The Dumbest, Brightest, and Most Unintentionally Hilarious 2019 Celebrity Halloween Costumes

By Maria Sherman | October 28, 2019 | 3:30pm

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The Dumbest, Brightest, and Most Unintentionally Hilarious 2019 Celebrity Halloween Costumes

Halloween has yet to take place, but judging from my Instagram feed, all the good parties were on Saturday night. Judging by the Instagram accounts of celebrities, they agree. I mean, just look at Kate Beckinsale whimsically walking through a Rite-Aid in full Breakfast at Tiffany’s Audrey Hepburn/Holly Golightly attire, next to a very sparkly pal, Jonathan Voluck, as Elton John? The same costume worn by Harry Styles last year? I’m inspired.

It is time for Jezebel’s annual celeb Halloween costume roundup. Join me.

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Jessica Biel, after announcing she is somehow unfamiliar with the music of *NSYNC (was she asleep from 1999 – 2002?) dressed up like husband Justin Timberlake in his iridescent snow suit golden era. JT was a microphone:

Halsey and new beau Evan Peters went as Sonny and Cher, which is a good costume:

She was also Marilyn Manson:

Nicki Minaj went as Margot Robbie from that movie:

Kylie Jenner and her best friend of the moment Stassie Karanikolaou dressed up as Madonna and Britney Spears’ 2003 VMAs smooch:

And Kylie’s one-year-old daughter, Stormi Webster, went as… Kylie. Is this some weird narcissistic game I cannot even begin to unpack?:

Kourtney Kardashian was Ariana Grande:

Demi Lovato was Pennywise (from IT, not the band. The band would’ve been funnier):

She was also Marie Antoinette:

Gabrielle Union, who consistently kills the Halloween game, referenced her Bring It On days… and brought her daughter into the mix:

Pregnant Ashley Graham was pregnant Jessica Rabbit, and it’s kind of great:

Cardi B, heal me:

Paris Hilton was a clumsy showgirl? Saloon… lady? It’s vague:

Nina Dobrev was the bad guy—a very good Billie Eilish:

Liam Payne, formerly of One Direction, was Clark Kent:

Social media celeb Bretman Rock absolutely killed it as Violet Beauregarde from Charlie and the Chocolate Factory:

Living meme Rickey Thompson was The Fifth Element’s Ruby Rhod, which is not too far off from his day-to-day personality:

Tana Mongeau and Jake Paul were whatever the hell this is:

And now for the reality TV stars. Lisa Rinna wore what is probably the Fashion Nova version of Jennifer Lopez’s famed Versace dress, and I have to respect that:

Bachelor in Paradise couple Caelynn Miller-Keyes and Dean Unglert dressed as each other:

Former Bachelor (well, he’s still a bachelor, but that’s a conversation for another time) Nick Viall decided to dress up as forthcoming Bachelor, pilot Peter. Now that’s what I call branding:

Happy Halloween, from them.