FEATURES: Chiltern Street - London’s Destination for The Rakish Gent

Chiltern Street has always been something of a quiet marvel. Tucked into the elegant enclave of Marylebone, its red-bricked terraces and understated charm have made it a magnet for men of discerning taste. But in recent years, this unassuming street has undergone a remarkable evolution, transforming into London’s definitive destination for contemporary menswear and craftsmanship. As the custodians of this neighbourhood, the Portman Estate has carefully nurtured this transformation, curating a community of independent brands that together make Chiltern Street feel less like a shopping street, and more like an exclusive club for those in the know.

When Freddie Elborne, founder of MONC, set out to establish his first physical store, the choice of location was no accident. “We knew we wanted to be in London, but it could have been anywhere in the city,” he reflects. “What drew us to Chiltern Street was the calibre of independent brands here. It felt like one of London’s best-kept secrets — once you discover it, you come again and again.”

Elborne’s MONC boutique is a sanctuary of sustainable design, offering meticulously crafted eyewear for a clientele as international as it is local. Opened in the wake of the pandemic, MONC initially found its audience in Marylebone’s residents, who quickly became regulars. “After Covid restrictions eased, we saw a beautiful evolution,” says Elborne. “Now our customers are a blend of loyal locals and curious international visitors, particularly from the Gulf countries.”

There’s a genuine sense of community here, one that Elborne values deeply. He points to King & Tuckfield across the street as close friends, and frequents Monocle Café daily not just for coffee, but for camaraderie. “The street has changed,” he notes. “It’s no longer just about menswear; it’s about multifaceted brands that offer so much more.”

For Aidan Keen, store manager at Trunk Clothiers, Chiltern Street isn’t just a location — it’s a village. “There’s an incredible range of boutiques here,” he explains. “From Howarth, where you can pick up a beautiful musical instrument, to Cromford Leather, which feels like part of the street’s very DNA.”

Trunk Clothiers has been a fixture on Chiltern Street for nearly 15 years, a cornerstone of the street’s quiet renaissance. Their clientele, Keen describes, is worldly and quality-driven. “They’re global citizens, not necessarily obsessed with fashion, but they appreciate being well put-together,” he says. “Many of them trust us to curate exceptional brands, so they come not just for the labels, but for our edit.”

Maintaining the intimacy of the in-store experience is paramount for Keen, especially as Chiltern Street grows busier. “The virtual world is expanding, but we make sure our customers feel personally looked after,” he says. In summer, Trunk’s bench becomes a gathering spot, exuding a continental charm. “It’s the kind of place where you can come for coffee, shop for beautiful clothes, enjoy lunch, and a glass of wine,” Keen adds, painting a portrait of leisurely sophistication.

Freddie Briance, CEO of New & Lingwood, echoes this sentiment. For him, Chiltern Street offers a rare refuge from the chaos of the city. “It has a completely different atmosphere from anywhere else,” he says. “Even compared to Marylebone High Street just around the corner, Chiltern Street feels like an oasis.”

New & Lingwood’s storied heritage is a perfect fit for the street. Yet while their legacy may be rooted in British tailoring and academic tradition, Briance is quick to point out the brand’s subtle rebellious streak. “We’re constantly evolving,” he explains. “We reference the past, but our pieces are crafted for today’s customer. That balance keeps us relevant.”

Their clientele is as diverse as their designs, spanning stylish twenty-somethings to distinguished gentlemen in their seventies, all united by a love of craftsmanship and character. “The street naturally draws people who want to enjoy luxury at their own pace,” Briance says. “It’s about purposeful visits and considered choices.”

While the pandemic and the temporary closure of nearby Chiltern Firehouse posed challenges, Briance remains optimistic about the street’s trajectory. “We’re seeing a wonderfully diverse mix of brands here,” he notes. “And I hope it stays that way. Big corporate fashion chains don’t belong on Chiltern Street.”

His personal recommendations? “Shreeji News is an intentional space where you can read the paper, chat with the team, and discover a great new publication. And from a fashion perspective, Sunspel makes incredible everyday basics.”

Charlie Casely-Hayford, founder of Casely-Hayford, shares a similar affection for Chiltern Street. For him, it was always the only choice. “From the moment we considered opening a store, we were adamant it had to be here,” he says. “During the peak of London Collections: Men, there was this incredible buzz, with international buyers and a dynamic group of British menswear designers. Chiltern Street just made perfect sense.”

Today, Casely-Hayford is a hallmark of the street, attracting clients who are both culturally curious and style-savvy. “Our customers want to push the boundaries of their wardrobe,” Casely-Hayford explains. “They want something timeless yet inherently modern.”

Navigating the challenges of independent retail in London, Casely-Hayford has found strength in listening closely to his clientele. “We moved away from seasonal collections to focus on what our clients genuinely want,” he says. “If you can afford anything, then time is your greatest luxury — and we give them that.”

For Casely-Hayford, the future of Chiltern Street is bright, so long as its independent spirit remains intact. “The Portman Estate has done a fantastic job in fostering a community here,” he says. “It’s a place where relationships matter. Our service is personal, and that’s what keeps people coming back.”

This ethos of community and craft is what gives Chiltern Street its unmistakable character. As London continues to evolve, with fast-paced developments and digital retail reshaping the landscape, Chiltern Street stands as a beacon of considered luxury. Here, time slows down. Conversations linger. Transactions feel less like sales and more like relationships being built.

From the polished eyewear ateliers of MONC to the quietly confident curation of Trunk Clothiers, the rebellious heritage of New & Lingwood to the modern classicism of Casely-Hayford, Chiltern Street is a celebration of British style at its most refined and personal. And behind it all, the Portman Estate ensures the street remains true to its ethos: independent, intentional, and impeccably curated.

For the modern gentleman, Chiltern Street is not just a destination — it’s a way of life. Step onto its pavements, and you’ll find yourself part of something enduring, where luxury is defined not by logos, but by love: of craft, of community, and of clothes made to last a lifetime.

Explore further at Portman Marylebone