When it came time for FSF to match 2024 Case Study Competition Finalist Ben Callaghan with a mentor, one name rose to the top: Josh Peskowitz. Josh, a celebrated brand and creative director with deep roots in menswear, retail strategy, and editorial storytelling, was a natural fit. Throughout his career, Josh has held influential roles at Bloomingdale's and Moda Operandi, and he currently brings his sharp eye and creative leadership to CXA. Josh is also the co-founder of The Magasin.
The two first connected in May 2024 during senior presentations at SCAD, where Josh was serving as a judge. It was there that he encountered Ben’s standout case study, The Evolution of a Captain, a Stone Island capsule inspired by Canadian hockey history, military tailoring, and sustainable design principles. Their shared focus on functional, emotionally resonant design and product storytelling made their match both organic and impactful.
In this conversation, Josh and Ben reflect on their creative chemistry, what makes a strong collection, and the evolving role of mentorship in fashion today.
Josh: What first drew you to design, and when did you know this was the path you would take professionally?
Ben: I was always interested in clothes, especially sneakers, but when I got online around age 12, the world of fashion opened up to me. Early Instagram influencers posting outfit grids and fit pics got me curious about brands, styling, and design. At 15, I visited a store in my hometown that carried designer labels like Stone Island and Raf Simons. I was enthralled by the product and wanted to learn everything I could. By high school, I knew fashion was the only path for me, so I went to SCAD to study fashion and committed to building a career in the industry.
Josh: When you are designing, what part of the process do you find the most challenging, and what part is the most rewarding?
Ben: Developing a concept is the hardest. I put pressure on myself to create something meaningful, not just more things the world doesn’t need. Editing is also challenging; there are endless possibilities in fabric, silhouette, and details, and making decisions is tough. The most rewarding part is making the clothes, working with my hands, solving problems, and seeing the final garment worn by someone. That feeling is unmatched.
“I want to create pieces that are meaningful and tell a story, not just add more things the world doesn’t need.”
Josh: This is your first year working out of school. What feedback have you received, and how has it shaped your approach?
Ben: Designing for a customer has completely changed how I think. In school, I focused on what I wanted to create. At work, every decision, every color, graphic, silhouette, and fabric is customer-centric and research-driven. Even with my personal projects, I now think about who I’m designing for and what they need.
Josh: What trends in menswear are you paying attention to right now?
Ben: I’ve been fascinated by a wave of young menswear content creators focused on tailored garments and traditional menswear. Their content is entertaining and educational, teaching about fabrics, designers, and details. It has inspired me to explore these silhouettes and hope more people feel comfortable experimenting with them.
Josh: What has this mentorship brought to your journey that school or internships did not provide?
Ben: Perspective. I used to feel pressure that my first job would define my entire career. This mentorship showed me that careers are long, with twists and turns, and opportunities, expected and unexpected, will come. That realization has been comforting and given me trust in my own growth.
“This mentorship gave me perspective, careers are long, with twists and turns, and new opportunities will always come.”
Ben: You’ve worked across editorial, retail, and brand leadership. How have these experiences shaped your creative lens?
Josh: Each role taught me something different. Having that mix of business and creative experience helps me anticipate what the media will gravitate toward, what the customer wants, and how to shape a concept so it lands. Over time, this background pushed me toward entrepreneurship and helped me think more strategically about every project I take on.
Ben: When you review a new collection, what stands out first?
Josh: Fabric and silhouette are everything. Integrity comes from the parts and labor that go into a garment. Quality doesn’t have to mean luxury; it just has to be good. Customers are increasingly looking for that. When I see a collection, I want to feel the craftsmanship immediately.
“Quality doesn’t have to mean luxury; it just has to be good.”
Ben: Who has been your most important mentor, and what did you learn from them?
Josh: I’ve had many mentors, Nick Sullivan at Esquire, Tim Blanks at Style.com, Kevin Harter and David Fisher at Bloomingdale’s. Working under people with strong points of view helped me define my own. They expected excellence but also encouraged me to bring something new to the table. That shaped how I mentor today. I want younger designers to have room to develop their own eye while delivering on expectations.
Ben: What have you taken away from this mentorship that feels different from past collaborations?
Josh: You came in with a defined vision of who you are as a designer. Your senior collection showed maturity, and I knew you had the potential to make an impact. Watching you take a corporate role while also thinking about your long-term path has been rewarding. Mentorship is about guiding without rushing, and you’ve embraced that.
Ben: What is one piece of advice you always share with emerging talent?
Josh: Define what success means to you. Everyone’s version is different, and your strategy should reflect your goals. Surround yourself with the right people who can handle the tasks that pull you away from designing. Partnerships, like a business partner who complements your strengths, can make all the difference. You can’t be everything at once, so build a team that allows you to do what you do best.
“Define what success means to you, then build the team and structure that allows you to focus on what you do best.”
