Unabashedly Prep‘s Fred Castleberry is one of the subjects. I recently recruited Fred to shoot for The Rake team and he’ll be heading up to Cambridge soon to take photos for my upcoming Andover Shop story.
Fred’s carrying a bag by Lotuff & Clegg, a new leathergoods company based in Massachusetts. Co-founder Joe Lotuff, wearing English bespoke, joined me for lunch last week along with Charlie Davidson, his glamorous ex-showgirl girlfriend (evidently you can be 84 and still have a “girlfriend”), and tennis commentator Bud Collins, known for his fondness for go-to-hell pants, which he got from Charlie decades ago. — CC