Pip Edwards, the Australian fashion designer behind P.E Nation, was photographed in New York on Saturday riding on the back of a motorcycle with a man identified as Dylan Hales, a Sydney hospitality bar owner who runs several nightlife venues. Edwards, 45, posted a series of Instagram snaps from the outing, fueling ongoing speculation about a new romance as she spent time with Hales in the city.
In the photos, Edwards wore black bike shorts, a white tank top and Nike sneakers, while sporting a pair of viper sunglasses in at least one shot as she rode behind the driver. A separate image captured Hales in black attire at an outdoor cafe. Later posts showed the pair walking side by side, subtly coordinated in New York-logo hats, as they explored the city together. The initial flash of interest came when Edwards was seen linking arms with the Sydney man in a photo shared by her DJ friend Milly Gattegno; both Edwards and Hales subsequently reposted the image to their Instagram Stories. In that image, the couple faced away from the camera, with Edwards reaching out to link her arm with Hales.
The man’s tattoos and muscular frame were visible in public shots, and another image from the same social thread showed him carrying a young child on his shoulders while at ease in the company of Edwards. The outing reflects a high-profile pairing that has drawn attention in Australian social circles and across entertainment media.
Dylan Hales is tied to a cluster of New York nightlife venues that have become a fixture in the city’s hospitality scene. He and his Sydney-based friend Ronnie Flynn co-own several venues, including The Flower Shop in East Village, Little Ways on Broadway, Loosie’s beneath the Moxy Hotel in the Lower East Side, and Silver Lining Lounge in Bowery. The duo’s portfolio has helped cement Hales as a prominent figure in the city’s nightlife circuit, with Edwards’s appearance alongside him fueling talk about a potential romance.
The social posts arrive after reports in March that Edwards had ended her relationship with ex-partner Joshua Clapp. Clapp runs the construction firm Steel + Stitch, which designs and operates hospitality venues in Sydney, and he shares a teenage son named Ryder with Leah Simmons, Edwards’s close friend and the founder of the workout program KΛΛIΛΛ. The public-facing nature of Edwards’s social feeds and the visibility of her links with Hales have kept the chatter going among friends and followers.
Daily Mail reporters reached out to Edwards and Hales for comment on the NY outing and the dating reports, but there was no immediate public statement from either party at the time of publication. The couple has not publicly confirmed a relationship, and representatives did not provide additional detail. As the story develops, observers will look for further confirmation or clarification from those involved about the nature of their connection.