Australian fashion designer Pip Edwards is again at the center of dating chatter after sharing Instagram snaps that appear to show her with a man described as Sydney nightlife bar tycoon Dylan Hales. The pictures were posted from New York, where Edwards was seen riding on the back of a motorcycle driven by Hales and later observed at an outdoor café with him. The posts suggest a developing connection, fueling talk about a new romance amid her social-media updates.
In the spread of images, Edwards, the founder of P.E Nation, wore a sporty ensemble—black bike shorts, a white tank, and Nike runners—while Hales appeared in dark attire during their city excursion. One image captured Edwards with a pair of viper sunglasses as she clung to the back of the motorcycle. A separate shot showed Hales seated at the outdoor table, dressed in black, with Edwards nearby as they walked in the city streets. Later, Edwards posted a photo of herself walking beside Hales, the pair subtly matching in New York-logoed hats. The photo set arrived as fans and observers watched for updates on whether the two are dating.
The spark of romance appeared to begin with a public display of affection that circulated on social media earlier in the day. A photo posted by DJ Milly Gattegno showed Edwards linking arms with Dylan as they walked down a street, a moment that both Edwards and Hales subsequently reshared to their Instagram Stories. The image offered a glimpse of the pair together and fueled speculation about a relationship forming between the fashion designer and the Sydney hospitality magnate, who is known for his role in New York City nightlife.
Dylan Hales is a prominent figure in the hospitality scene, co-owning several venues in New York with Sydney-based associates. The two men behind the ventures—Hales and his partner Ronnie Flynn—launched The Flower Shop in East Village and later expanded to Little Ways on Broadway. They also own Loosie’s, beneath the Moxy Hotel in the Lower East Side, and a sleek late-night jazz bar called Silver Lining Lounge in Bowery. Their business circle has long connected Sydney taste-makers with New York’s nightlife circuit, a context that has drawn additional attention to the New York outing.
The new-development chatter follows Pip Edwards’ recent personal life update. In March, Daily Mail reported that Edwards had parted ways with her ex-boyfriend Joshua Clapp, a figure in the construction sector who runs Steel + Stitch and operates venues in Sydney’s hospitality scene. Clapp is also the ex-partner of Leah Simmons, a well-known fitness personality and the founder behind the workout program KΛΛIΛΛ, adding an additional layer of social overlap to Edwards’ circle. The public discussion around her dating life has often intersected with coverage of her professional brand, including her work with P.E Nation and collaborations that keep her in the fashion and lifestyle spotlight.
Requests for comment from Pip Edwards and Dylan Hales were channelled through Daily Mail staff, but no statement had been provided at the time of publication. The Daily Mail’s coverage notes the timing of the New York trip and the social-media posts that sparked ongoing chatter about a romance. As with similar high-profile celebrity dating stories, confirmation of a relationship would likely come from the individuals involved or their representatives, rather than third-party commentary.
Edwards, known for her design work and public-facing style, has continued to blend her professional profile with her personal life on social platforms. The New York outing underscores how the line between fashion, nightlife culture, and personal life can become entwined in contemporary celebrity coverage. Observers will likely watch for further posts, appearances, or corroborating statements that may confirm or clarify the nature of the connection between Edwards and Hales as they navigate the public eye in the coming weeks.