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Hailee Steinfeld & Fiancé Josh Allen Enjoy Rare Date Night in Italy

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Hailee Steinfeld and her fiancé Josh Allen stepped out for a chic date night while on vacation in Italy during Milan Fashion Week 2025. See their rare public outing. 

By Leah Degrazia Feb 26, 2025 2:22 AM

| Updated 20 minutes ago

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Josh Allen's Sweet Shoutout to Hailee Steinfeld at NFL Honors Proves She's His MVP

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

The "Starving" singer and Buffalo Bills quarterback stepped out for dinner while on vacation in Italy during Milan Fashion Week 2025, and the couple certainly arrived dressed to impress for the haute couture occasion. 

During their Feb. 25 outing, Hailee wore a leather jacket with a matching leather scarf and black pants as she and Josh headed out to the restaurant. To top off her ensemble, the 28-year-old rocked chunky gold earrings and wore her hair in a sleek, low bun. 

As for Josh—who announced his engagement to Hailee in November following over a year of dating—the NFL star coordinated his outfit with the Pitch Perfect alum, opting for an all-black ensemble that included joggers, a plain shirt and a Prada windbreaker. 

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

Earlier that day, they stepped out hand in hand while getting some shopping done in the Italian city. For that excursion, Hailee kept warm in an oversized gray overcoat and white button-down shirt. Meanwhile, Josh, also 28, stuck to his all-black theme, donning a cozy sweater and trousers. 

Hailee and Josh's day out in Milan marked a rare public appearance for the couple, who have kept their romance mostly out of the public eye. In fact, they only just made their red carpet debut last month at the NFL Honors in New Orleans after nearly two years together.

Aissaoui Nacer / BACKGRID

For the Bumblebee actress, ensuring her relationship stays mostly out of the spotlight is about setting important boundaries. 

“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,” Hailee explained to Who What Wear in an interview published Feb. 19. “It just makes things extra special, and it's just for you.” 

Aissaoui Nacer / BACKGRID

But that doesn't mean she stays totally tight-lipped on her love story with the athlete. After all, she was more than happy to share her honest thoughts on Josh's "magical" proposal, which took place in Malibu and included an elaborate display of flowers and candles. 

"I'm so grateful that he did it the way he did so that I looked good,” Hailee gushed. “We have these photos that we'll have and cherish for the rest of our lives that I'm not looking at being like, 'What was I wearing?'"

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

PIERO CRUCIATTI/AFP via Getty Images

Naomi Campbell

Walking in the Dsquared2 Fall/Winter 2025 fashion show on Feb. 25.

Courtesy of Dsquared2

Doechii

Walking in the Dsquared2 Fall/Winter 2025 fashion show on Feb. 25

Courtesy of Dsquared2

Amelia Gray

Walking in the Dsquared2 Fall/Winter 2025 fashion show on Feb. 25

Courtesy of Dsquared2

Irina Shayk

Walking in the Dsquared2 Fall/Winter 2025 fashion show on Feb. 25

Courtesy of Dsquared2

Tyson Beckford

Walking in the Dsquared2 Fall/Winter 2025 fashion show on Feb. 25

Courtesy of Gucci

Jessica Chastain

At the Gucci Fall/Winter 2025 fashion show on Feb. 25.

Courtesy of Gucci

Yara Shahidi

At the Gucci Fall/Winter 2025 fashion show on Feb. 25.

Courtesy of Gucci

Dev Patel

At the Gucci Fall/Winter 2025 fashion show on Feb. 25.

Courtesy of Gucci

Daisy Edgar Jones

At the Gucci Fall/Winter 2025 fashion show on Feb. 25.

Courtesy of Gucci

Julia Garner

At the Gucci Fall/Winter 2025 fashion show on Feb. 25.

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