Pip Edwards, 45, was photographed linking arms with Dylan Hale, a Sydney-born bar executive who operates prominently in New York City nightlife, on a street in Sydney on Saturday. The sighting has stirred talk of a new pairing, coming days after Edwards’ public breakup with Joshua Clapp.
An image captured from behind shows the two walking with their backs to the camera, Pip wearing tight black bike shorts and a backless white top, while Hale wore a white tank top that showcased tattoos and a muscular frame as he balanced a young child on his shoulders. The moment quickly circulated on social media after Pip’s DJ friend Milly Gattegno posted the photo on Instagram; both Pip and Hale later reposted it to their Instagram Stories.
The man described as Hale is a co-owner of several high-profile New York venues. He and Sydney-based associate Ronnie Flynn own a string of nightlife spots in the city, including The Flower Shop in East Village and Little Ways on Broadway. They also operate Loosie’s, beneath the Moxy Hotel in the Lower East Side, and Silver Lining Lounge, a late-night jazz bar in Bowery. The groups’ portfolio places Hale at the center of a buzzing New York scene that often intersects with Australian fashion figures who travel for work.
The sighting arrives after Daily Mail reporting in March that Edwards had ended her relationship with Joshua Clapp, who runs the construction firm Steel + Stitch and designs hospitality venues across Sydney. Clapp shares a teenage son named Ryder with Leah Simmons, Edwards’ close friend and the trainer behind the workout program KIΛΛIΛΛ. The connection between Edwards, Clapp and Simmons has been the subject of frequent local chatter in Sydney’s eastern suburbs since the split.
Edwards has a well-documented dating history prior to Clapp. She has previously been linked to Geoff Bainbridge, a businessman known for co-founding Grill’d, a chain of burger restaurants. The two were photographed together in the United States during a business trip connected to Edwards’ fashion label Ksubi. Her relationship with Bainbridge gave way to a subsequent romance with Clapp, but the pair parted ways earlier this year.
In the broader arc of Edwards’ public life, a high-profile chapter involved former Australian cricketer Michael Clarke. The couple’s on-and-off relationship ended in early 2021, and in January 2023, Clarke faced public scrutiny after Jade Yarbrough publicly alleged that he slept with Edwards following their breakup. Those allegations were reported in entertainment circles and covered by multiple outlets at the time.
Requests for comment from Edwards and Hale were directed to their representatives; Daily Mail also sought comment from both parties but did not disclose responses. The latest sighting thus sits within a pattern of Edwards’ high-profile social life continuing to attract attention as she navigates dating chatter alongside her professional commitments in fashion.