Looks from the 2020 Oscars I won't soon forget - for better or worse

Screen Shot 2020-02-10 at 4.55.00 PM.png

This year’s 2020 Oscars definitely piqued my interest in more ways than one. All three of my favorite movies of 2019 walked away with at least one award, Best Picture was awarded to a non-English language foreign film for the first time ever, and the lack of a host made for some cringe-inducing introductions and award presentations. So the red carpet ended up being one of the last things I thought about. But I still think there’s a lot to talk about in that many looks have been quite polarizing. The Best and Worst Dressed lists across all publications can’t seem to come to a consensus of what looked good. So I decided to throw my hat into the ring and talk about what I thought of this year’s looks. My favorite look just might surprise you this time around.

 

Charlize Theron

For Better

Once again, Charlize Theron keeps it classy in Dior Haute Couture. Not much risk-taking here, but its simplicity pays off. Especially paired with her natural makeup look and ultra-neat hairdo. I’d have probably swapped the necklace for earrings and the shoes for something more sleek and dramatic, but all-together, it’s classic Charlize.

Charlize Theron in Dior Haute Couture and Tiffany & Co. jewelry.jpg
 

  Brie Larson

For Better

You all know I’m not the biggest fan of Brie Larson. I find her smug and condescending, and can’t sit through a minute of her cringeworthy interviews. But I am willing to put my distaste for her aside for a moment to compliment this look. This sparkling number is classy yet sexy, making it perfect for the Oscars. And the choice of hairdo and accessories are perfectly subtle enough to not detract from the gown. The shoes are a little small and giving me cliff-hanger toes but besides that, this is great.

Brie Larson in Celine and Bulgari jewelry .jpg
 

Florence Pugh

For WORSE

This dress makes me sad because it had so much potential. Its color and sheen looks wonderful on her, her makeup is fantastic, and the neckline is flattering. But this is at the end of the day, a ruffled catastrophe. This dress could have worked if there was more volume or less. More ruffles, or fewer. It unfortunately fell into this awkward in-between that made it seem half-finished or not thoroughly thought out. There’s just way too much going on at the bottom of the dress for it to make sense as a high-low number. Not to mention those shoes remind me of an early 2000s prom. It’s too crazy to look subtle or classy, but not exciting enough to be avant-garde. I have a strong feeling we’ll be seeing a lot more of Pugh in the future, so she has plenty of time to establish her red carpet style.

Florence Pugh in Louis Vuitton.jpg
 

Penelope Cruz

For Better

When she stepped onto the stage that evening, her gown took my breath away. Her figure looked incredible and the shape of the skirt is exactly what I wear in my daydreams. I just would have plucked that white flower and string of pearls off this. They felt like after-thought embellishments rather than part of the look. They reminded me of when I played dress-up as a child, pinning floral hair clips to my dress necklines and wrapping necklaces around my waist. Had it not been for those details, this could have been my favorite look of the night.

Penélope Cruz in Chanel and Swarovski jewelry .jpg
 

Sigourney Weaver

For Worse

While she herself looked great that night, Sigourney Weaver’s dress distracted me on the red carpet and on stage as she introduced the medley of the Best Original Score nominees. While the color was lovely, the boat neckline mixed with the scrunched sleeve, rope belt and pleated skirt just made for a lumpy twisted mess that didn’t do justice to her its Grecian inspiration or Weaver’s beauty.

Sigourney Weaver in Dior Haute Couture .jpg
 

 Hildur Gudnadottir

For Worse

Again we’ve got another case of a woman who looks beautiful and has a great figure, wearing a dress that does her no favors. The giant bedazzled bib on this dress completely weighed her down in the front, and that shredded looking hemline over tule reminded me of when Project Runway contestants were challenged to create dresses out of seatbelts. I would loved to have seen her something that either had more volume from the waist, or was a true column gown.

Dress aside, I am very happy for her that she won for Best Original Score. It was a category with a lot of contenders. What a great year to come out on top!

Salma Hayek .jpg
 

Regina King

For Better

Once again, Regina King looks like an angel. This shade of pink is so flattering on her, and the neckline and strap details are the perfect amount of drama. Just like last year, she is a great example of what a tasteful yet modern Hollywood red carpet look is.

Regina King in Versace.jpg
 

Billy Porter

For BETTER

While it’s going to take a lot to top his 2019 Oscars gown, Billy Porter once again made a splash in this metallic two-piece number. My favorite detail is the way that the skirt perfectly frames his strappy platform shoes. If I’d have styled him, I personally would have replaced his sunglasses with a headdress or flashier earrings.

Billy Porter in Giles Deacon Couture and Swarovski jewelry.jpg
 

Billie Eilish

For Worse

I know I’m going to get tomatoes thrown at me for this one. But I just couldn’t help it. If this were the Grammys or an MTV award show, I wouldn’t have minded this look, as I think it represents her personality well. But this is the Oscars! One of the dressiest nights of the whole year. Not to say she should be wearing a standard gown with her hair in a bun like everyone else, but she should look like Billie Eilish’s version of the Oscars. I would have loved to have seen her in an oversized suit that was a more dynamic shape, or wasn’t so long in the pant that she was stepping on the back of it. Or perhaps a more creative hairstyle that plays with the unique color combination she has going on and doesn’t look like she just woke up. I just feel like each and every choice made in this outfit was just for shock value, by (ironically) adding to her persona that she doesn’t care…but it instead came out looking hodgepodge and visionless.

And I don’t understand why she and her styling team make choices like this. Her style is already recognizable to the public, and she looked great in the outfit she wore during her rendition of Yesterday in the In Memoriam segment. I would have liked to see something in that vein on the red carpet too. She’s unique and talented enough to where she doesn’t need to rely on odd gimmicks to stand out.

 

Janelle Monáe

FOR BETTER

Of everyone in the Oscar’s audience, no one’s face was easier to spot on-screen than Janelle Monáe’s, framed in this beautiful draped Grace Jones-esque hood. Altogether with her dress, her ensemble was covered in 168,000 Swarovski crystals. In this futuristic almost space-age take on a vintage style, she looked regal and ethereal, while still being true to her show-stopping sense of personal style that we always look forward to every awards season. This gown was Steven’s personal favorite this year.

Janelle Monáe in Ralph Lauren.jpg
 

Natalie Portman

For BETTER

I love a sexy feminine dress with a bit of masculine edge. And this beautiful tuxedo cape combined with Portman’s dreamy golden lace Dior gown put it right over the top as one of the most memorable looks of the evening. Her choice of hair and makeup were also spot-on. Note: The cape’s lapel was stitched with the names of female directors who she is in support of. The cape was meant to be a subtle protest against the snubbing of female directors in the Best Director category.

GettyImages-1199754626.jpg
 

Arianne Phillips

For Worse

Renowned costume designer Arianne Phillips knows how to turn a look for film and stage alike. But this Moschino number felt like a letdown. For years there has been an on-going trend in fashion of draping pleated tule or sheer fabric over plus-sized models and clients. It always tends to dilute bright colors and cover up skin. I’m not saying that that’s necessarily why they chose this look for her, but that pleated fabric covering her is only looking like a major distraction, drawing my eye away from her face and great curves just to look at the center of her chest or the uneven black striping down her pink skirt and wonder what the hell the designer was thinking. I think we need to stop diluting bright colors on plus-sized women and stop covering them up so much. I want to see looks on them that accentuate their best features, the same way we dress those with model-eque body types in looks that accentuate theirs. (For instance what Rebel Wilson wore to the red carpet (not her Cats costume of course) is a great example of a dress embracing a plus-sized body type.) By the look of Phillips’ belt and clutch, I can tell there is a willingness to look edgy in this woman, and I would have loved to have seen that explored further.

Arianne Phillips in Moschino.jpg
 

Adam Driver and Joanne Tucker

For BETTER

My favorite couples ensemble of the night - hands down - was that of Adam Driver (nominated for Best Actor for his role in Marriage Story) and his wife Joanne Tucker. While Driver was dressed in your standard Oscars tuxedo, his hairdo and choice of facial hairstyle definitely made him stand out amongst the other penguin suits. And Tucker’s Oscar de la Renta gown was the perfect black and white compliment, giving me 50’s Old Hollywood chills. I wish it came with long black gloves! It just reminded me of something Grace Kelly would rock. Which says a lot about how timeless this silhouette and color palette is. I’d personally lose the necklace and tie her hair back to glam it up even further, but overall their distinguished and cohesive looks combined made the whole get-up one of my favorite moments on the 2020 red carpet. Call it understated if you wish, but I call it classic.

Adam Driver and Joanne Tucker.jpg
 

Kristen Wiig

For the Worst

When Kristen Wiig arrived on stage to introduce the categories of Production Design and Costume Design with Maya Rudolph, my first thought was “Wow she looks so great! I love her hair!” My second thought was sadly “What the f*** is she wearing?” I tried to understand this costume, you guys. I appreciate risks, I appreciate avant-garde, I appreciate a red gown with black gloves. So why was this outfit the one to make me cringe the hardest? There was just something so off-putting about it. The ruffles made her look so stiff. The fact that the ruffle didn’t continue to the ground or cover the shoes made it look incomplete. She was strangely shaped like an alligator tongue or something from out of a horror movie. And that blunt train of the cape looked like someone made it in 3 minutes. It was admittedly fascinating, but with no pay off. I feel like such simple changes could have been made to make it work. Maybe getting rid of the cape all together, and letting the ruffles continue to the bottom without tapering off would have helped. I think what made me so upset at it was the potential it could have had to be really interesting looking. And on the night that I thought she looked the prettiest I’d ever seen her, it was disappointing to look down and see this mess.

Kristen Wiig in Christian Louboutin.jpg
 

Saoirse Ronan

For THE BEST

This year, Saoirse Ronan’s hair and makeup was my absolute favorite of the evening. The baby bangs, the feathered pieces down the side of her face, the mix of intensity and subtlety in the color of her eyeshadow….it was perfection. In my opinion, it’s the best she ever looked - and that’s saying a lot! Moving own to the neckline, I felt that this deep plunging V was very flattering and well-constructed. I even liked the polarizing cream and black peplum element. But then we get to the pale blue moiré pattern jutting out from underneath, which confused me. I was almost horrified at the thought that on a night when everything looks so unbelievably perfect from the waist up, that that is what the rest of that dress looked like. Then I watched as everyone I knew and followed bashed it or praised it. I was on the fence for a bit, but when I got over the stark contrast between the black and cream and the moiré, I began to appreciate it for its color palette. The more I picked up the blue in her eyes and in her jewelry, the more it began to come together. And I love baby blue with cream and black. After sitting on it for a few more hours, it grew on me. And now I believe it was a good risk to take. It made her look so much more interesting than if the skirt was all black and cream, and brought out the color of her eyes. And while it never made it to the stage for a Best Actress acceptance speech, I think it won’t be long until one of Ronan’s next red carpet surprises does.

Saoirse Ronan Vogue.jpg
 

 And there you have it! A quite unorthodox turn-out for the Oscars. A lot of looks fell into the middle for me this year, with me not having a strong opinion one way or the other. So when I discovered ones that took my breath away (whether in delight or horror,) I knew I couldn’t pass up the opportunity to talk about them. Which looks were your favorite this year? What do you agree or disagree with me on?