Fashion Forward: Hailee Steinfeld and Josh Allen Dazzle on Date Night in Milan
In a scene straight out of a rom-com, Hailee Steinfeld and her fiancé, NFL quarterback Josh Allen, stepped onto the romantic streets of Milan for a chic date night during Milan Fashion Week 2025. Talk about couple goals, right? The pair was spotted enjoying their time in Italy, a rare public outing for the duo who have kept their romance mostly under wraps. Dressed to the nines, Hailee flaunted her fashion prowess in a fitted leather jacket, a matching scarf, and sleek black pants, topped with chunky gold earrings and her hair slicked back in a chic low bun. Meanwhile, Josh channeled his inner style icon with a coordinated all-black outfit that included joggers and a striking Prada windbreaker.
The couple’s outing wasn’t just limited to a fancy dinner; they were also seen hand-in-hand while shopping earlier that day, basking in the fill of Italian luxury. Hailee opted for a cozy oversized gray overcoat paired with a crisp white shirt for their shopping spree, while Josh, sticking with his monochrome theme, rocked a cozy sweater with trousers—because why not match your style statements?
This romantic adventure comes on the heels of their recent red carpet debut at the NFL Honors in New Orleans last month, proving that these two are ready to share their love story with the world—albeit selectively. As Hailee noted in a recent interview with Who What Wear, maintaining privacy in her relationship creates a sense of specialness in moments that might otherwise get lost in the noise of fame. “When you realize that so much is already out there in every other aspect of your life, you really learn to cherish the little that isn’t,” she expressed, emphasizing the importance of boundaries.
Of course, she hasn’t shied away from sharing the delightful details of their engagement—an elaborate and beautifully orchestrated proposal in Malibu, overflowing with flowers and candles that made it feel “magical.” This thoughtful gesture, ensuring she looked stunning, is something Hailee is all too grateful for.
So, as Milan Fashion Week struts its stuff with big name appearances from the likes of Naomi Campbell and Jessica Chastain, Hailee and Josh remind us all that love—and a killer outfit—are the ultimate accessories for any event. Let’s be real, who wouldn’t want to snag those goals?
Sources: Celebrity Storm Wire and People Magazine, Who What Wear, Vogue
