Inappropriate Outfits That Will Always Haunt Nikki Glaser

Nikki Glaser has had a number of fashun moments over the years, but let's just say not all of them have been the most, ahem, family-friendly. On the contrary, between very risqué numbers and super awkward wardrobe malfunctions, some of Glaser's lewks have been downright inappropriate. DW, though, because much of the time, she's been the first to poke fun at herself for them. 

@nikkiglaser/Instagram

We'll start with that time Glaser made an appearance on "The Tonight Show Starring Jimmy Fallon" and popped off right away (or her dress did, anyway). In an Instagram post about the situation, Glaser recounted, "After Jimmy introduced me, I opened my arms to say 'Hello Jimmy!' and my dress unsnapped. It's legit the first thing that happened. Nippy Glaser flashed everyone on the show and also my friends who were watching on the other side of my computer." Making matters worse, Glaser shared on "The Nikki Glaser Podcast" that she hadn't even planned to wear the dress at first, but decided to at the last minute because she'd tried it on at a fitting, realized it wasn't long enough for an awards show, but figured it would be fine for a Zoom interview.

Footage of the actual malfunction seems to have been scrubbed from the internet, so that's one perk — especially since the comedian admitted on her podcast that she was mortified about it, particularly because she went out of her way to keep things PG whenever she worked with Fallon. Glaser also said on the podcast that addressing it and poking fun at herself on social media was one way of coping with the tragic situation head-on. Even so, the fact that she posted it to her Instagram means the slip will live on forever. 

When Nikki Glaser hosted the 2025 Golden Globes, she did so in a fabulous golden gown (obvz) ... but let's just say the dress didn't offer much in the way of support. 

Granted, had Glaser stuck to standing upright (or, y'know, anything but filming a dramatic video to the soundtrack of Taylor Swift's "Who's Afraid of Little Old Me?"), the dress probably would have held up just fine. However, that was a compromise the famed Swiftie wasn't willing to make, and thus, the wardrobe malfunction backstage at the award show. 

To Glaser's credit, she posted the video to Instagram anyway, slapping on an "Oops" caption for modesty. Damage control, done and done. 

Moving away from the more glamorous aspects of her job, Nikki Glaser shared an Instagram snap of herself and then-podcast co-host Andrew Collins posing with a camel in 2022. Glaser was in a black minidress and snakeskin mules. 

The "Welcome Home Nikki Glaser" star certainly looked chic, but there's no question that her getup was inappropriate for the setting. Of course, she wasn't on the camel, but Collins' outfit of shorts, a hoodie, and sneakers certainly seemed better suited to the excursion, which only made her ensemble even more confusing. That said, the camel certainly seemed impressed, so maybe that's what she was going for. 

At the 2024 Emmys after-party, Nikki Glaser fully leaned into shock value, stepping out in a sheer, body-hugging, barely there gown that left little to the imagination. The transparent fabric sent a clear message: Glaser has zero problem courting attention. Make no mistake, this getup was obviously designed to turn heads — and kudos to her, because, uh, mission accomplished. 

The Valdrin Sahiti-designed frock drew a mixed reaction, with one Reddit user proclaiming: "I'd give that dress a 'big hell yeah'. How can something cover someone up so well, but be totally revealing? It's next level sexy!"

Nikki Glaser has never shied away from a miniskirt, and there's no denying she can rock one. That said, micro-minis coupled with physical comedy can make for a precarious pic.

As with the Golden Globes video and her mishap on "The Tonight Show Starring Jimmy Fallon," Glaser decided to share the snap on her Instagram, so perhaps the great lighting (and, again, her killer legs) meant she wasn't haunted, per se. Even so, we'd be lying if we said we didn't gasp an "Oh no, baby, what is you doing?" when we saw it. 

When Nikki Glaser shared the news that "FBoy Island" had been picked up for a second season on Instagram, she posted a GIF of herself from the show in a gold frock with billowy sleeves. Of course, Glaser probably didn't choose the dress for herself, but it was still all kinds of bizarre. The neckline on what was a fun, young dating show felt a tad matronly — and even when we realized it was a mini (of the micro variety, as usual), we still weren't sold on it being appropriate for the show or its setting.

Back in 2021, Nikki Glaser headed to Nobu with her friend David Spade, clad in an all-pink ensemble consisting of a satin blazer dress with fringe detailing and crocodile boots. Spade, meanwhile, donned jeans, sneakers, and a green sweater. 

We're certainly not going to use Spade's tragic dad-vibes lewk as the one to beat, but there's no question Glaser's super glam getup felt wildly out of place. It was also roasted by Us Weekly at the time, though Glaser was a sport about it, posting the article to her Instagram and thanking the mag for dubbing her a "good person" (albeit one in bad clothes). 

These days, Nikki Glaser is known for rocking some daring fits, so when we saw throwback snaps from the 2017 International Myeloma Foundation's Annual Comedy Celebration showing her in a prairie dress, you better believe we did a double-take. Granted, this was before Glaser's dramatic transformation, but even she joked about her outfit choice in an Instagram post from the night. "Thank you @imfmyeloma for letting me perform on my night off from fronting @florenceandthemachinee," she wrote — and honestly, she was spot-on. Of course, the dress being out of character for her didn't make it inappropriate, per se. However, it was a much more casual-looking ensemble than what many others donned on the evening.

Glaser has had a number of not-so-appropriate looks over the years, but she's certainly taken them all in her stride, and TBH, we think we love her more for it.