Stacy Stewart Smith Men's Windsor Pants Collection

The Duke of Windsor — Edward VIII, the most photographed and imitated man of style in the 20th century — understood something that modern menswear has largely forgotten: that a man’s trousers should move with him, not against him. His signature wide-leg, high-waisted, deeply pleated silhouette offered ease, elegance, and authority in equal measure. Stacy Stewart Smith (he, him) revives that conviction for a new generation.

Explore the collection below and visit our blog for guidance on men’s trouser waistline placement and proper sizing — because fit, as the Duke himself knew, is everything.