Britney Spears's son Sean Preston, 21, and blond bombshell girlfriend dress as Pamela Anderson and Tommy Lee for Halloween

Nov 02, 2026 - 11:04
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Britney Spears's son Sean Preston, 21, and blond bombshell girlfriend dress as Pamela Anderson and Tommy Lee for Halloween

Britney Spears's eldest son Sean Preston was spotted with a blonde bombshell while celebrating Halloween on Saturday night. 

The 21-year-old son of the Princess of Pop and his singer girlfriend Rebecca Guigui appeared to have channeled another blonde pop culture icon as part of their couple's costume.

The pair both sported black leather as Sean dressed up as rocker Tommy Lee to his girlfriend's Pamela Anderson. 

The couple was spotted trying to avoid getting drenched in the rainy weather while leaving Dylan Sprouse and Barbara Palvin's annual Halloween bash in North Hollywood. 

Sean's outing comes just weeks after reuniting with his famous mother on a family trip. 

Earlier this month, Spears brought along both of her sons to visit Dollywood, the Tennessee theme park of late singer Dolly Parton, for a family trip. 

Britney Spears' eldest son Sean Preston was spotted with a blonde bombshell while celebrating Halloween on Saturday night

Spears shares sons Sean Preston and Jayden James, 20, with her ex-husband Kevin Federline. 

The pop star, 44, was previously married to the dancer, 48, for just over two years before their late 2006 split, with their divorce being finalized nine months later. 

Sean's Halloween outing also comes amid news that his father is allegedly facing a staggering amount of credit card debt since Spears's child support payments ended.

The Daily Mail previously reported that the former backup dancer was hit with a lawsuit in February when Bank of America sued him for alleged unpaid credit card debt.

Sean seemingly shrugged off the headline-making news as he went out with his girlfriend for Halloween.  

On the same day, Sean's girlfriend posted multiple TikTok videos of them showing off their couple's costume before hitting the town for further festivities.

Sean wore a black leather jacket paired with a white tank top, baggy jeans and sunglasses.

His girlfriend wore a black corset paired with skintight pants and slim, rectangular sunglasses.

Spears' 21-year-old son and his singer girlfriend Rebecca Guigui dressed up as Tommy Lee and Pamela Anderson, respectively

On the same day, Sean's girlfriend posted multiple TikTok videos of them showing off their couple's costume before hitting the town for further festivities. (Source: @rebeccaguigui_ on TikTok)

Sean wore a black, leather jacket paired with a white tank top, baggy jeans and sunglasses. (Source: @rebeccaguigui_ on TikTok)

His girlfriend wore a black corset paired with skintight pants and slim, rectangular sunglasses. (Source: @rebeccaguigui_ on TikTok)

Just two weeks earlier, he was spotted in a rare family photo shared on his pop star mother's Instagram page. 

On October 7, she shared a photo of her two sons standing beside her as they posed in front of a Dollywood sign. 

In the caption of the post, Spears typed out: 'Wow wow!!! I didn't know this place existed, so incredibly cool and exciting… 

'But extremely hot and my skirt is too big for me… family outings!!! DOLLYWOOD IS ABSOLUTELY ADORABLE!!!' 

The Toxic hitmaker also uploaded a separate reel to show a portion of the park that was decked out with colorful decorations. 

Spears additionally filmed a quick selfie video as both she and Jayden waited in line to go on one of the many rides.

The visit to the park comes after singer Dolly Parton passed away at the age of 80 on August 25 following a private battle with cancer. 

The songstress has given fans occasional glimpses on social media as she bonds with her once estranged sons. 

Late last month, Spears shared a sweet tribute to Jayden in celebration of his 20th birthday.

Spears shares sons Sean Preston and Jayden James, 20, with her ex-husband Kevin Federline. (Source: @britneyspears on Instagram)

The pop star, 44, was previously married to the dancer, 48, for just over two years before their late 2006 split, with their divorce being finalized nine months later; pictured in February 2006

Sean's outing comes just weeks after reuniting with his famous mother on a family trip. Earlier this month, Spears brought along both of her sons to visit Dollywood, the Tennessee theme park of late singer Dolly Parton, for a family trip. (Source: @britneyspears on Instagram)

She included a present-day photo of her youngest child as he appeared on stage, as well as an adorable throwback snap when he was younger.

'Happy birthday to my handsome young boy oh dear lord we have this beautiful thing called life in front of us, it's such a beautiful delicate thing. I hope I can be the best mommy in the world every day of ur life!!!!'

On Sean's birthday, she shared three separate posts, including one of him posing in a dapper, white button-down shirt, writing in the caption: 'happy b day baby!'

'Happy early B-day to u as well …. please stop working out so much because your muscles r starting to scare me …. JK! Well I'm so proud of the young man you have become. P.S. This was in London, strolling in the park …. Preston absolutely loved London!!!' 

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