The Crown and Climb program is led by Winston “The Dandy Lion” Brathwaite, a seasoned advocate, healer, and legal mind whose life’s work centers on uplifting Black men and boys through healing, clarity, and transformation.

A law school graduate, The Dandy Lion brings over a decade of experience as General Counsel, offering legal insight and principled leadership across complex systems. He began his career as a judicial clerk, grounding him in the discipline of justice and deep listening.

His dedication to service runs deep. As a Disability Advisor for FEMA and ADA authority at the Department of Veterans Affairs, he spent more than ten years fighting for equity, accessibility, and dignity for those often pushed to society’s margins. His work is marked by the honors of a Harry S. Truman Scholarship for Public Service, the Thurgood Marshall Fellowship, and formative service as an AmeriCorps member, where he counseled families affected by domestic violence.

For over 30 years, he has served as a crisis intervention volunteer and has been an ordained priest for 17 years, blending legal, spiritual, and emotional insight with over 25 years of study in indigenous healing methodologies.

More than titles and tenure, The Dandy Lion brings heart. He considers it his sacred calling to walk with Black men—powerful, wounded, brilliant, burdened—as they unearth their truth, reclaim their strength, and define manhood on their own terms.

You are not in the hands of just a teacher. You are in the presence of someone who has lived the work—and is deeply committed to your breakthrough.

A dandy is more than just a man in fancy clothes. Historically, a dandy is someone — usually a man — who carefully crafts their appearance, behavior, and lifestyle as a kind of personal art form. Think of it as stylish rebellion, where elegance, wit, and charm are used to stand out from the crowd, especially in societies where class and race often define your role.

The original dandy, George "Beau" Brummell, rose to fame in early 19th-century England. He didn’t come from royalty or wealth, but by dressing in perfectly tailored suits and acting with confidence and wit, he influenced an entire generation. His look was clean, simple, and sharp — a powerful contrast to the overly decorated clothes of the upper class.

Being a dandy has never just been about clothes — it’s also about attitude. Dandies were often outsiders who used fashion to take control of how the world saw them. As French poet Baudelaire once said, “The dandy creates unity by the strength of his individuality.”

Over time, the dandy became a symbol of rebellion through elegance. Writers like Oscar Wilde and Charles Baudelaire saw the dandy as someone who pushed back against the dullness of modern life by choosing beauty, cleverness, and self-expression over conformity.

What is a Black Dandy?

A Black Dandy is someone who uses style — sharp suits, bold colors, fine accessories — to make a powerful statement about identity, pride, and resistance. But here’s what makes it so special: when a Black person dresses like this, it flips history on its head.

For centuries, Black people were excluded from the social spaces where dandyism was born — elite salons, royal courts, fashion circles. But the Black Dandy takes that same language of style and uses it to reclaim power and rewrite the rules.

Black dandyism is about showing the world that Blackness can be elegant, creative, intellectual, and dignified. As scholar Monica L. Miller writes in her groundbreaking book Slaves to Fashion, being a Black Dandy is:

“An act of performance and defiance… A refusal to be defined by racial stereotypes or economic limitations.”

The Black Dandy isn’t just dressing up — they’re dressing up to speak up.

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