That said, we still saw some adventurous, boundary-pushing, eye-delighting fashion! Let's review:
Best Dressed
Billy Porter has just been teasing us, building up to this moment when he would come out of left field to completely SLAY the red carpet in a custom Christian Siriano velvet tuxedo gown. This is something we've never seen at the Oscars and yet it felt so right, and he wears it like he's nominated in every single category. He's having fun, but he's also truly blazing trails for everyone who wants to break down barriers in fashion. What a beautiful thing!
I double-taked when raven-haired Charlize Theron appeared, looking like her former Aeon Flux self. She looks so self-assured that if she announced she was creating a dating app just for Charlize stans, I'd be her angel investor. I definitely know the fit around the boobs was awkward — unsure what's going on there — but otherwise, I loved the delicate Wedgwood blue paired with the bite of her snake necklace, stunning earrings and that blunt dark bob.
When the camera hit J.Lo in this disco ball mirror mosaic gown by Tom Ford, I just had to clap. This woman applies a laser-like focus to red carpet dressing that is honestly a pleasure to behold. She never phones it in. She never dresses event-inappropriate. She is having fun, but also takes it seriously and I love her for it. This is hot, and in a night of a few silver-sequin gowns, hers took first place.
I can think of few people — actual royalty included — who possess the regal carriage of Angela Bassett. This SIXTY YEAR OLD fox is only getting better with age. The near-neon pink of this Reem Acra was especially lovely with her skin tone, and I love the drama of her oversized sleeve. Her pink earrings would have made Barbie envious.
Emma Stone has been giving me a case of the blah's for her past few fashion outings, but I loved how utterly unique and vibrant this Louis Vuitton gown was! Yes, it absolutely looks like a formal waffle cone costume, but I really do love the subtle color — it is burgundy? it it burnished copper? — and the armor-like quality of the shoulders. She stuck the landing for me.
This is how you want to look when you know your picture is about to go down in Oscar history. Regina King played it a bit safe, but elegant and timeless, in this beautifully draped white Oscar de la Renta gown. She looks like an angel!
Yes, Rachel, yes! Give me futuristic rubber sex goddess/bishop couture! I did a quick Google search before the show to remind myself of her previous red carpet fashions and they were typically simple, sleek, neutral colors. Nothing could have delighted me more than to see her in the audience wearing this truly unexpected and incomparable red Givenchy couture. It's rare for me to see something that feels different, and this was different.
I love when Amy Adams taps into her Jessica Rabbit side and brings va-va-va-voom glamour. This delicately patterned Versace gown hugs in all the right places, boosts the girls and might be one of my favorite gowns she's ever worn. Now, let's get this girl a damn Oscar already!
You can't really go wrong with well-draped sparkly fabric, but Emilia Clarke's Balmain has the most beautifully subtle color. It looked silver in some light and hinted of lavender in photos, like a magic trick.
Newcomer Kiki Layne ("If Beale Street Could Talk") maybe didn't get as much attention this awards season as I would have expected, but she made up for it by pulling off a just-daring-enough soft pink gown by Atelier Versace. She looks like the Winged Victory of Samothrace statue at the Louvre! This gets me excited to see her around in the future.
The hills are alive, for crazy rich Asians!!!! How could you not melt for the sheer joy of Constance Wu in canary yellow custom Versace, twirling her pleated chiffon like a little girl in a recital? You can't really tell in this picture, but the neckline was trimmed with lovely rhinestones. The look itself felt a little like a repeat of my favorite Michelle Williams look from 2006, but you know what, it's been 13 years. I'll allow it.
Gemma Chan wore a pink highlighter smocked parachute by Valentino and somehow managed to look effortlessly glamorous and chic. She gives me strong Audrey Hepburn vibes, just with the way she carries herself with complete grace. Most of us would drown in this, but she makes it look natural.
If you were holding out for a hero to combine all the trends — one-shoulder, ruffles, color — Jennifer Hudson is here for you in this chic Elie Saab. It's simple, but not boring, and the color pops. This felt perfect for her role as a performer/former winner.
Helen Mirren is having more fun than anyone else in this multicolor, layered Schiaparelli gown. It manages to be fit for a Dame and more fun than your prom dress. She was twirling the skirt up and down the red carpet, living her best life.
Michelle Yeoh has carved out a style for herself — classic, but a little bit sexy; mature, but not mumsy; trimmed and detailed. This silver-and-gold Elie Saab was even more beautiful on the telecast than it appears here, and she looked luminous. Her skin was glowing!
Basic black doesn't have to be boring, and Allison Janney brought sexy back in this sleek take on a tuxedo motif by Pamela Rolland. Morticia Addams is a style icon for a reason! Bonus points for one of the best necklaces of the night, a fun combination of rubies and diamonds.
Captain America, at your service! Chris Evans was at the ready to help those who needed it, whether it was assisting Regina King up the stairs or providing a steady arm for Jennifer Lopez. His ice blue velvet blazer by Ferragamo just made him look even more like Prince Charming.
After watching the march of the pink gowns, I said, "Where are the pink tuxes" and lo and behold, Jason Momoa appeared. There's something delightful about this manly man, the former Khal Drogo for chrissakes, tucked into pink velvet with a MATCHING SCRUNCHIE ON HIS WRIST. It's so wrong, it's right.
Yeah, I know what you're thinking. Have I truly lost it? But Spike gotta Spike, and at this point in my Oscar-watching days, I welcome the vision of an iconoclast so committed to his Look. Custom gold Air Jordans paired with a Prince-themed necklace paired with purple specs and the loudest accessories on the red carpet? You do you, Spike boo.
Best Worst
The best-worst category is reserved for someone who really does the most to try to get the most attention, someone straddling that line between "wow she really went there!" and "wow, she really went there." Linda Cardellini, a person who has no defined red carpet style history, decided this was her moment to really assert herself and WOW SHE DID. For me, this feels less "designed" than "thrown together" and frankly, feels like a little girl put it together out of hot pink loofahs. Weirdly, Twitter seemed to like it? I bet it was fun as hell to wear, though, and she looked very proud of herself.
Make it Fashion
This category is for the iconoclasts who never rest on their laurels. Elsie Fisher has turned up on red carpets in Thom Browne suits that give me Tatum O'Neal-winning-for-Paper Moon vibes. It's completely nontraditional, but she looks so confident and clear. Who among us could say the same at that age? It's not what I would wear, but it's not the worst thing either.
Damn you, Sarah Paulson! How do you have me second-guessing whether this Brandon Maxwell dust ruffle combo is great or weird AF? Only in her capable hands is this maybe working.
Chadwick Boseman is having so much fun with his evening wear, and this was no exception! I'm not sure I 100% understand what I'm looking at — is it floor-length tux tails? He's pulling it off, though.
Nicholas Hoult wore a draped tux that was basically a reinvention of the whole idea of the tuxedo, and both Ashleigh and I gasped in my living room. It was so different and fresh and, like so many of the looks this year, pushed the boundaries of fashion. That's exciting!
Good
Oh, Glenn. Man, I really thought she was a lock to win! And, bless her, but clearly her style team thought so as well. Dressing literally like an Oscar has worked for a shocking number of past winners — Meryl Streep, Sandra Bullock, Emma Stone — so why wouldn't it work for the damn WIFE? Let's take this as a lesson to all of us: it never ever hurts to dress for the job you want, because you'll still look good no matter what. I did not love some elements of this Carolina Herrera look, particularly the damned useless pocket flaps. But ultimately, it was a career best for her.
I had this grand fantasy that Lady Gaga was going to set some new high bar for Oscar fashion, something akin to Rihanna at the Met Ball every year. I was expecting a train that stretched two miles, or a headpiece that out-Cher'd Cher or a Dior Museum piece or something. This Alexander McQueen is fine. I like the exaggerated hips, and the gloves are a nice, dramatic touch. The real savior of the entire ensemble is the infamous Tiffany Diamond, never before worn on a red carpet. I imagine her goal was to make it the star of her look, and I can empathize.
I mean, that's a dazzler.
I like the casual elegance of this crinkly gold Brock Collection gown on Danai Gurira. Her skin is glowing, and her headband gives it a jolt of fun. Definitely her best look this season.
Brie Larson looked cool and fresh in this icy sequined Celine gown and tousled waves. It reminded me of some of Naomi Watts' best looks — very modern and sleek. It wasn't my favorite of the silver sequin numbers, but it was a good showing.
Laura Harrier is a burgeoning style star, and I liked this simple blue Louis Vuitton ensemble even if it did make me scratch my head a bit. I think it's two pieces, but it's not immediately obvious and it almost makes you want the designer to commit to either one or two clearly defined parts. All told, it's a sweet, can't-miss pick for a newcomer.
Octavia loves a full, sparkly navy gown as much as I love a black sweater and why not? We know what works. This Christian Siriano fits beautifully, and the fabric has great sheen, but the overall look feels underaccessorized.
Tessa Thompson's black and gold tube gown is classic Chanel, blessedly well-fitted and not too boring. The accessories and makeup were perfectly complementary. She can't miss with that bone structure, either.
Everybody loves a Cinderella story, and I especially love when Cinderellas come to the ball dressed exactly like my favorite Disney Princess. Roma's Yalitza Aparicio looked so lovely in this sweet and simple star-studded Rodarte gown.
Legendary Cicely Tyson, 94, brought high glamour to the red carpet, proving you don't age out of having fun with fashion. She looks like the grown-up version of Tessa Thompson's look, and positively statuesque!
Letitia Wright was classic and demure in her delicate foliage-pattern Dior Haute Couture accented with some of the best earrings of the night, a pair of yellow diamond sparklers. This is a little simple for my taste, but it seems perfectly her, and she looks like a graceful ballerina.
Man, you know it's a wild night when Marie Kondo is one of the best-dressed people there! Pardon the joke, but it's required: this gown sparks joy.
This J. Mendel gown on Marina de Tavira (of "Roma") was one of my favorites on the runway, so I was happy to see it on the red carpet! I'm a sucker for layers and layers of pleated tulle, and it looked like a 50's prom dress in the best type of way.
I deeply appreciated how much the non-acting category winners really brought it with their fashions this year! When I was a kid, those serious filmmakers were more likely to be wearing off-the-rack department store formalwear, but now they're style stars! It's a bit wrinkly and messy, but I appreciate the drama of production designer Hannah Beachler's dramatic orange coral reef of a gown.
Meh
Let's be clear: this is one of Melissa McCarthy's best looks ever!! But man, it gives me the mehs. What does it need? More dramatic jewelry? Commit to a deeper blush color on top? A different hairsdo? Something just isn't working for me, but I can't figure out what.
I dunno, I guess I just expect gosh-dang supermodels not to dress like a couture interpretation of the leg lamp from A Christmas Story. Irina Shayk looks fine, I guess.
I just couldn't get fully on board for this voluminous Christian Siriano gown on Kelly Ripa. She's such a tiny little person that she seems to be swimming in fabric. But also, the fabric didn't seem to photograph well and at a glance, it almost looks like she's wearing embroidered chambray, as though she's queen of the rodeo. It actually appeared much prettier than that on screen, but I think the fine detail of those tiny flowers is just too small to render properly on telecast.
This eggplant Rodarte gown was a bit muted for Laura Dern, but completely non-offensive. It also wasn't very inspiring either and doesn't even scream "Rodarte," who are normally known for their delightful eccentricity. In this gown, she'd be the very best dressed guest at a formal wedding.
There's something about this Lucy Boynton look that just isn't adding up for me. Her make-up story and current shade of blonde washed her out to the point she looks borderline consumptive. The dress itself is an interesting color, but the style feels very mature, and a little bit Gilded Age-meets-Dynasty. She deserved better.
I honestly don't know how I feel about this Giambattista Valli on Maya Rudolph. On one hand, it truly captures the zany essence of her, and I LOVED her multicolored earrings. On the other hand, this is very crazy aunt garden party. It's a lot of look.
Meanwhile, Tina did what Tina does: basic gown that could be custom Vera Wang or could be from Dillards. It's fine!
I liked the way Serena Williams' red bodice insert sparkled, but otherwise, this isn't a particularly memorable Armani Prive gown.
SZA is cosplaying as a member of Marie Antoinette's court, and I just am not really moved by it in one way or another. It's not bad enough to be the worst and it's not great, so here it is, middling.
I like the idea of a new take on the formal pantsuit, and I liked the faint purple sparkle of this fabric, but ultimately the fit of this DSquared suit makes Awkwafina look both shorter and wider than she really is. It looks like it wrinkled so easily, which is just a bummer. I think cutting the bow would go a long way to simplify the look, or even putting her hair up so it doesn't look like she's neckless.
Worst
Oh Olivia Colman, queen of my heart! I volunteer as tribute to harness your red carpet energies in time for your inevitable Emmy wins after the new season of The Crown. This custom Prada is a real head-scratcher, suggesting she maybe got tangled up in a bolster of fabric and couldn't be dissuaded to remove it. The overall look is fit for Mother Nature, if she was an empty nester who's taking ceramic classes and advocating for backyard chickens at City Council sessions.
I mean, gosh, is this maybe closer to a best-worst? Frances McDormand has more BDE than most entertainers, living or dead. Even though this shapeless ruffled taffeta smock paired with custom citron Valentino X Birkenstock shoes is truly an assault against everything we thought we knew about fashion, it's also so unabashedly her that I'm grateful I got to see it. Look at that saunter!
In this schoolgirl look, "Can You Ever Forgive Me" screenwriter Nicole Holofcener could be starring next in your community theater's gender-switched adaptation of "Spring Awakening."
I groaned LOUDLY when my sweet angel Amy appeared in this ho-hum Alberta Ferretti black tux that doesn't even look comfortable. Her aggressive allergy to focusing her fashion inclinations is so exhausting when you love her as much as I do.
Adam Lambert's exaggerated cuffs make this ensemble look less Fashion and more Vaudeville. I half expect that flower to squirt water while he sings "Mr. Cellophane" from Chicago.
Diane Warren, you lovable kook! Her commitment to whacky fashions even Elvis would reject is truly admirable, and even more so when you consider how incongruous her wild fashion sense is compared to her truly schmaltzy songwriting (know that as I'm typing this, I'm also LIVING for most of her songs). The chains around her neck make it look like she's an anchor just dropped from a spaceship.
Lisa Bonet looks amazing, especially considering her daughter basically looks like her younger sister. But I cannot wrap my brain around this ensemble that appears to be flower netting stretched over a tank top and paired with boots fit for Westworld.
You almost have to admire Pharrell's commitment to just completely flouting the mere concept of dressing up, even if it would bother me deeply if someone showed up to my formal event in a camo Angus Young suit and mid-length white socks. He looks like he's just daring you to send him to the principal's office.
Normally I don't really feel like it's fair to be overly critical of the not-famous dates at these things because, let's be real, they don't have the same access to designer fashion. But Keegan Michael Key's wife Elisa Pugliese is a couple colors away from being a walking advertisement for the Polaroid logo and I can't unsee it.
Likewise, John Mulaney's lovely wife Annamarie Tendler wore a very zany straight-from-the-60s neon-feathered brocade number that just looks like a dying plant.
Costume designers do get a pass to a certain degree, because we want them to be bonkers and Sandy Powell is a legend. At its best, this looks like a David Bowie tribute. At its worst, this looks like a formal, silky Hamburglar tux.
I really am wrestling with this look by Amatus Sami-Karim (wife of Mahershala Ali). It's kind of majestic and bold in a way I want to root for, but it also looks like a selection from Miss Frizzle's undergrad couture show before she got hired to helm the Magic Schoolbus.
Lastly, I typically stick to strictly Oscars red carpet fashion because if I ventured into after-party fashion, I'd never get to sleep. There's just too much wrong happening there. But it had to be noted how utterly desperate Kendall Jenner is wearing this strip of fabric — er, gown — that requires built-in panties just to keep her goodies from showing. It gives the effect of a formal old-fashioned pad-and-belt combo, like they used before they came up with pantyliners. This isn't the first time she's shown off her pelvic bone, as though she's doing sponsored content for her waxer. It is less fashion than it is an ad for double-sided tape. I don't enjoy this style of "daring," because it's lowest common denominator. Her face looks great, though, and if she wanted everyone's eyeballs on her, mission accomplished.
