EP207: Crafting Timeless Style with Oldfield Outfitters ft Joe Oldfield

In today’s episode, we’re joined by Simon Parr, a seasoned sales agent and the founder of Heritage Brands Inc.With years of experience representing some of the most iconic names in menswear, Simon brings a wealth of knowledge about the enduring legacy of true heritage brands. We explore what defines a heritage brand, why these companies have remained relevant for decades and in some cases, centuries and how their commitment to craftsmanship, quality, and authenticity continues to shape modern menswear.Simon shares stories from the field, talks about how consumer values have evolved, and explains why these classic brands still hold a powerful place in the menswear industry today. Whether you're passionate about style, curious about brand history, or interested in the business side of menswear, this conversation offers a deep dive into the timeless appeal of heritage menswear.

In this episode, we're joined by Joe Oldfield, co-founder of one of the most quietly compelling menswear brands today, a label rooted in timeless design, subtle craftsmanship, and quality that speaks for itself. Joe shares how his inspiration began close to home, drawing from his grandfather’s style and the understated elegance of 1930s menswear. That influence still runs through the brand’s DNA today a commitment to creating pieces that last, tell a story, and elevate the everyday.We explore his journey to becoming a founder, the values behind his creative process, and how his brand is carving out a distinct place in modern menswear. It’s a rare glimpse into how timeless style is actually made.

In today’s episode, we’re joined by Alessio Monteleone, a true icon in the world of retro classic aesthetics. Alessio has become one of the most recognized and widely talked about creators whose work perfectly captures that nostalgic, vintage vibe we all love. From iconic imagery to timeless design influences, Alessio breaks down what makes the retro classic style so enduring and relevant even today. We explore Alessio’s creative process, the inspiration behind his signature images, and how he brings the past into the present through his art. Whether you’re a vintage enthusiast, a designer, or simply someone fascinated by retro culture, this episode offers a fascinating glimpse into a world where old-school charm meets modern creativity. Get ready to step back in time, appreciate the art of nostalgia, and hear firsthand how Alessio Monteleone has helped shape the conversation around what it means to be truly “retro classic.”

In today’s episode, I’m joined by the brilliant Katy Al-Rubeyi, one of the co-founders of StoryMfG, a brand that's redefining what fashion can and should be. Alongside her partner Saeed, Katy set out to create a label rooted in sustainability, transparency, and craftsmanship long before it became a trend.We dive into the early days of StoryMFG, what sparked their commitment to slow fashion, and how they've grown into one of the most respected names in the industry. From natural dyes to ethical production, Katy shares the values and decisions that shaped the brand's unique journey.Join us for an inspiring conversation about creating with intention, pushing back against fast fashion, and building a brand that truly tells a story.

In today’s episode, we sit down with Kamal Patel, the Sales and Marketing Manager for the legendary menswear brand, Gabicci. Since its founding in 1973, Gabicci has held a defining place in music and youth culture, and Kamal’s journey within the brand is nothing short of remarkable. As a South Asian woman rising to a senior leadership role in a male dominated industry, Kamal’s story is both groundbreaking and deeply inspiring. We explore her path to becoming a key figure in menswear fashion and the first-ever female Chair of The 39 Club, a prestigious collective of menswear agencies and brands appointed in October 2022.Tune in to hear how Kamal broke boundaries, built her career with passion and purpose, and helped shape one of the most iconic menswear labels in British fashion history.

From tuxedos in Harlem nightclubs to tailored suits behind BBC microphones, this episode unpacks the radical legacy of women who wore menswear and made history doing it. From Marlene Dietrich’s Hollywood tux to Gladys Bentley’s jazz swagger, from aviators like Amelia Earhart and Bessie Coleman to Indian royals like Maharani Gayatri Devi and Princess Indira Devi these women didn't just break the rules, they rewrote them. Join me as we explore how women across time, race, and culture used fashion not as costume but as a powerful language of rebellion, identity, and freedom.

In today’s episode, I’m joined by Ian Holdcroft, co-founder of Shackleton Apparel a brand deeply inspired by the legendary Antarctic explorer Sir Ernest Shackleton. We explore the journey behind building a label that’s more than just outerwear it’s a tribute to resilience, courage, and leadership. Ian shares how Shackleton’s incredible legacy influences the brand’s mission, the challenges of launching a purpose-driven company, and what it takes to design gear that’s as bold and enduring as the man it's named after. Whether you're an entrepreneur, explorer, or simply someone in search of inspiration, this conversation will leave you motivated to push your limits.

In today’s solo episode, I dive into the world of Dandism its quiet elegance, its loud rebellion, and the cultural significance often overlooked. Inspired by the recent Met Gala, which sadly felt more like a clash than a celebration, I reflect on how Dandism has historically been a form of resistance, a declaration of identity, and a fight for visibility in the world of menswear. Was this tension at the Gala just fashion drama, or is it something deeper perhaps orchestrated by the fashion elite? Have we lost sight of what these men stood for? Let’s explore the roots, the rebellion, and the beauty of Dandism together.

In today’s episode, I sit down with Ken Sakata, the brilliant mind behind Front Office one of the most captivating names in menswear today. Ken’s journey is nothing short of extraordinary from training as a doctor to becoming a respected voice in fashion through his deeply researched, visually compelling reels that explore the true essence and history of clothing. We dive into how his passion for menswear emerged, the unlikely bridge between understanding the human body and designing garments that fit it with precision, and what he’s learned from both worlds. Ken’s ability to translate complex ideas into powerful, wearable concepts is as inspiring as his story itself. This conversation is a must-listen for anyone curious about the intersection of personal expression, craftsmanship, and the drive to create something meaningful. Ken has not only found his purpose he’s helping others see menswear in a whole new light.

In today’s episode, I sit down with Michael Maccari a visionary whose career has spanned some of the most iconic names in fashion. From serving as Artistic Director at Truth Alone to Creative Director at Perry Ellis, and holding key roles at Armani Exchange, Polo Ralph Lauren, Calvin Klein, and J.Crew, Michael brings decades of experience in menswear design and leadership. We dive deep into what menswear has been, what it’s becoming, and how to balance intense creative demands with personal lifestyle. From the studio to the boardroom, Michael shares how he navigates the pressures of a high level creative role without losing sight of his passion. Join us for a thoughtful, behind-the-scenes look into the evolving world of fashion and the resilience it takes to lead creatively at the top.