‘Sleepy Hollow’ Star Sydney Sweeney Shares Sultry Selfies in a Black Bra and Thong, But One Detail Steals the Spotlight
Celebrity-founded brands live or die by how well they’re marketed, and few founders lean into that as hard as Sydney Sweeney. Since launching her lingerie label, she has been its most visible model and its creative engine. Sydney Sweeney’s Syrn selfies have become a regular fixture on fans’ feeds.
The brand launched on January 28 and was quickly positioned as more than a typical celebrity side project. It is backed by Coatue Management, with investors including Jeff Bezos and Lauren Sánchez Bezos, along with Coatue partner Ben Schwerin. The first drop reportedly sold out almost immediately.
Now the latest campaign has fans looking at one small detail. On Sunday, September 27, Syrn posted new mirror selfies of the 29-year-old actress, captioned “Syd selfies, starring the Smooth Cup Demi Bra in After Dark.” She wore the black bra with matching underwear and a dainty gold necklace with pavé diamond “S” and “B” initials, which many outlets read as a nod to her boyfriend, Scooter Braun.
The necklace is the talking point, since neither Sweeney nor the brand has explained it. Fox News noted that the initials match those of Braun, and other outlets reached the same conclusion. It first appeared earlier this month in a campaign for the same bra in a different colorway.
The rest of the styling was simple. Sweeney wore her honey blonde hair in loose waves, with smudged black eyeliner and a deep mauve lip, and shot the images on her phone and a digital camera. The product itself is a smooth-cup design intended to be worn under T-shirts, sharing the fit of the brand’s Romantic Demi bra.
The necklace fits into a larger story. Sweeney and Braun, 45, met in June 2025 at the wedding of Jeff Bezos and Lauren Sánchez in Venice, according to People. Us Weekly reported that they confirmed the relationship in April.
They have become increasingly public since then. They appeared together at the Venice Film Festival on September 4, and on September 24 Sweeney shared final summer photos that included Braun and her friends. Fox News described the couple as increasingly public about a romance they initially kept quiet.
Behind the selfies is a serious business. Syrn is built around four personas: Seductress, Romantic, Playful and Comfy. The Comfy line, which launched on March 4 under the banner “Do What Makes You Naked,” was the last of the debut capsules.
The brand also stands out for its sizing, with 44 sizes ranging from 30B to 42DDD and most pieces priced under $100. Sweeney said her own frustrating experience with a bra that didn’t fit inspired that focus. She also described wanting the brand to reflect the many sides of who her customers are day to day.
Syrn’s marketing has never been shy. The launch campaign included a nighttime shoot near the Hollywood Sign that sparked wide conversation, and some backlash. It was a headline-grabbing approach that echoed the attention around her earlier jeans advertisement.
The brand has also evolved. For the ‘My First Rodeo’ collection in the spring, Sweeney shifted behind the scenes to focus on creative direction, putting other women in front of the camera. Then came a late-summer drop with embroidered details, with early access on September 1. In March, she also filed an additional trademark application for the brand, which hinted at a possible beauty launch.
The current campaign shows why the strategy is effective. Simple mirror selfies feel personal and get shared widely, and a small detail like initials on a necklace turns a product post into a conversation. Fans and entertainment outlets did the rest, from fashion sites to gossip pages.
There is also a business logic behind the lighter tone. Sweeney is known for ‘The Housemaid’ and ‘Euphoria’, and her fame gives Syrn built-in reach. Turning that attention into repeat drops and sold-out collections is the real test for a founder-led brand.
For now, the selfies are doing what they were meant to do. They sell a product, spark chatter about her relationship and keep Syrn in the conversation. Whether the necklace becomes a recurring accessory is something fans will surely be watching.
What caught your attention most in Sydney Sweeney’s latest Syrn selfies?
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