CFDA Awards 2019: All the Gossip, Celebrity Encounters, and Tears From Inside Fashion’s Biggest Night

The first Monday in May certainly has a reputation in the fashion community and beyond, but the first Monday in June is nothing to sleep on, either. The 2019 CFDA Awards returned to the Brooklyn Museum this year to celebrate the best and brightest of fashion. This year, there was a bevy of high-profile honorees—from Jennifer Lopez to Barbie—and the added bonus of the new chairman, Tom Ford, making history as he succeeds Diane von Furstenberg. Here, a minute-by-minute breakdown of everything that happened at the 2019 CFDA Awards.

6:15 p.m. Before the inevitable pandemonium begins, Eileen Fisher is the first to breeze onto the pink carpet, wearing a cream-colored ensemble and bringing a much-appreciated sense of calm to set the tone for the evening. She remarks that she’s at the CFDA Awards for the everyday people, not just the celebrities. And for the everyday person, Fisher has one tip for adopting a sustainable lifestyle: “I always say stop and breathe before you buy. Like, just shop consciously. And that doesn’t mean we shouldn’t have things we love, it just means to slow down a little and think about what you’re buying. Sometimes I also say clean your closet before you go shopping.”

6:27 p.m. No one else has arrived, but just before everyone can start twiddling their thumbs out of boredom, Diane von Furstenberg walks across the carpet, carrying the same torch accessory she wore as a part of her 2019 Met Gala look. This torch, it seems, is the literal manifestation of the figurative torch she plans to pass on to successor Tom Ford.

6:30 p.m. Von Furstenberg rushes back to embrace Rodarte designers Laura and Kate Mulleavy as they talk about how excited they are for Lopez to receive her honor this evening.

6:50 p.m. Bebe Rexha, a first-timer at the CFDAs, can be heard talking about her newfound Game of Thrones obsession. “I just got into the fashion game, and I really love it. I’m new to it, I’m a baby. I’ve always been a tomboy, wearing all black.” The singer quips that while she only just started watching Game of Thrones this year and knows she’s late to the bandwagon, she’s excited to see Sansa Stark (Sophie Turner) IRL this summer while she tours with the Jonas Brothers. She also gives a little intel on what the Jonas Brothers are really like behind the scenes. “They’re actually very shy in person,” Rexha reveals. “Nick is very quiet, and he loves cigars. Like, a lot. Joe and Nick have always been super quiet, but when they go on stage, they’re a completely different person!” she adds before running off.

7:03 p.m. About 10 minutes later, Yara Shahidi can be seen powering through the red carpet with the perfect date on her arm: her mom.

7:15 p.m. Bernadette Peters makes her way down the carpet with designer Bob Mackie, the recipient of this year’s Geoffrey Beene Lifetime Achievement Award. Peters and Mackie have known each other for years, but they’re still willing to teach each other new things, especially when it comes to pop culture. Case in point: Peters tells Mackie he would love Killing Eve, and Mackie recommends HBO’s Gentleman Jack to Peters.

7:35 p.m. Stranger Things star Sadie Sink appears in a floral Kate Spade ensemble, ready to take on her first CFDAs. It’s summer vacation for the 17-year-old, but she’ll still have to work. “I’m traveling a lot, but that’s also great because when I’m traveling for work I usually get a few free days off. So I’m going to Tokyo, which I’m really excited for!” On the other hand, though, she’s looking forward to squeezing in some mini-vacations to hit the summer music festival circuit. At the top of her list? “Lollapalooza, I’m just gonna go all out!” she says, before adding that the number one musical artist she’s looking forward to seeing is Maggie Rogers, naturally.

7:40 p.m. Brandon Maxwell, nominee for the Womenswear Designer of the Year award, dabs his face with a cloth and cheekily asks his date, supermodel Lily Aldridge, if his bronzer is working. (It is.)

7:41 p.m. Shailene Woodley, wearing Jonathan Simkhai, skips the carpet, prompting everyone to woefully say that they had been looking forward to hearing some Big Little Lies season two updates from the actress if she had walked by.

7:44 p.m. La La Anthony sparkles in a blue sequined Ruthie Davis gown, gabbing about her recent casting as Brian Austin Green’s wife on the new 90210. “I was a fan, so when I auditioned and got cast I was so happy about it. I’ve been filming in Vancouver and came back for this!” she says, adding that she’s most excited to see Jennifer Lopez on the inside. “Her style is so versatile,” she says.

8:02 p.m. Dinner is supposed to have started by now, but of course Brooke Shields and her curls turn some heads.

8:04 p.m. Sander Lak of Sies Marjan and Kelela pop by. The designer takes a beat to talk about his favorite J.Lo look: “I’ve been obsessed with some of her Manolo Blahnik Timberland boots that she did in combination with Manolo. I think she did it in the “Jenny From the Block” video with the soft cargo pants? That’s probably my favorite.” The singer takes a moment to think about her favorite J.Lo videos: “I have a lot of respect for how much she’s done…we’ve known Jennifer Lopez’s name since she was a dancer on In Living Color. It’s interesting how talent just pushes through, irrespective of what that person’s doing. What she did aesthetically for me, let’s just talk about the videos. ‘If You Had My Love’ is a forever icy futurism reference, all white, sleek hard lines. But also ‘Waiting for Tonight’—I’ll never not be into that.”

8:06 p.m. Suddenly, the name that has been on everyone’s lips all night long has materialized: Jennifer Lopez and Instagram Boyfriend Alex Rodriguez are here in Ralph Lauren. Of course A-Rod dutifully steps into his role as Instagram boyfriend (now fiancé!), wielding his phone as they head upstairs so that dinner can officially commence.

8:55 p.m. Of course, getting upstairs is only half the battle—getting everyone to take their seats is a whole other story. Upstairs, different pairs navigate the room, wholly ignoring the fleet of waiters trying to pour drinks and place meals. There are BFFs and Booksmart costars Beanie Feldstein and Molly Gordon; sister models Lily and Ruby Aldridge; and, yep, the Olsen twins, one of the few duos to actually take their seats when instructed.

8:56 p.m. Hasan Minhaj is here to present the first award of the night (Menswear Designer of the Year), but not without a few jokes first about his lack of fashion knowledge. “I don’t know who a lot of you are,” he said. “Actually, I know some of you—you were on the sale rack.”

8:58 p.m. And the award goes to: Rick Owens! Unfortunately, our goth king is nowhere to be found. “Rick Owens missed his flight,” Minhaj explains. He’s not joking.

9:10 p.m. Michael Kors hits the stage to give a rousing and sentimental tribute to outgoing CFDA president DVF. She is, perhaps for the first time ever, momentarily rendered speechless. “By the way, she had no idea we were doing this,” says Kors.

9: 35 p.m. Clock it: 9:35 p.m., the first time Jay-Z’s “Empire State of Mind,” a CFDA staple, is played. It likely won’t be the last.

9:39 p.m. The Olsens take home Accessories Designer of the Year for the second year in a row. As it was last year, their speech is short and sweet, and nearly completely obstructed by the number of iPhones clamoring to get an Instastory of the twins.

9:40 p.m. Yara Shahidi is here to introduce the next award winner: ….Barbie. “This is the first time the award is bigger than the awardee,” she said. “And no, Barbie is not here to accept her award.” Neither is Kacey Musgraves, in what seems like a giant missed opportunity to recycle her 2019 Met Gala look.

10:19 p.m. Anna Wintour is presenting the International Award, underwritten by Valentino Garavani and Giancarlo Giammetti, to Alexander McQueen’s Sarah Burton. It’s perhaps the first time that a speech isn’t clouded by wisps of Juul smoke.

10:22 p.m. In hands down the best moment of the night, Brandon Maxwell tearfully accepts his Womenswear Designer of the Year award. He’s genuinely surprised. “I can’t believe this is happening. My pants are so tight and my bow tie is all wrong.”

10:33 p.m. Finally, the moment we’ve all been waiting for: J.Lo is here, accepting her award from Tom Ford. “I like to think it’s me [Rodriguez] can’t live without, but it’s really you,” she says to the designer. It’s a great speech—did you expect anything less?—ranging from her upcoming 50th birthday (“We don’t have to say it out loud,” she said. “We know.”) to a dedication to two departed friends, Kevyn Aucoin and Oribe, which had Lopez gesturing offstage for someone to give her a tissue. But, of course, she couldn’t accept a fashion icon award without mentioning that infamous Versace dress: “Ever since that night, green has been my lucky color.”