They say that no one can get everything. Some people are really good looking, some people are highly intelligent, some people are very artistic, and some people are born with an enormously philanthropic heart. But almost nobody gets all of those things, or large amounts of them, anyway. That’s why you have to wonder if Olivia Wilde is one of us mortals, and if so, how in the world did she manage to pull off having all of those in spades?
Olivia Wilde, who was born Olivia Jane Cockburn, but uses the last name “Wilde” in homage to Irish author Oscar Wilde, is an accomplished actress, producer, director, political and social activist, and socialite. While most people know her for her work in the television show House, M.D., or her various roles in a myriad of films, Wilde has produced films on the devastation and aftermath in Haiti, mobilized young voters in support for the Democratic Presidential nominee Barack Obama in 2008, and actively worked with Gucci’s “Chime for Change” campaign, which aims to raise awareness and funds of women’s issues in terms of education, health, and justice. Oh, yeah; there’s also the fact that she’s insanely beautiful, too.
In fact, for better or for worse, we actually do have photographic evidence that Wilde isn’t completely perfect. As you’ll see below, for all the looks that she’s had over the years that have blown us away in general, she’s had her fair share of public appearances where she looked far from her best. To that end, we decided to compile a list of 10 times that Wilde absolutely blew us away, and 10 times when her outfits were on the opposite end of that spectrum.
20. Blew Us Away: Red And Gold
In one sparkly maroon mermaid dress worn on the red carpet of the 73rd Golden Globe Awards in 2015, Olivia Wilde showed off why her looks are basically flawless. The full-body, form-fitting dress hugs tight to her well-maintained physique, without one iota of being over-the-top. The sequins bring the dress a level of “bling,” transforming it into something that’s befitting of a major Hollywood event. The deep-plunging neckline brings out the strong, alluring, feminine vibe that Wilde absolutely radiates, and the red and gold choker necklace just takes a very high-class look even higher.
Wilde got dolled up for the event, as she and John Krasinski presented the award for “Best Television Series – Drama.” The award was given to Mr. Robot on USA Network, which beat out wildly popular series’ like HBO’s Game of Thrones and Netflix’s Narcos.
19. Just Plain Bad: The Gloves Just Make It Worse
Look, Olivia Wilde can make a lot of clothes look amazing, because she simply looks amazing herself. That being said, what on Earth is this thing? This dress looks like a shower curtain from a seven-year old girl’s bathroom, in which the little girl wanted everything to be an obnoxiously loud shade of pink. Wilde wore this “dress,” if you can call it that, at the “China Through The Looking Glass” Costume Institute Gala in 2015. This definitely fits much more closer to “costume” as opposed to “couture.” And the absurd gloves she wore make this look even more of an eye sore. We have no idea why people were raving over this look that she tried to pull off, because this might be one of her tackiest looks to date. Luckily, she still looks beautiful, but that isn’t surprising.
18. Blew Us Away: Her Plus One At The Oscars
At the 86th Annual Academy Awards in March of 2014, if you took a look at Wilde from the neck up, there’s absolutely no way anyone would’ve ever guessed she was seven months pregnant (other than radiating a motherly glow, perhaps). But Wilde came to the Oscars with future son Otis Alexander Sudeikis safely inside of her baby bump, with the mom-to-be draping both of them in a high-collared, black and white Valentino gown, paired with Lorraine Schwartz diamond chandelier earrings.
Prior to the event, Wilde poked fun at herself on social media, tweeting a photo of the beer-bellied Homer Simpson, captioned, “Pic from Oscar fitting.” Something tells us that no man would ever confuse Wilde with Simpson, regardless of the size of the former’s belly at the time.
17. Just Plain Bad: With Apologies To The Cheetah
Walking the red carpet for the premiere of film The Five-Year Engagement during the 2012 Tribeca Film Festival, Wilde wore a Yigal Azrouel animal-print dress. The dress looks literally like she just found cheetah skin and had Azrouel turn it into a dress, which is rather ironic considering Wilde considers herself a vegetarian, and was voted the S*xiest Vegetarian Celebrity of 2010 by People for the Ethical Treatment of Animals (PETA).
Here’s what’s even more ironic: Wilde is currently in the midst of a real-life five year engagement to fiancé Jason Sudeikis. Sudeikis proposed to Wilde in January of 2013, and while the couple has two children together – son Otis Alexander Sudeikis and daughter Daisy Josephine Sudeikis – they still haven’t tied the knot themselves.
16. Blew Us Away: The Change-Up
In the critically panned film The Change-Up, which encompassed the clichéd “body switching” plot line among two best friends (played by Jason Bateman and Ryan Reynolds), Wilde played the role of Sabrina McKay, Bateman’s alluring legal assistant whom he ends up going on a date with, since he’s now inside of Reynolds’ body.
As McKay (Wilde) arrives for the date, the camera slows down on her as she enters the restaurant and heads to the table, and we have to say a huge “thank you” to the producers for doing that. The way she looks in that red dress would bring any man on this planet to his knees. Her character is basically the embodiment of what every guy dreams of in a woman: the type of girl who can be a perfect lady, or one of the guys, and is equally stunning doing so.
15. Just Plain Bad: Rolled Out Of Bed
We’ve all had those days. You know, the days where we had to go somewhere that we really weren’t interested in going to, so you throw on some comfortable clothes, run a comb or brush through your hair, and maybe put on a decent pair of shoes over an outfit that’s more comfortable and functional than presentable, and then be on your way.
That’s our guess as to what happened with Olivia Wilde in this photo, because there really isn’t any other explanation of note for the way she looks. She has on a bunch of casual cardigan-style tops on top of a white undershirt, and leggings and boots underneath.
This looks more like something you’d put on for a casual Friday night when you’re heading to your friend’s house, when the two of you have no plans other than to finish a bottle of wine between yourselves.
14. Blew Us Away: Sparkling At The Golden Globes
There’s no other way to put it: this entire look makes Olivia Wilde every lady’s “girl crush” (or just incredibly envious), and every man’s head turn.
At the 68th Annual Golden Globe Awards back in 2011, the ridiculously poofy skirt and even more sparkly dress somehow made this certified smoke-show even more stunning. In this picture, she’s basically about as close to a “perfect 10” as you’re going to get in real life.
Alongside Robert Pattinson, Wilde co-presented the award for Best Foreign Language Film (won by Danish film In a Better World). In her personal life, she was only weeks away from announcing that she and former husband Tao Ruspoli were separating after just under eight years of marriage (Wilde first got married when she was only 19 years old).
13. Just Plain Bad: The Christmas Ornament
In January of 2014, at the 71st Golden Globe Awards, Wilde was about six months pregnant with her future son Otis Alexander Sudeikis. We have zero disagreement with the fashion magazines raving about Wilde looking as motherly as ever, at least from the neck up.
From the neck down, while the dress did a fantastic job of showing off her flawless figure combined with the baby bump, the green mermaid dress just seemed off. To us, she just looks like she draped herself in really fancy Christmas wrapping paper, or tried to dress herself up like a Christmas tree ornament. In this emerald-beaded Gucci dress, Wilde resembles more of an “overdressed for a holiday party” look, as opposed to the glamorous and cool look her stylists were going for.
12. Blew Us Away: Combining Sheer And Lace
You know you’re insanely beautiful when you can make a somewhat questionable dress look absolutely perfect. That’s what Wilde accomplished in this Monique Lhuillier dress that she wore when appearing on The Late Show with Stephen Colbert in June of 2017.
Most critics agree that the dress would’ve hardly garnered a second look from shoppers who just saw it on a hanger in the store, but when Wilde donned it, it looked like a stylishly versatile dress you could wear for a fun night on the town, or on a late-night talkshow appearance. Wilde made an appearance on the late night comedian’s show to discuss her first foray into Broadway, in a rendition of George Orwell’s classic novel 1984.
11. Just Plain Bad: Turning A Photo Into A Dress
At the Hollywood Foreign Press Association’s 2013 Installation Luncheon at the Beverly Hilton Hotel, people went absolutely “Wild about Wilde” (terrible pun intended) when she wore this Clover Canyon dress.
Personally, we must be missing something, because this dress looks like something straight out of a street market. Some of the designs and patterns are neat, but the majority of them just look like your basic patterns that you’d find on a poncho somewhere, and the building in the background which is depicted in black and white looks like some gaudy building that some European colonialist built to honor themselves for coming to someone else’s land and assuming control of it. None of that comes to mind when you’re thinking of high fashion. We’ll give a hard pass when it comes to this look.
10. Blew Us Away: Turning Heads At The Emmy’s
Very shortly after making her debut on Fox’ hit television show House, M.D., and before she became an A-list Hollywood actress, Olivia Wilde started turning heads when she wore a long silver chiffon evening dress with beaded cap sleeves, gently ruched bodice, and an elegant floor length skirt, at the 60th Primetime Emmy Awards in 2008.
Most fans of the show will remember Wilde for her work as Dr. Remy “Thirteen” Hadley, who worked on Dr. House’s (played by English actor Hugh Laurie) diagnostics team after a gruelling, Survivor-like selection process. Hadley’s complex and secretive character made her an intriguing addition to the show, especially after her story began to unfold throughout the series; namely, the fact that she was bi and diagnosed with Huntington’s disease, which threatened to significantly shorten her life expectancy.
9. Just Plain Bad: Mix And Match Fail
The first thing we thought when we saw this outfit was “bumblebee on the top, peacock on the bottom.” Apparently, the outfit was supposed to be a summer-inspired way to mix and match separate printed items of clothing, as opposed to the National Geographic inspired motif that immediately struck us.
But the wine and yellow striped cap-sleeve sweater plus printed ruffly handkerchief skirt just seemed like too much at one time. It’s like when you buy two great items from the store because they’re great summer pieces, and then decide you want to wear them both at the same time. The blue shoes and blue belt might tie together with the skirt, but the sweater just sticks out like a sore thumb when placed on top of it all.
8. Blew Us Away: Dark Green Cut-Out Dress
The pop culture blogosphere anointed Olivia Wilde a “hot mom in the city” after seeing her rock this open-stomach, forest green Rosie Assoulin dress at the 2016 CFDA Fashion Awards in New York City.
The mother of one was pregnant with her and Jason Sudeikis’ second child (daughter Daisy Josephine Sudeikis), and was very open about the fact that she still felt very alluring, despite being very pregnant, and wanted to flaunt her womanly curves by wearing something that was both fashionable and effortless. Wilde commented that when she saw Assoulin’s dress, she thought the dress of befitting of someone she herself would want to be, so she was honored to wear that dress and be that type of woman for the night. To us, that’s the perfect type of beauty: strong and confident, without trying too hard.
7. Just Plain Bad: The Farmer In The Dell
Most men will never understand how much women crave the basic concept of “comfortable clothes” when they’re pregnant. Considering moms-to-be are carrying a living, breathing being (along with a whole bunch of other related fluids and tissue), they deserve a pass for choosing comfort over “camera-ready.”
In this photo, Wilde looks plenty camera-ready from the neck-up, with the perfectly straight and flowing hair, the classy choker around her neck, and the stylish sunglasses. But from the neck down? Well, that’s a different story. With the overalls and rolled up jeans, she looks more like someone straight out of America’s heartland, versus a resident of Tinseltown. Wilde looks like she’s on her way to go work in a rice paddy, after buying herself a to-go lunch.
6. Blew Us Away: The White Queen
If you happened to be a single guy on the red carpet of the 2009 Emmy Awards, and saw a woman as superhumanly-beautiful as Olivia Wilde looked, you’d probably think you needed to have the confidence of George Clooney, the looks of Ryan Gosling, the body of Dwayne Johnson, and maybe the money of Warren Buffet to stand a chance with a woman like her.
In this white Marchesa gown, Wilde looks regal, if not divine. Fashion critics commented that the beige fabric connecting the white parts of the dress (including the back) usually doesn’t work well on most people, but given that Wilde has the looks and the figure that most runway models would absolutely love to have, she makes the dress look absolutely impeccable.
5. Just Plain Bad: The French Pantomime
We’ll start by stating the obvious: if looks could kill, then the expression on Wilde’s face in this photo would put her away behind bars for the rest of her life. Of course, the black-and-white shirt she’s wearing in this photo looks like one of those old school prison uniforms, which kind of ties things all together in this photo, we suppose.
For as dazzlingly good looking as she is in this photo, the outfit doesn’t do her the slightest bit of justice. In complete honesty, if someone told us this photo was taken for a Halloween photo shoot, and she was dressed up as a French pantomime, we probably would have believed you. That’s probably not the look that Wilde, or the photographers, were going for in this photo, however.
4. Blew Us Away: Bold Yet Classy
Wilde was the talk of the 88th Academy Awards in 2016 when she wore a white, Grecian-style pleated ivory gown from Valentino’s Haute Couture 2016 collection. While she accentuated the outfit with a glittery choker and a pearl-encrusted clutch purse, it was that deep plunging design which everyone noticed.
The dress in general was the perfect “yin and yang” balance to what makes Wilde so alluring: her classic beauty combined with a subtle yet obvious sensuality. She was accompanied by fiancé Jason Sudeikis, but even he recognized that he was the second fiddle among the couple that night. Later in the evening, Wilde joined comedian Sacha Baron Cohen as Presenters of the films Room and Brooklyn on the Best Picture segment.
3. Just Plain Bad: The Wannabe Suit
Ladies, please don’t try and borrow this look from Wilde, and think you could wear something like this to a job interview (plunging neckline notwithstanding).
For as beautiful as Wilde is, she just looks like a frumpy rock star who was forced to put on a suit and dug something out from the back of the closet, in terms of this look. If we had to caption this photo, it would be, “They made me put on a suit, but I’m really here to party.” Standing next to Kate Mara, who’s wearing a simple but elegant dress, makes Wilde look even worse. This might be one of our least favorite looks out of all the bad ones on this page. Congratulations, we suppose, to that suit, for finally being an outfit that can make Wilde not look good.
2. Blew Us Away: The Meadowland Premier
Leave it to a bombshell like Olivia Wilde to make even a pantsuit look ridiculously stunning. Then again, she did receive a big assist from renowned designer Michael Kors, as the pantsuit was one of his designs.
The look was described as an homage to the 1970s with a contemporary twist, which you can clearly see with the deep-plunging neckline that shows off her almost unfairly toned midsection. The lower part of the jumper was floor-length, giving Wilde the perfect combination of sophistication and allure.
Wilde donned this outfit at the New York screening of the film Meadowland, in which she was one of the lead characters. The event was hosted by legendary director Martin Scorsese, and Wilde called it one of the proudest moments of her professional life.
1. Just Plain Bad: That’s Just A Bathrobe
Olivia Wilde looks like she’s borrowing one of those looks from runway models, in which their face is saying, “I haven’t eaten in two weeks, and i’m incredibly hangry (hungry and angry).”
As far as the outfit she’s wearing, we’re not sure if this is supposed to be a toned-down kimono, or a bathrobe that’s been turned into “fashion” by putting a silky black scarf around the waist. We’re going with the latter. Tell us that you haven’t seen something like this (sans the scarf) at a fancy boutique hotel. Given the distressed look of her hair, you’d have little reason to think she didn’t just step out of the shower, or the bedroom, about 15 minutes ago. Why anyone would consider this a fashionable look is beyond us.
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