EP224: The Final Fitting

In todays episode, we sit down with Carolyn Massey, the pioneering British menswear designer whose thoughtful, detail driven work helped shape the early landscape of London Fashion Week Men's (formerly MAN). As one of the first designers to be featured in this new wave of menswear showcases, Carolyn brought a fresh, intelligent perspective to the industry at a pivotal moment. Carolyn opens up about her multifaceted career, from establishing her own label to working with and designing for major brands. She discusses how these experiences broadened her understanding of craft, production, and the realities of the fashion business. At the heart of our conversation is something deeply important to her: community. We explore how Carolyn worked to build a supportive, inclusive menswear network during a time when the scene was still emerging and why connection and shared vision have always been central to her practice. Join us for an insightful and inspiring discussion about creativity, industry transformation, and the power of community in shaping the future of menswear.

In this episode, we sit down with men’s style creator Henry J Wade to talk about the power of dressing well and how style can shape confidence. Henry opens up about how he first got into men’s fashion, what inspired him to start helping others, and why he decided to challenge himself to style men and show them how confidence begins with presentation. He shares his approach to helping men refine their wardrobes, elevate their presence, and express themselves through timeless, intentional fashion. A conversation about more than clothes  it’s about mindset, self respect, and owning your look.

In this episode, we uncover the inspiring journey of Taylor.A .Jones, an Australian made-to-measure brand grounded in the timeless art of tailoring. Before launching her label, Taylor built a successful career in real estate but she always felt the pull to return to what she truly loved: creating with her hands. Taught to sew and pattern cut by her grandmother, Taylor’s passion for craftsmanship began at a young age. Those early lessons instilled a deep respect for precision, patience, and the beauty of garments made to last. Returning to her roots, she honed her skills in tailoring and pattern cutting, starting with menswear mastering structure, fit, and form before evolving into bespoke womenswear that celebrates individuality, confidence, and modern femininity.Taylor now stands as a symbol of artistry and authenticity, blending traditional tailoring techniques with contemporary design. This episode explores her journey from real estate to the world of made-to-measure fashion, and how a lifelong love of sewing, pattern cutting, and craftsmanship continues to shape her vision of what it means to be truly tailored to perfection.

This Halloween, step inside The Final Fitting. Behind the boarded windows, the scissors are still snipping and the tailor always keeps the appointment !

After taking a much needed break to refocus and recharge, I’m back and in this episode, I’m sharing why stepping away was exactly what I needed. We’ll talk about the pressure of constant creation, the importance of listening to your mind, and how reconnecting with what truly inspires you can reignite your passion. I’ll take you through my week exploring some incredible experiences in London from discovering the soulful storytelling of Rahasya Fragrances to being blown away by the craftsmanship at the Beams Expedition Club exhibition. Each moment reminded me of why menswear means so much more than clothes it’s about history, culture, and emotion stitched into every garment. And we’ll also dive into a major moment for the industry: Grace Wales Bonner’s groundbreaking appointment as the first Black woman to become creative director at Hermès a move that marks a powerful shift in how we see creativity and representation in menswear. This episode is about slowing down, finding purpose, and celebrating the artistry that keeps us inspired.

In this episode, we’re joined by Dan Snyder, the founder and creative mind behind Corridor, the NYC based menswear brand known for its soulful aesthetic and meticulous craftsmanship.Dan shares his journey from working in government to launching a clothing line that’s become a cult favorite for those who appreciate intentional design. We explore how his creative process has matured over the years and how spirituality and personal growth have increasingly become part of his work. Whether you’re a design enthusiast, an aspiring founder, or someone interested in the deeper connection between creativity and consciousness, this conversation offers insight into what it means to build something meaningful  and stay true to yourself along the way.

In this episode, I sit down with Matthew Drinkwater, a leading expert at the intersection of fashion and technology, to explore how artificial intelligence and digital innovation are reshaping the fashion world- menswear. From virtual design studios to predictive trend forecasting, the digital world is becoming more intelligent and more influentialthan ever before. But how does this revolution play out in a specific sector like menswear? Matthew breaks down the unique ways AI is being integrated into the menswear industry, from personalization and fit technology to digital tailoring and consumer engagement. Whether you're a designer, a tech enthusiast, or just curious about where fashion is headed, this conversation offers insight into how technology is not just supporting but transforming creative expression in menswear and beyond. This Episode is not to be missed!

Today’s episode is one I’ve been really excited to dig into. We’re talking about artificial intelligence in menswear how it’s changing everything from personal styling and virtual fittings to how brands design and market their collections. But with all this innovation, I’m asking the big question: What happens to craftsmanship? Can AI and tradition coexist, or are we watching the slow fade of the human touch in fashion? Join me as we explore real world examples, reflect on what’s at stake, and imagine what the future of menswear might actually look like.Next week we are back with a guest who will be talking about Ai and menswear.

For my very first podcast episode recorded in Japan I’m honoured to be joined by Kousuke Suda, one of the co-founders of the iconic menswear brand Kamakura Shirts, also known as Kamakura Classic. From their roots in Kamakura to a global reputation for craftsmanship, the brand has become a symbol of timeless Japanese style, blending precision tailoring with deep influences from Jazz culture and Ivy League fashion.We explore how Kamakura Shirts captures the spirit of 1960s Americana while staying grounded in Japanese tradition and how music, culture, and classic menswear come together in every detail of their design. Kousuke shares the story behind the brand, what Ivy Style means in a modern context, and why Jazz continues to inspire their aesthetic. As I start this episode journey from Japan, it’s the perfect conversation to set the tone personal, stylish, and rooted in culture. If you’re into Japanese menswear, heritage brands, Jazz-inspired style, or just curious about the intersection of tradition and modernity, this episode is for you.

What does it take to build a brand that’s more than just a label  one that becomes a lifestyle, a culture, and a community?In this episode, we sit down with Padraig Whelehan, founder of Brotherwolf, an iconic Australian brand known for its bold identity, raw authenticity, and unfiltered approach to craftsmanship and culture. From the spark of an idea to the creation of a brand that now resonates deeply with people across the country, Padraig shares his journey the challenges, the evolution, and the moments that defined Brotherwolf. We dive into the early days, the inspiration behind the name, what it means to lead with purpose, and how staying grounded in values helped Brotherwolf carve out its own lane in a crowded market.Whether you're a creative entrepreneur, a fan of hard working brands, or just love hearing the real stories behind real people doing big things  this one’s for you.