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Halloween is that magical day when everyone gets to play dress-up, watch scary movies, and soak up all the spooky vibes. Sounds like a blast, right? But sometimes, costumes don’t just raise eyebrows - they cause a whole lot of drama.

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Yep, some celebs picked Halloween outfits that stirred up serious controversy for all the wrong reasons. Wanna see the most jaw-dropping examples of costumes that made people go, "Wait, what were they thinking?!" Buckle up, it’s quite the ride!

#1

Khloe Kardashian’s Pimp Costume… With Leashes?

Khloe Kardashian’s Pimp Costume… With Leashes?

GettyImages , Classic-Carpet7609 Report

Okay, Khloe. A pimp costume is one thing. But adding four black women wearing collars and leashes? That’s not just a costume, that’s a huge "Oh no."

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    #2

    Emily Hampshire & Friend: Johnny Depp And Amber Heard… Oof

    Emily Hampshire & Friend: Johnny Depp And Amber Heard… Oof

    luna1uvgood Report

    Dressing up as real people is one thing, but turning a very public and painful feud into a Halloween joke? Yeah, that’s a hard pass from us.

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    Halloween’s your chance to rock a costume that makes people stop and stare - but in a good way! Whether you’re scaring folks, making them laugh, or just looking darn cute, you want those compliments, not the side-eyes.

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    But beware - the hunt for "cool" can sometimes land you in hot water when your outfit accidentally crosses a line.

    #3

    Oliver Peck's Blackface Superman – Yikes

    Oliver Peck's Blackface Superman – Yikes

    Noonyezz , myspace Report

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    #4

    Jason Aldean’s Lil’ Wayne Blackface Look

    Jason Aldean’s Lil’ Wayne Blackface Look

    Cheesy_DaBad**s Report

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    Sure, you can wear whatever you want. Freedom, baby! But fun doesn’t have to come at someone else’s expense. Some costumes that seem like a funny or clever idea might actually hurt feelings or spread stereotypes without you realizing it.

    So before you commit, maybe think twice about the message your costume sends.

    #5

    Patti Harrison As Michael Jackson With A Baby

    Patti Harrison As Michael Jackson With A Baby

    curttimagurtti Report

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    #6

    Jared Leto Took On The Pope Costume

    Jared Leto Took On The Pope Costume

    Classic-Carpet7609 Report

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    Heads up: Wearing cultural symbols or traditional clothes as costumes? Big no-no. Things like headdresses, kimonos, or anything that turns deep traditions into just a prop can come off as super disrespectful - even if you meant well.

    If you’re wondering "Is this okay?" the answer is usually "Nah, better not."

    #7

    Chrissy Teigen and John Legend... Back in '08

    Chrissy Teigen and John Legend... Back in '08

    frenchsilkywilky , GettyImages Report

    Throwback to Chrissy and John Legend’s costume moment that’s still getting talked about (and maybe regretted?).

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    #8

    O.J. Simpson’s Odd Gynecologist Costume

    O.J. Simpson’s Odd Gynecologist Costume

    I_WORD_GOOD Report

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    One pop culture fave, the Day of the Dead face paint, is actually a rich and sacred tradition honoring loved ones who’ve passed away. Turning that into a quick Halloween look without knowing the meaning? Definitely a miss.

    Respect matters, even in the spookiest of seasons.

    #9

    Hilary Duff & Jason Walsh: Native American & Pilgrim

    Hilary Duff & Jason Walsh: Native American & Pilgrim

    Casamigos Tequila Halloween Party Report

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    #10

    Billie Eilish & Jesse Rutherford’s 2022 Costume Moment

    Billie Eilish & Jesse Rutherford’s 2022 Costume Moment

    melglimmer09 Report

    Billie and Jesse went all out, but the age-gap clowning vibe had people feeling super awkward.

    Fans gave a little grace, but the vibe was definitely off. Cringe alert!

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    Costumes making light of real struggles? Hard pass. Dressing up as a homeless person or refugee? No one’s laughing - it's just plain insensitive. Real people have real pain, and that’s not party fodder.

    #11

    Colten Hayes As Kanye

    Colten Hayes As Kanye

    Classic-Carpet7609 Report

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    #12

    Ellie Goulding’s Native American-Inspired Costume

    Ellie Goulding’s Native American-Inspired Costume

    Background-Oil-2619 , GettyImages Report

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    Also, steer clear of outfits that glorify controversial historical figures or painful events. A little research goes a long way to avoid accidentally stepping on toes.

    #13

    Kate Hudson’s Rajneeshee Movement Costume

    Kate Hudson’s Rajneeshee Movement Costume

    Classic-Carpet7609 Report

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    #14

    Bill Maher As Steve Irwin—Too Soon?

    Bill Maher As Steve Irwin—Too Soon?

    Classic-Carpet7609 Report

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    Bottom line: Halloween should be fun for everyone. You can totally stand out with something clever and cool without hurting anyone’s feelings. So, pick a costume that’s all about good vibes and spooky fun, not messy drama.

    #15

    Luann De Lesseps Channeling Diana Ross... Kind Of

    Luann De Lesseps Channeling Diana Ross... Kind Of

    Classic-Carpet7609 Report

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    #16

    Scott Disick Wearing Traditional Arabian Outfit

    Scott Disick Wearing Traditional Arabian Outfit

    Classic-Carpet7609 Report

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    #17

    Shaun White Dressed As ‘Simple Jack’ From Tropic Thunder

    Shaun White Dressed As ‘Simple Jack’ From Tropic Thunder

    Classic-Carpet7609 , shaunwhite Report

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    #18

    Ashley Benson As Cecil The Lion

    Ashley Benson As Cecil The Lion

    Background-Oil-2619 Report

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    #19

    Ashley Tisdale’s Cultural Appropriation Costume

    Ashley Tisdale’s Cultural Appropriation Costume

    Ashley Tisdale , Ashley Tisdaledale Report

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    #20

    Tia Mowry As A Geisha—Not The Best Idea

    Tia Mowry As A Geisha—Not The Best Idea

    Background-Oil-2619 , tiamowry Report

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