 10 year old. I particularly hate those pants.

    Also, and this is going to sound really weird, his face is like one of the Thundercats who had some herbal refreshment in the limo.

  • CNM

    I like her outfit and her makeup is gorgeous. But I hate his look. I think that maybe it’d work if he lost the jacket, but I’m also no fan of the denim shirt.

  • d4divine

    His jacket is wrong….the t-shirt wouldn’t look so bad if she were wearing skinny jeans…the list goes on an on…so wrong and not very much right.

    • Constant Reader

      I was thinking the same thing: her outfit looks like something a receptionist might wear on casual Friday and then go directly from work to meet her friends for happy hour — and even that hypothetical person would be trying for “hipster” and missing it.

  • Sue_Asponte

    Wow, I didn’t know Jason Sudeikis could even do douche. Yet there is he, looking like the epitome of douche. My impression of him as the eternal “nice guy” is shattered forever.

    • largishbearishAtlish

      I tend to like Jason, but something about the pic…he really looks like he is phoning it in…hard. Its too ‘cute’ (or is that bland?)

  • alyce1213

    I think he’s very funny, talented and pretty nice looking, and I can’t believe I’m going to say this — his overdimpled grin annoys the shit out of me.

  • formerlyAnon

    I don’t get hers, but since I have no exposure to NYC boho-glitterati, I am not surprised.
    His look would be perfect with different shoes (suede or leather), though not, perhaps, in line with the genre.

  • kimmeister

    What is up with that black strip of fabric hanging down just one side of her skirt? That would drive me batty.

  • olsonam

    The blog “Celebrity Gossip, Academic Style” has a new post about Olivia Wilde and I think I can now tell Wilde apart from Olivia Munn. PS, the post is NSFW.

    • housefulofboys

      Ha! I thought I must be the only one who kept getting the 2 Olivias mixed up!

      • veleri

        nope. you are not alone.
        and thank you!

  • DominoEstella


  • surfergirl70

    I think she looks pretty great, contrived or not, and quite honestly, with that face, she can wear whatever the hell she wants. Gorgeous.

  • Laurie Landry

    He: looks like he’s been binge drinking.

    Her: I haven’t worn a t-shirt tucked-in since the 80’s. But then again that was when the Bruce was popular.

  • NoveltyRocker

    Yeah… maybe that’s why Jason Sudeikis confounds me, he does tend to look contrived. They both have given off vibes like they prefer to be casual but when everything is brand new and sparkly clean and just-so, it just doesn’t look inspired. I think casual, thrown-together looks get their power from being picked out on one’s own. And I freakin’ don’t get if Sudeikis is setting out to be a rakish cool-guy, alpha type but he looks like Ed Helms and is known as a sketch comedian so my brain get’s confused by his posturing and film choices. Ever since his movie about the well-to-do friends who all have an orgy in the Hamptons, I don’t get “him.”

  • elemspbee

    he looks like a dork. She looks good.

  • Kate

    his sneakers are much to clean for “NYC boho-glitterati”

  • marlie

    Is it weird that I just can’t buy them as a couple? And this rather artfully contrived photo-op doesn’t help.

  • Miss wks

    Doosh Shoos

  • Orange Girl

    Oddly, I think these two might be kind of normal-ish people who actually like each other, and that’s why they look so awkward posing together. She looks somewhat comfortable, but he’s holding on for dear life.

  • largishbearishAtlish

    am I the only one that is being bugged by the glowing raccoon/cat eyes? far away its not so bad, from the up close pics looks like she used ALL the make up samples..ugh.

  • LauraAgain

    Hey! I have that Springsteen shirt!

    (Too much eye makeup on Ms. Wilde).

  • Anniebet

    Okay, I give up. She wins. A Bruce tee shirt? I’m now officially in love with her, or at least her shirt.

  • MilaXX

    If she was wearing skinny jeans and a more basic clutch or bag, it would look less styled.

  • conniemd

    He always looks like a douche to me, kinda smirky. She, OTOH, is one of the more interesting looking actresses. Loved her is 13. She isn’t the standard bland blonde and has an interesting face and gorgeous eyes, though, as someone else mentioned, too much eye makeup here.

  • fauxprah

    his hair is more ‘did’ than hers.

  • procrastinatrice

    I think she looks fantastic and carefree. I don’t find her ensemble contrived. He just looks annoying with his stupid shoes.

  • SewingSiren

    I don’t like concert T-shirts tucked in with business skirts.
    And I don’t know what he’s playing at. Did he just get off the swing shift at the steel mill?

  • Warrior89

    First of all, he is really cute. Their outfits are dumb though. Real dumb.

  • jjfg

    Faux concert tee tucked into a fitted skirt? 13 is making my eyes twitch. Never mind I hate Springsteen. He might have made it if he’d worn some old Chucks. The glaringly new white tires kill it.

  • I like looking at couples when they deflect attention to the other. Like she might be thinking “Look at him! He’s wonderful! Can you believe he’s with me?!” But when I see shots like these I think she’s thinking “Look at me! I’m with him! Aren’t I wonderful!” It annoys. And repugs.

  • Rand Ortega

    He looks like that kid who got EXACTLY what he wanted for Christmas.

  • CatherineRhodes

    Trying too hard.

  • nicewilliams

    Does her skirt have some strange long fabric piece hanging from the side? (see bottom picture) #eyetwitch

  • Addicted2Glamour

    This just SCREAMS ‘trying too hard.’

  • lac87

    I honestly don’t think they were styled for this. If you ever see pap shots of them, this is pretty close to their street styles (minus her bottom half). And those Jordans are meant to be kept spotless, even if they maybe weren’t the best choice for this outfit.

  • KC

    I give them a pass because a friend of mine was able to spend time with them and says they are some of the coolest, most humble and laid back people ever.

  • Aurumgirl

    That’s a hunk of fabric behind her left leg–how ugly. And he’s wearing shoes for children. These are the kinds of clothes you don’t want anyone to see you wearing.

  • MoHub

    That’s some eye makeup she has on there. And is she wearing something? And is someone with her? Sorry, but I can’t take my gaze off the raccoon eyes.

  • Ruth Preston

    What’s the female equivalent of douchey? Because, that.

  • acevedob

    NO. Just no.

  • jen

    Spot on, you guys. His shoes and her t-shirt pushed their outfits from chic/cazh to super lame and trying too hard to seem like they’re not trying too hard.

  • KikiAvocado

    I never realized how much she looks like Giada DiLaurentis. I agree his hair needs to deflate a bit

  • Cassidy Olsen

    It looks like they’re trying to be Diane Kruger and Joshua Jackson and failing. Only Josh Jackson would never wear that terrible of an outfit.