Halloween
Hailey Bieber dressed up as four of Britney Spears' most iconic looks and she may have just won Hall...

Hailey Bieber Just Won Halloween With 4 Iconic Britney Costumes

Oops! She did it again... and again, and again.

by Elisa Garcia
Sean Zanni/Getty Images Entertainment/Getty Images

Britney Spears has served iconic looks since her debut in the late ’90s, and each Halloween we see several recreations of Spears’ most famous and memorable looks. And this year is no different. However, Hailey Bieber took the inspo to another level entirely. On Saturday, Oct. 30 Bieber shared multiple Britney-inspired Halloween costumes, and it looks like she just won Halloween. Bieber shared not one, but four Britney costumes that are scary good. The 24-year-old explained the meaning behind her costume choice in her caption, “Happy Halloweekend! the first concert I ever went to was the queen @britneyspears and I’ve been shook ever since.”

You can get a look at all of Bieber’s Britney-inspired looks in her Instagram post. Of course, Bieber showcased Spears’ schoolgirl outfit from the “...Baby One More Time” 1998 music video, the legendary red jumpsuit from the 2000 hit “Oops!...I Did It Again,” Spears’ famous 1999 Rolling Stone cover, and who could forget the unforgettable steamy outfit Spears wore in the 2001 “Slave 4 U” music video. Bieber had a handful of people help her create the iconic looks, from photographer Amber Asaly, hairstylist Clayton Hawkins, stylists Chloe and Chenelle Delgadillo, and loads of others to help with lighting and set design. So, it’s safe to say that this was not a last-minute Halloween idea.

Bieber’s friends were quick to comment on the slideshow of photos, with everyone from Kylie Jenner, Kim Kardashian, Ashley Benson, and Vanessa Hudgens praising the Halloween costume. Given that this year has been a Britney-filled year starting with The New York Times’ Framing Britney Spears doc that highlighted the restraints of Spears’ 13-year conservatorship, which was suspended on September 29, it’s no wonder Bieber decided to pay tribute to the singer.

Spears has been in the industry for over 20 years and we still can’t get enough of these amazing looks and the stories behind them...and it looks like Bieber can’t either.

A 16-year-old Spears broke out onto the scene with her debut hit “...Baby One More Time,” and has since been deemed one of the songs that define the ‘00’s. The director of the hit music video explained that the school setting was all Spears’ idea. “Your initial reaction to this is, ‘I'm being told by a 16-year-old-girl what I should do.’ [But] this girl is 16 and I'm a grown man. Perhaps she has a better perspective on her audience than I do. So I swallowed my pride,” he said. Indeed, it seems Spears knew what she talking about, and showed off her talent in her iconic schoolgirl outfit paired with two pigtails held together with pink fluffy hairbands.

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Spears delivered an equally legendary second album Oops!...I Did It Again with hit songs like “Lucky” and “Stronger,” but the album has become synonymous with the well-known red latex jumpsuit she wore in the video for the title track. The outfit was brought to life by stylist Estee Stanley and costume designer Michael Bush, who completed the look overnight. Yes, you read that right. According to Vogue, Stanley has great memories working with Spears’ on the set and noted how Spears’ wardrobe is often memorable. “People didn’t expect it. She was still young and innocent, and then all of a sudden, she comes out in this vixen-y... skin-tight outfit,” she said. “She definitely knew what she wanted and what she liked—that’s what makes her Britney.”

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One year before Spears was serving looks in space, she was on the May 1999 cover of Rolling Stone. With the cover story being “Inside the Heart and Mind (and Bedroom) of Britney,” the photoshoot entailed a 17-year-old Spears lying on a bed dressed in an intimate sleepwear set with a purple Teletubby in hand. Although some may make the case that the Spears was all too young for such a shoot, the look still defines one of the singer’s most famous eras.

Spears continued to serve looks with her 2001 “I’m a Slave 4 U” music video, which was recorded for her third studio album Britney. The music video showed Spears wearing a pink, bikini-like top with a sleeve of material left to flow as she danced to those iconic lyrics, “I'm a slave for you, I cannot hold it, I cannot control it.” This song actually produced two unforgettable looks with the second one being Spears’ live performance of the song at the 2001 MTV Music Video Awards that featured a yellow python. But I can see why Bieber may have opted out of the latter option.

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Spears has had multiple other iconic looks, but I’d say Bieber did an amazing job executing each of her choices. With Britney being, well Britney, and all the stories from her legendary career, it’s easy to see why people continue to recreate the looks that hold a lot of memory in their hearts.