It’s the midpoint of June and the highly anticipated Men’s Milan Fashion Week is in full force. With the event underway, brands are hinting at the arrival of their star guests, building excitement for what’s to come in the next few days.

In one of those exciting announcements, fashion brand Prada shared pictures of Thai star Win Metawin departing to Milan for their upcoming menswear show. To kickstart this season’s Prada and Win link-up, the actor put a spin on some of the most daring fashion trends: double waistband pants and peeking boxers.

Getting On Board

Win Metawin shared a slew of photos dressed in head-to-toe Prada to announce his attendance at the brand’s Spring Summer 2025 show. The actor posed in a low-cut scoop-neck tank top tastefully styled with a baggy denim jacket. As for accessories, Win carried a classic Prada nylon backpack and sported sleek, glossy square-toe shoes. 

The look’s focal point, however, was the actor’s layering game — he paired dark brown slacks with light blue boxers that peeked out from the pants’ waistline. This double-waistband visual effect gave the illusion that Win’s undergarments were purposely pulled higher or the pants were worn lower to show off the waistband of his undies. 

As the fashionista he’s known to be, Win embraced this risqué trend along with the brown and blue combination — a rising color match thanks to the office-core trend. 

Upon arriving in Milan, the Thai star reprised the peeking boxers look again for a street-style outfit. And yes, we’ve officially added both ensembles to Win’s lookbook of most memorable fashion moments. 

Risqué Business 

Win’s fashion statements align with the exposed underwear trend that has been taking over fashion since 2022. Championed by brands like Miu Miu, Thom Browne, and even Dior Homme, the trend focuses on recontextualizing pieces that would be generally used as undergarments or underlayers as pieces purposely left exposed  

Offering a throwback to the ‘90s sagging pants, the double waistband styling is for the brave and comes in different variations. Stars embracing this cheeky trend include Zendaya, who went sports chic with a shimmering Lacoste outfit and exposed briefs; TWICE’s Momo, who pulled off a preppy take with Miu Miu pieces; PP Krit, who put a bold and sultry twist to a Balenciaga look and SEVENTEEN’s DK, who opted for a hip and urban style with a Diesel look. 

Front Row Anticipation

Now that the actor has fully embraced and rocked the double waistband trend — not only once but twice! — fans and fashion enthusiasts are eagerly anticipating Win’s front-row outfit. 

As a Prada ambassador, the Thai heartthrob has been a consistent presence at Fashion Week since 2022. His stylish appearances generate great anticipation and draw large fan crowds to Fondazione Prada, demonstrating his global popularity and relevance in the fashion industry. In fact, every season Win emerges as one of the top Media Impact Value-earning celebrities at Milan Fashion Week.

Prada’s Spring Summer 2025 Men’s Show will take place on June 16 at 2 p.m. CEST. You can watch the runway on Prada’s official social media channels

Interested in more Men’s Fashion Week updates? Check out the Best Celebrity looks of the season here