Celebrity pre-Halloween costumes including Demi Lovato as sexy Pennywise

It’s my favorite time of the year: Halloween costume time! I’m covering four big parties this past weekend. First up, we have Demi Lovato’s party at SBE’s Hyde on Saturday. Demi (above) dressed up as Pennywise. Not just any Pennywise, though – a sexy Pennywise. As much as the concept of a sexy Pennywise makes me bark out in laughter, I have to give it to Demi, her look is good. The makeup and hair are fantastic, and the costume actually stays in the realm of the film version’s fluff and flounce, while still showing leg and cleavage. For a sexy clown, she’s done a great job. Also at Demi’s party was Kate Beckinsale in a nice Breakfast at Tiffany’s send up (pictured with Jonathan Voluck as Elton John):

Travis Barker gets credit for staying on theme in creepy clown makeup. Jameela Jamil dressed as a nun and it looks like the costume was pretty good, but I can’t find a shot to confirm that. Also there was Paris Hilton who went as pioneer astronomer Annie Jump Cannon, nailing both period and detail. Just kidding, she went as a basic sexy schoolgirl and wore sunglasses and fingerless gloves because: why bother, right?

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Paris should have been the lead in since her Electrify perfume promo party kicked things off last Thursday. But there weren’t very many notable looks so we led with Demi, who was at Paris’ party too. Paris wore a sexy, sheer warrior ensemble from Trashy Lingerie that she – no joke – cut the skirt off because I guess it was two demure in its original form:


Demi dressed as Marie Antoinette:

Forgive my historical snobbery but if you feel the need to “sexify” a Marie Antoinette costume, you’ve kind of missed the point. The wig is good, and the bodice is well done, though. And it was a Paris H party so pretty much everyone was dressed as a sexy something. The winner, though, was probably Rich Kids of Beverly Hills’ EJ Johnson, who dressed as Paris Hilton as Boudoir Barbie. Points for creativity. Heidi Klum and new husband Tom Kaulitz were there as well. I guess they went as glitter bombs?

It’s not up to Heidi’s usual standards so I’m hoping it was just a feint to her usual level of halloweenery.

Unicef held a masquerade party at the Kimpton La Peer Hotel on Saturday. Billie Ellish performed. But what her costume was exactly, I don’t know. She wore her usual skater girl look but added a diamond studded, chain mail face mask. I would knock her for phoning it in, but the mouth mask looks incredible when it’s in place:

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I could have worked wonders around that piece. Avril Lavigne was a silver half skeleton, I guess:

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Her blue hair looks great with the silver outfit and the boots are fantastic but I dislike the rest. It was a Masquerade ball and not a costume party so many of those attending stuck to semi-fancy dress and a mask, so not too many pics to show from this one. Nats Getty and Gigi Gorgeous killed it as Jack Skellington and Sally, though:

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Casamigos had a Psychedelic Spirits Themed Party but barely anyone outside hosts Rande Gerber and Cindy Crawford stuck to theme:

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The big story there was Jessica Biel dressed up as N’Sync Justin Timberlake and four friends dressed as the rest of the band while Justin himself dressed as a microphone:

I suppose it was clever, but, well, it’s them. Lisa Rinna dressed as JLo in her infamous Oscars Versace dress:

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That would have been more impressive if JLo hadn’t already done it during the Versace fashion show.

Oh shoot, I almost forgot, Paris Hilton was there too. As a sexy showgirl. The sad part is this was decent costume and she was styled beautifully but predictably killed any enthusiasm I had for it.

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Photo credit: WENN Photos, Avalon, Backgrid and Instagram

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20 Responses to “Celebrity pre-Halloween costumes including Demi Lovato as sexy Pennywise”

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  1. Abby says:

    I think Jessica Biel and JT killed it actually. Made me laugh.

    SO MANY BOOBS. It feels so overdone these days, to be “sexy _____” Having said that, I really liked Demi Lovato’s Marie Antoinette, and actually think Avril’s blue hair looked great.

    Oh and the Jack Skellington/Sally looked amazing!

  2. MariaS says:

    Paris Hilton is so one-note. She has been doing the long, cheap looking blond weave, blue contacts, fake tan, chest pushed forward look for 2 decades. Evolve lady!

  3. snowqueenM says:

    The only one I really like is DL’s Marie Antoinette. I’m not sure what’s so “sexified” about it… 🧐 That’s late 18th century fashion, for the aristocrats anyway. Lots of makeup, very colorful, very low bodices, enormous hair. And Marie Antoinette was a figure that fascinated people… There was a lot of focus, in her lifetime, about her charm, attractiveness and sexuality.

    • Hecate says:

      That’s my point, MA doesn’t require any more sexiness. The top half of the costume is great, I just don’t know why she saw the need to go with lace bloomers instead of some semblance of a skirt, as shown in the second photo of her Instagram. The construction, as a whole, is very well done, though

    • otaku fairy.... says:

      Same. Heidi’s glitter zombie is cool too.

  4. Virginia says:

    Also kind of loving sexy Pennywise!

  5. Virginia says:

    I think Travis Barker did half-ass Joker makeup.

  6. ItReallyIsYouNotMe says:

    I have a friend whose personal style is sexy EVERYTHING so it’s on hyperdrive at Halloween. Sexy Princess Anna one year, sexy pumpkin another, and then this year it was Sexy Hermione. I secretly roll my eyes but have never said anything because 1) it’s not my place and 2) she’s a really good person.

  7. Jadedone says:

    I honestly cant with these “sexified” Halloween costumes. Just be pennywise or Harry Potter, you dont always have to look sexy, it’s just so over done. Dont get me started on sexy school girl costumes.

    • ME says:

      I agree. First of all Halloween costumes are supposed to be “scary” not “sexy”. I don’t understand why being sexy at Halloween is a thing. It’s stupid.

  8. Jessica says:

    Lame. I prefer looking at pets dressed up. I saw a chocolate lab dressed as a s’more. That was awesome! Far more creative than these travesties.

  9. jenner says:

    Paris Hilton basically shows up as herself.

    • My3cents says:

      In the top photo she showed up as vintage 90′s Paris!
      Please can you not tell the difference? (Kidding)

    • amayson1977 says:

      What’s going on with her hands? She’s my age-ish (I’m 42…I just googled and she’s 38) so I can’t imagine that they are that ravaged with age, but she’s been doing the stupid fingerless gloves thing since she pressured that poor idiot into proposing with the giant, tacky doorknob ring in the snow in like 2016. Strange.

  10. shells_bells says:

    OMG Kate & Jonathan have FunYuns in their basket. One of my fave guilty pleasures!!!