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The Biggest Night In Fashion Certainly Lived Up To Its Name

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Every year, the bar is set very high for the CFDA Awards when it comes to pivotal red carpet moments. It's not the biggest night in fashion for nothing (sorry, first Monday of May). Over time, we've seen Seth Meyers don see-through Marc Jacobs circa 2012, the return of SNL favorite Mango on Alexander Wang's arm back in 2014, and, perhaps most memorably, Rihanna decked out in crystals — and barely anything else (which also transpired in 2014).

Here's the CFDA Awards equation: Take the glitz and glamour of Hollywood's awards season and up the ante with an attendee list filled with the biggest style risk-takers out there (think icons from Alexa Chung to Tilda Swinton) then add the biggest design talents around and their muses. The night is all about celebrating inspiring, boundary-pushing fashion — and invitees don't take the responsibility lightly.

The night was certainly one for the books, from Brandon Maxwell's heartfelt speech (that had even Naomi Campbell daintily wiping away tears) to Beyoncé's surprise appearance to accept this year's CFDA Style Icon award. But it all started way before host Joel McHale even took the stage: First, there was the red carpet, which was essentially a namecheck of all the most zeitgest-y designers in the biz. Olivia Wilde and Karlie Kloss smiled ear-to-ear in their Rosie Assoulin ensembles. Gia Coppola, Hari Nef, Bee Shaffer, and Anna Wintour repped the new Gucci guard. The Olsen siblings (twins Mary-Kate and Ashley and younger sister Elizabeth) matched in all-black looks by The Row. (Seriously, when is that family adopting us?)

Some call it the Oscars of fashion. Others think of it more like an industry-wide graduation. Whichever analogy you prefer, there's sure to be excellent style moments each year. Ahead, we round up some of the best looks of the night.

What sparkles brighter — Karlie Kloss' positively contagious smile, or the Swarovski crystals on her Rosie Assoulin gown? (This one's a draw.)

Kloss is wearing a Rosie Assoulin dress and Atelier Swarovski jewels.

Photo: Jamie McCarthy/Getty Images.

Naomi Campbell can't stop smiling — maybe because she knew her gown (and her gown's designer, Brandon Maxwell) was a sure winner.

Campbell is wearing a Brandon Maxwell dress.

Photo: Jamie McCarthy/Getty Images.

"Suit up!" said How I Met Your Mother 's Barney Stinson...and Emily Weiss while donning this Baja East set.

Weiss is wearing a Baja East suit.

Photo: Jamie McCarthy/Getty Images.

Joan Smalls switched up her look, but not her go-to designer: The model stepped out with a blunt new 'do and a draped, off-the-shoulder Givenchy number.

Smalls is wearing a Givenchy dress and Eddie Borgo jewels.

Photo: Jamie McCarthy/Getty Images.

The Olsen coven had a strong showing last night in head-to-toe The Row — and we want in.

Mary-Kate and Ashley Olsen are wearing The Row clothes, shoes, and bags; and Sidney Garber jewels.

Photo: Jamie McCarthy/Getty Images.

As if Kirsten Dunst's mermaid-esque Rodarte dress didn't already feel plucked straight out of a fairy-tale, the actress one-upped herself with a dangly earring featuring a real orchid, courtesy of florist-to-the-stars Joseph Free.

Dunst is wearing a Rodarte dress.

Photo: Jamie McCarthy/Getty Images.

Ciara continues her red carpet-slaying streak in a deconstructed princess gown by Roberto Cavalli and strappy Stuart Weitzman heels.

Ciara is wearing a Roberto Cavalli dress and Stuart Weitzman shoes.

Photo: Jamie McCarthy/Getty Images.

As CFDA board chairman, Diane von Furstenberg had all eyes on her at last night's show. The legendary designer kept it classic by revisiting the tried-and-true LBD, and switching things up with a white-speckled sheer top and layered, drop-waist hem.

Photo: Jamie McCarthy/Getty Images.

A perk of being Tanya Taylor's date to the CFDA Awards? Gillian Jacobs gets to don a gorgeous, custom color-blocked pencil-fit dress for the occasion.

Jacobs is wearing a Tanya Taylor dress and Delfina Delettrez rings.

Photo: Jamie McCarthy/Getty Images.

Rosie Assoulin assembled quite the crew for the CFDA Awards: The designer herself stepped out in a pajama-esque metallic rainbow set, while her date, Olivia Wilde, opted for a body-hugging, one-armed gown with side cutouts.

Assoulin and Wilde are wearing Rosie Assoulin.

Photo: Jamie McCarthy/Getty Images.

Tilda Swinton is always the coolest person on any given red carpet. This was certainly the case at the Hammerstein Ballroom, where the actress arrived in a shoulder-padded patterned top and tracksuit-like trousers.

Photo: Jamie McCarthy/Getty Images.

The Gucci table was the place to be last night — and Bee Shaffer held court in her Alessandro Michele-designed landscape blue gown, featuring the brand's (new) signature tromp l'oeil sequin collar.

Shaffer is wearing a Gucci dress and shoes.

Photo: Kevin Mazur/WireImage.

Jourdan Dunn's fringed, beaded Jonathan Simkhai gown feels very flapper-esque — and it made for some really great Boomerangs, too.

Dunn is wearing a Jonathan Simkhai dress and Eva Fehren jewelry.

Photo: Kevin Mazur/WireImage.

Alexa Chung declared it "leather weather " in New York last night with her zipped-up Prabal Gurung frock.

Chung is wearing a Prabal Gurung dress.

Photo: Jamie McCarthy/Getty Images.

Jillian Hervey of Lion Babe was basically summer incarnate in this vibrant floral Adam Selman slip dress.

Hervey is wearing a Adam Selman dress.

Photo: Jamie McCarthy/Getty Images.

Anna Cleveland goes for a glam-rock vibe in a shimmery velvet spring '16 Rodarte number.

Cleveland is wearing a Rodarte jumpsuit, jacket, and shoes.

Photo: Jamie McCarthy/Getty Images.

Jasmine Tookes reps the silhouette of the season, thanks to this high-neck, all-over embellished midi-dress.

Tookes is wearing Swarovski jewels and bag.

Photo: Jamie McCarthy/Getty Images.

Hilary Rhoda's regal, ombré Monique Lhuillier gown even came with a crown.

Rhoda is wearing a Monique Lhuillier dress.

Photo: Jamie McCarthy/Getty Images.

We can't decide what we like more: The playful color combo on Jamie Chung's dress, or the fact that it's from Banana Republic (and we'll be able to shop it in August).

Chung is wearing a Banana Republic dress.

Photo: Jamie McCarthy/Getty Images.

Olivia Culpo knows that the fun doesn't really start until you put your party skirt on. In her case, it was the feathery bottom of her Kate Spade blazer dress that kicked off the festivities.

Culpo wears a Kate Spade dress and Mattia Cielo jewels.

Photo: Dimitrios Kambouris/WireImage.

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