Since the end of summer, Shawn Mendes has been On The Road Again—literally. The Canadian singer-songwriter kicked off his latest global tour on August 2 at the Sunny Hill Festival in Pristina, Kosovo, marking a celebration of his greatest hits and the 10th anniversary of his debut album, Handwritten. From there, he took the stage in cities across London, Amsterdam, Madrid, Munich, Boston, Toronto, New York, Chicago, Vancouver, and San Francisco before wrapping things up on October 17 at the Hollywood Bowl in Los Angeles. As always, Mendes shines as a solo performer—but this time, there’s another star sharing the spotlight: his wardrobe.

From exclusive custom pieces to handpicked vintage, Mendes’ tour outfits mark a bold evolution in his personal style. When asked about his standout On The Road Again looks, Shawn gave full credit to his stylist, Kristi Kruser, praising her creative partnership and energy, telling us that “Kristi is a dream to work with. For me, over everything, authenticity is the most important thing when working with anyone in any capacity & Kristi always shows up. Before we even get into clothing, I already feel a deep sense of permission to be messy and honest and real and fully myself around her. On top of that, she happens to be incredibly talented and thoughtful. She’s always pushing for a “why” behind the looks and that’s so inspiring for me.”

What’s more, in a subtle yet striking move, many of the outfits pay homage to the cities he’s performing in—featuring designers and craftsmanship rooted in local culture. Kristi shared her thought process behind this decision, explaining that “When you’re styling a musician, it’s ultimately a collaboration—you have to give up a little autonomy and have faith in each other to make it work. This tour, I wanted to reclaim some of that autonomy by injecting more of myself into it—and to have fun with it. I focused on spotlighting local, young, and independent designers to help foster a space of creative unity.”

Below, we break down Shawn Mendes’ best tour fits so far—and the designers, details, and stories behind them.

Mumbai, India

Backstage in Mumbai, Shawn wore wide-leg khaki trousers with white detailing by Indian label Kartik Research, a brand known for its thoughtful approach to traditional craftsmanship. He paired the look with a black sleeveless shirt and dress shoes, striking a sharp silhouette that balanced edge and ease.

Krakow, Poland

The statement accessory in Krakow? A black leather belt with a sculptural, flower-like gold buckle by local designer Zwyrtech—bold but balanced against an otherwise minimalist look.

Budapest, Hungary

For his Budapest performance, Mendes stepped out in a sleek custom all-black ensemble by Hungarian brand Nanushka and custom boots by Canadian brand John Fluevog. The open black vest gave the look a relaxed, deconstructed edge—understated, yet elevated.

Toronto, Canada

Returning home to Toronto, Shawn repped Toronto-born label California Arts in extra-long, wide-leg denim, paired with a tight white tank and black heeled boots. It was laid-back, confident, and unmistakably him.

Cologne, Germany

In Cologne, Shawn embraced a cowboy-meets-Euro vibe in bootcut jeans, a white tee, and a cowboy hat—all grounded by heeled black boots and denim from German brand No Faith Studios. The look was classic with a twist, and right on theme for a city that knows its fashion.

Vienna, Austria

Wearing archival Helmut Lang (Spring/Summer 2003), Mendes brought quiet luxury to the stage in Vienna. A form-fitting ribbed sweater and tailored black pants made for a refined, almost architectural look—no frills, just intention.

Madrid, Spain

On stage in Madrid, Shawn wore wide-leg trousers from Spanish designer Palomo Spain, paired with a custom belt by Artemas Quibble. The pairing was clean, dramatic, and subtly theatrical—a nod to Palomo’s flair for fashion that tells a story.

Lisbon, Portugal

Lisbon saw Shawn in one of his most intricate looks: a black vest by Kristi Kruser, detailed with obsolete Portuguese coin buttons and an 18th-century tapestry appliqué. The piece felt like a relic from another era—paired with a gold-buckled belt and black trousers, it was thoughtful and quietly ornate.

Montreal, Canada

For his Montreal stop, Mendes wore Early Y’s for men by Yohji Yamamoto, for a suave, open jacket moment in a high-energy home-country performance. The outfit was a deviation from the sleeveless looks that defined the tour, while staying stylish in the colder Canada weather.

Chicago, USA

For Chicago, he dug deep into the archives, wearing a vintage 1960s jersey with subtle graphics, paired with relaxed denim. It was an effortlessly cool look, with just the right amount of wear-and-tear to feel lived in.

Los Angeles, USA

In LA, Shawn kept it laid-back and nostalgic in a vintage Willie Nelson tour tee, blue jeans, and a brown cowboy hat. The look felt natural and unfussy—a love letter to classic Americana with a personal twist.