Hailee Steinfeld and Josh Allen's Stunning Date Night in Italy Steals the Spotlight!

Hailee Steinfeld and Josh Allen didn’t fumble their latest date night.

During Milan Fashion Week 2025, the renowned singer, often referred to as “The Hungry One,” and the quarterback of the Buffalo Bills, took a break from their busy schedules to enjoy a dinner outing while on holiday in Italy. The stylish couple made a fashionable entrance, perfectly dressed for the high-end event.

On their February 25th excursion, Hailee donned a coordinated leather jacket and scarf along with black trousers. She paired this look with substantial gold earrings and styled her hair in a neat, low bun as she and Josh ventured to the restaurant. The 28-year-old completed her stylish attire in this manner.

Speaking about Josh, he revealed his engagement to Hailee in November after more than a year of dating. Notably, the professional football player matched his attire with the actress from Pitch Perfect. He chose an all-black outfit consisting of joggers, a simple shirt, and a Prada windbreaker.

But dinner wasn’t the only adventure the pair went on together since touching down in Europe.

In the Italian city earlier that day, they strolled together with linked arms as they picked up some purchases. For their outing, Hailee stayed warm in a roomy gray coat and white long-sleeved shirt. On the other hand, Josh, who was 28 like her, opted for an all-black attire, sporting a comfy sweater and pants.

Hailee and Josh recently ventured out in Milan as an uncommon display of their relationship, which is typically shrouded from public view. Interestingly, they stepped onto the red carpet for the first time just last month at the NFL Honors event in New Orleans, following almost two years of being a couple.

For the actress who played Bumblebee, maintaining a private relationship is all about establishing crucial limits on public exposure.

Hailee shared with Who What Wear in a recent interview on February 19th that once you understand how much is readily available in many areas of your life, you truly appreciate the small parts that aren’t. It adds an extra touch of uniqueness and exclusivity, making these things even more precious because they are uniquely yours.

However, just because she doesn’t reveal every detail about her love story with the athlete, it doesn’t mean she keeps completely quiet about it. In fact, she was quite open when talking about Josh’s romantic proposal, which unfolded in Malibu and showcased a beautiful arrangement of flowers and candles.

Hailee expressed her gratitude because he handled it in a way that made me shine,” she enthused. “Now, we have pictures that will remain precious to us forever, and I won’t be questioning my outfit in them.

For more star sightings at Milan Fashion Week, keep reading.