Few Black designers in the West bear the weight and good fortune of continuing their family’s legacy in the business. Charlie Casely-Hayford is one of them. He follows in his father’s footsteps, the late Joe Casely-Hayford, a London tailor whose approach was steeped in heritage and modernity. Joe’s designs had the precision of Savile Row haberdashery and the creativity that has been thriving in London for decades. Having passed away in 2019, his son accepted the British Fashion Council’s posthumous Special Recognition Award on his behalf in 2023, which honored Joe’s cultural contributions to the menswear industry.
Charlie, 38, is the creative director of the Casely-Hayford tailor he and his father established in 2019. (Prior to his involvement, he was a student at the Courtauld Institute of Art studying art history.) He’s dressed the John Legends, David Beckhams, and Benedict Cumberbatches of the world, he’s even gotten the attention of Drake as well. The brand’s runway shows, between the fall seasons of 2014 and 2017, were bold. They were filled with eye-catching color combinations, abstract prints on coats, and clear historical references. “But over time, we’ve become more restrained,” Casely-Hayford explains over a Zoom call.
Indeed, neutral-toned ready-to-wear predominates the label’s offerings, which include handmade and made-to-measure tailoring. But which years of the brand’s history will Charlie draw from in his contribution to the Metropolitan Museum of Art and Costume Insitute’s exhibition “Superfine: Tailoring Black Style”? It’d be great to see a little bit of both: the clothes in the earlier collections were covetable for their fearlessness; today, they attest to Charlie’s appreciation for the subdued.
Below is an edited conversation between ESSENCE and Charlie Casely-Hayford. The conversation spans family and fashion in addition to the significance of the Costume Institute’s forthcoming Spring 2025 exhibition “Superfine: Tailoring Black Style” and a hero jacket made for sipping.
Designers’ work tends to overlap with their home life in some way. Has that been your experience?
[Yes], and I think it’s special because it’s cultural rather than fashion for fashion’s sake. If you can weave in culture in such a natural way that it’s a part of your world, there’s something for people to grab onto or strive for. It goes deeper than the surface level of the transiency.
A lot of contemporary fashion is forced, and I think, “You know, the consumer is not stupid. They can see that there’s no authenticity.” You’re buying into the culture, which is imbued and woven into the tapestry of the clothing. There’s no separation.
I agree.
In our store in London, we make a lot of wedding suits for clients, and it’s wonderful that you are a part of the happiest day of someone’s life. There’s something intangible [about that], something more than the clothing itself.
What can you tell me about the sipping jacket you designed in collaboration with Aberfeldy which is currently a hero item for Casely-Hayford?
The collaboration with Aberfeldy felt natural because both brands share this deep respect for craftsmanship, heritage, and storytelling at the foundation, as a father and son story. And that was an important starting point. In creating the garment, I envisioned something that would reflect the warmth and richness of Aberfeldy whisky while inviting people to savor the moment—even for myself, thinking of my early twenties when I first started working with my dad. It’s about taking time to reflect. This jacket epitomizes embracing and enhancing the moment of sharing.
The British Fashion Council granted your late father the posthumous Special Recognition Award in 2023. How did that feel?
It was an honor to experience it, and [to] receive the award on his behalf.
What’s the significance of the Costume Institute’s forthcoming exhibition for you, as a designer and as a Black man?
Huge. It’s shaped very much by my dad being in the tailoring world and this idea of dressing up and dressing impeccably; everything I saw in terms of the way my dad went about his day-to-day life and the importance and pride he took in his clothing. It’s not just about aesthetics, it’s about the cultural identity behind it.
I hope to see designs [in the show] that delve into the history of Black dandyism from 18th-century abolitionists to the Harlem Renaissance, while also embracing contemporary interpretations. It’s going to open the doors in terms of conversations that haven’t necessarily been had but need to be had.
Which historical figures come to mind when you think of Black dandyism?
When you look at someone like James Baldwin, that’s the kind of dandyism that I gravitate towards, because there are levels of flamboyance in his playfulness. It is slightly more understated, with a beautiful emphasis on tailoring and elements of feminism. I’ve drawn an affinity to his dandyism in terms of my personal style.
What do you make of André Leon Talley’s legacy?
André Leon Talley set the bar. When I think of André, I think of stretching notions of reality and the boundaries in which one can dress. He gave language to a new freedom.
How does your work speak to the themes that might be explored within the Costume Institute’s forthcoming exhibition, or Black dandyism more generally?
I keep using the word flamboyance because there is a flamboyance to dandyism; it’s slightly defined by that. Then I think about my perception of my dad’s work in the early days, even as we began working together—there was a restraint. Whereas you have dandyism as an extreme on one side, [the Casely-Hayford brand] has always approached it through this distillation and restraint. Our house DNA has been defined by that. Our dandyism is more understated than the traditional notions of how people perceive a dandy to be.
Not all Black dandies dress spectacularly.
And there’s a level of vanity that I personally struggle with. I can speak on my father’s behalf and say he would have been the same, and we’ve probably detached ourselves from that extreme. It’s been interesting over the last few months since the initial press release came out. Everyone has gravitated towards that. Hopefully, the exhibition reveals the many layers of the Black dandy over decades and centuries.
