Vintage Style Not Vintage Values

Published January 2, 2026 at 12:00 PM EST

a man wearing a straw hat and a fancy suit in front of a graphic — Singer, bandleader, and fashion icon Dandy Wellington has built brands, events, and partnerships by embracing an identity.

Bandleader, style icon, host, and presenter Dandy Wellington strutted his way into Bloomington as part of the Bill Blass Speaker Series put on by the Eskenazi School of Art, Architecture and Design. Wellington embraces the cuts, patterns, and silhouettes of the Harlem Renaissance while making use of social media to get his style and his message out. What is that message? Vintage style, not vintage values. To Wellington, that means admiring the materials, the cuts, the drape, and the timeless fashion of the early 20^th century and leaving a lot of the old-fashioned values where they belong, in the past. We spoke with him about those values, about fashion and how to find your style, and about how to survive in the world of entertainment as a solopreneur.