10 Celebrities Who Won Halloween (And 10 Who Lost)

Every year at Halloween people tune in to find out what their favorite celebrities will dress up as. These are people who are trendsetters— if a celebrity does it, fans will live vicariously through them and dress just like them every chance they get. It’s no different come Halloween time; the costumes and outfits are just more extreme.

There are a few celebrities who take it to the next level every year and always kill it, like the self-proclaimed "Queen of Scream," Heidi Klum, who spends half a day putting on her complex, insane costumes. There are other celebrities who just throw on any old thing and couldn’t be bothered— they’re barely even participants of the festivities.

With so many celebrities dressing up, it’s hard to narrow down the winners from the losers. But we have a pretty good list here of 10 celebrities who won Halloween this year, and 10 who lost. You be the judge.

20 Won: Heidi Klum (Princess Fiona)

via Halloween Life

Heidi Klum is a master Halloweener. She always goes all out for her costumes, sparing no expense. It doesn’t matter that she’s a model— sometimes she’ll use that to her advantage by going the other way and being someone “ugly,” such as Princess Fiona from Shrek this year, which she totally ruled. She also had a prosthetic zombie-alien outfit that was quite spooky and took half a day to apply.

19 Lost: Ellen DeGeneres (Cardi B)

via Rolling Stone

Ellen DeGeneres is loved and adored by her fans, but we just can’t back this one. When she had Cardi B on her talk show, she dressed up as “Cardi E,” which was a carbon copy of Cardi B. She even twerked in front of the music star. The problem was that Ellen just couldn’t quite cut the mustard in the suit, with the prosthetic big boobs and wig. At least Cardi B liked it, though.

18 Won: Kate Beckinsale (Holly Golightly)

via Medium

Although the setting for her costume wasn’t spectacular— at 7/11 shopping for snacks—Kate Beckinsale’s take on Audrey Hepburn’s Holly Golightly, from Breakfast at Tiffany’s, was completely spot-on. The dress is form-fitting and tight, Beckinsale had the perfect body for it, and the extended cigarette, broad-brimmed hat, and plethora of pearl necklaces only made it even better.

17 Lost: Jessica Biel (Justin Timberlake)

via Page Six

We understand what Jessica Biel and husband Justin Timberlake were going for here, but it just doesn’t work for us. Jessica tried to dress as early JT, and JT dressed as… an oversized microphone. But Jessica doesn’t look anything like JT (which isn’t surprising), and she seems to be trying a bit too hard. The main reason this is a fail is because of Justin’s completely befuddled, exasperated expression. You can tell he got talked into this one…

16 Won: Kelly Clarkson (Winnie Sanderson)

via People

Singer Kelly Clarkson channeled her inner witch with an ode to the Hocus Pocus witch, Winnie Sanderson. She debuted the look on her self-titled talk show and even sang the witch’s signature tune, “I Put a Spell on You” in character! She really cleaned up with this one, and even commented on her Instagram picture (which got 150,000 likes), “Oh look, another glorious morning. Makes me SICK!”

15 Lost: Khloe Kardashian And True Thompson (Cruella DeVil And Dalmation)

via Allure

Now, don’t get us wrong, Khloe Kardashian looks absolutely amazing and ravishing in this Cruella DeVil outfit from 101 Dalmatians. She not only looks like the character, but has her own spin on the evil dog-skinner. The problem we have is turning True Thompson into one of the Dalmatians. While true looks totally adorable, we can’t help but realize that as a Dalmatian… mom is set out to skin her! And that’s no good.

14 Won: Kylie Jenner (Marilyn Monroe)

via E! News

While her sister Kim opted for pink too (trying to pull off Legally Blonde this year), Kylie Jenner really hit it out of the park with her take on Marilyn Monroe. This is definitely one for the books, from the silk gloves to the diamond jewelry (a girl’s best friend), and that alluring look in her eyes. The plump lips are spot-on, too. The makeup mogul transformed herself in this picture, much to the delight of 4.7 million fans (that’s how many likes her Instagram picture of the costume received).

13 Lost: Demi Lovato (Pennywise)

via Lifestyle

Former Disney star Demi Lovato brought her A-game by dressing as Marie Antoinette, which was stunning and amazing. But her portrayal of Pennywise from the 2017 remake of It just doesn’t do it for us. Yes, the costume looks nice and she looks amazing, but that’s part of the problem: the “sexy” character outfit is so overdone that it’s just not that alluring any more, even when a superstar does it. Lovato’s mother donning a yellow raincoat and dressing as Georgie was pretty good, though.

12 Won: Neil Patrick Harris And Family (Van Gogh, Salvador Dali, Frida Kahlo, Andy Warhol)

via distractify

Neil Patrick Harris managed to win Halloween this year not because of his costume (which is great), but because of the combined factor of doing the gig with his family, in a sophisticated twist. Neil and David Burtka always take it up a notch come Halloween, and they didn’t disappoint this year, showing a portrait of himself as Vincent Van Gogh, David as Salvador Dali, and their kids as portraits of Frida Kahlo and Andy Warhol!

11 Lost: Ashley Graham (Jessica Rabbit)

via Daily Mail

Model and television presenter Ashley Graham did a fun, cheeky costume, but it’s one that’s been done far better before. Heidi Klum, for instance, took up this challenge a few years ago and killed it. But Ashley’s version of Jessica Rabbit from Who Framed Roger Rabbit? is really, as Wonderland Magazine put it, “Jessica Roadkill.” The energy is lacking, the prosthetics don’t really work, and the pregnancy isn’t doing her any favors— not that she can help that.

10 Won: Ciara And Russell Wilson (Beyonce And Jay-Z)

via Irish Mirror

There simply aren’t enough good things to say about this concerted effort between Seahawks’ quarterback Russell Wilson and superstar Ciara. They dressed up as Beyonce and Jay-Z from the “APES***” music video, and completely killed it. Their costumes made ESPN headlines, in fact, and Wilson was even interviewed on the matter. It was all in good fun, of course.

9 Lost: Cardi B (Nurse)

via Hollywood Life

This is another one that is overplayed and done too often, which makes it unappealing. Yes, Cardi B looks really great as this sexy nurse— that’s the whole point– but could there be a less original costume? We’re hoping she goes all out next year, because this one was playing it safe, and that’s not what people want to see from Cardi B!

8 Won: Nicki Minaj (Harley Quinn)

via People

Superstar Nicki Minaj managed to turn a tired, dead-horse Halloween costume into something fantastic, mainly because she looks spot-on as the character of Harley Quinn. She’s ready to be cast in the next movie, we’re convinced, and she’s even showing more curves than the Suicide Squad Harley does. Husband Kenneth Petty also didn’t do too bad as Heath Ledger’s Joker.

7 Lost: Liam Payne (Clark Kent)

via FarmWeek

Liam Payne might look a bit like Clark Kent, but so do a lot of people. The former One Direction star threw on the Superman shirt, put on a button-down over the shirt, opened it up, and called it a day. He pairs his costume with Dior, which is strange, and it just isn’t that much of a “costume.” It’s not great, it’s not terrible, but it could be a whole lot better, which is why we’re ragging on it. You can’t compare this to, say, Stormyz showing up as Jason Vorhees in full regalia from Friday the 13th, at the same event.

6 Won: Hailey Bieber (Lola Bunny)

via PopSugar

Hailey Baldwin, or I guess Hailey Bieber as she’s now recently known as, stunned fans with her portrayal of Lola Bunny from Space Jam. Not only did she pick a classic movie to choose her costume from— youngsters might not even know what Space Jam is, and that’s a shame— but she also looks nearly identical to the character. And that’s saying a lot, because the character is a rabbit!

5 Lost: Bella Hadid (Fred Flintstone)

via Ok! Magazine

Bella Hadid certainly stunned people with this decision, but that’s not necessarily a good thing. The model showed up in a Fred Flintstone costume, but Bella tried to make it a bit “chic” and sexy, and that just doesn’t work. Her bone-shaped earrings are a nice touch, but really, no one wants to see a gender-swapped, cleavage-bearing, come-hither-looking Fred Flintstone. No one asked for that.

4 Won: The Weeknd (The Joker)

via Metro

Wow, who knew that The Weeknd took his Halloween costuming so seriously? His portrayal of The Joker from Tim Burton’s Batman from 1989 is absolutely killer. He nabs Jack Nicholson’s attire, face-paint, and even that creepy look that (we thought) only Nicholson himself could do. It turns out the singer is a definite runner-up for “best-costumed celebrity” this past Halloween.

3 Lost: Kylie Jenner (Ariel)

via pagesix.com

Kylie Jenner already stunned people (in a good way) as Marilyn Monroe, and she should have stopped while she was ahead. This is another one that is overdone and overplayed: dressing up as a “sexy” Ariel from The Little Mermaid. Sure, her seashells are a bit bigger than the cartoon’s, but this look is too generic to be called a winner.

2 Won: Jason Momoa (Elvis Presley)

via Just Jared

Jason Momoa can basically do no wrong, but we have to admit that his portrayal of The King of Rock, Elvis Presley, is pretty darn impressive. He made sure that Elvis was in the building wherever he went, shining in this pink, bedazzled jumpsuit and cape. Here he’s in full form on The Ellen DeGeneres Show, wowing the screaming audience with his killer good looks and jokey costume.

1 Lost: Gabrielle Union-Wade (Clovers Cheerleader)

via Standard

We understand what Gabrielle Union-Wade was trying to accomplish here, and she totally did: she showed that she’s still got it as the Clover Cheerleader. She looks spot-on, exactly the same, like she hasn’t aged a day in a decade. But it’s not really a costume when you played the part in a movie. She just had to reach into her wardrobe, find a part she played before, and throw it on. Not very original. Her child as a backup cheerleader is super adorable, though.

Sources: harpersbazaar.com, wonderlandmagazine.com, cnn.com

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