Hailee Steinfeld and Fiancé Josh Allen’s Rare Date Night in Italy Will Leave You Starving for More

Watch: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. 

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Hailee Steinfeld and Josh Allen: Romance Rewind

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. 

Ice Spice

At the Roberto Cavalli Spring/Summer 2026 fashion show on Sept. 25.

Hilary Duff & Shailene Woodley

At the Fendi Spring/Summer 2026 fashion show on Sept. 24.

Naomi Watts

At the Fendi Spring/Summer 2026 fashion show on Sept. 24.

Serena Williams

At the Gucci Spring/Summer 2026 fashion show on Sept. 23.

Demi Moore

At the Gucci Spring/Summer 2026 fashion show on Sept. 23.

Saweetie

At the Dhruv Kapoor Spring/Summer 2026 fashion show on Sept. 23.

Shailene Woodley

At the Tod’s Fall/Winter 2025 fashion show on Feb. 28.

Keira Knightley

At the Tod’s Fall/Winter 2025 fashion show on Feb. 28.

Normani

At the Moschino Fall/Winter 2025 fashion show on Feb. 28, carrying Pepperidge Farm’s Milano bag in collaboration with the luxury label.

Kelly Rutherford

At the Roberto Cavalli Fall/Winter 2025 fashion show on Feb. 27.

Hunter Schafer 

At the Prada Fall/Winter 2025 fashion show on Feb. 27. 

Hailee Steinfeld

At the Fendi Fall 2025 fashion show on Feb. 27. 

Sarah Jessica Parker

At the Fendi Fall 2025 fashion show on Feb. 27. 

Ashley Park

At the Fendi Fall 2025 fashion show on Feb. 27. 

Jade Thirlwall

At the Fendi Fall 2025 fashion show on Feb. 27. 

Charli D’Amelio

Heading to the Prada Fall/Winter 2025 fashion show on Feb. 27.

Victoria Monét

At the Diesel Fall/Winter 2025 fashion show on Feb. 26. 

Suni Lee

At the Diesel Fall/Winter 2025 fashion show on Feb. 26. 

Adriana Lima

Walking in the Fendi Fall/Winter 2025 fashion show on Feb. 26.

Sharon Stone

At the Antonio Madras Fall/Winter 2025 fashion show on Feb. 26.

Olivia Palermo

Sipping on a MARTINI cocktail at the Marni Fall 2025 fashion show on Feb. 26.

Naomi Campbell

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

Doechii

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

Amelia Gray

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

Irina Shayk

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

Tyson Beckford

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

Jessica Chastain

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

Yara Shahidi

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

Dev Patel

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

Daisy Edgar Jones

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

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View More Photos From Milan Fashion Week 2025: Celebrity Sightings
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