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.

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  • Stacy Stewart Smith Men's Dragon & Rhombus Flat Front Cotton Twill Windsor Pants

    Stacy Stewart Smith Men's Dragon & Rhombus Flat Front Cotton Twill Windsor Pants

  • Stacy Stewart Smith Men's Ogee Embroidered Raw Silk Pleated Windsor Pants

    Stacy Stewart Smith Men's Ogee Embroidered Raw Silk Pleated Windsor Pants

  • Stacy Stewart Smith Men's Knit Pleated Windsor Pants

    Stacy Stewart Smith Men's Knit Pleated Windsor Pants

    Stacy Stewart Smith Men's Knit Pleated Windsor Pants

    $875.00
    Sale price  $875.00 Regular price 
  • Stacy Stewart Smith Men's Knit Flat Front Windsor Pants

    Stacy Stewart Smith Men's Knit Flat Front Windsor Pants

    Stacy Stewart Smith Men's Knit Flat Front Windsor Pants

    $695.00
    Sale price  $695.00 Regular price 
  • Stacy Stewart Smith Men's Flat Front Knit Windsor Shorts

    Stacy Stewart Smith Men's Flat Front Knit Windsor Shorts

    Stacy Stewart Smith Men's Flat Front Knit Windsor Shorts

    $595.00
    Sale price  $595.00 Regular price 
  • Stacy Stewart Smith Men's Leather Pleated Windsor Pants

    Stacy Stewart Smith Men's Leather Pleated Windsor Pants

    Stacy Stewart Smith Men's Leather Pleated Windsor Pants

    $1,750.00
    Sale price  $1,750.00 Regular price 
  • Stacy Stewart Smith Men's Suede Pleated Windsor Pants

    Stacy Stewart Smith Men's Suede Pleated Windsor Pants

    Stacy Stewart Smith Men's Suede Pleated Windsor Pants

    $1,200.00
    Sale price  $1,200.00 Regular price 
  • Stacy Stewart Smith Men's Diamond Dodger Tweed Pleated Windsor Pants

    Stacy Stewart Smith Men's Diamond Dodger Tweed Pleated Windsor Pants

    Stacy Stewart Smith Men's Diamond Dodger Tweed Pleated Windsor Pants

    $1,450.00
    Sale price  $1,450.00 Regular price 
  • Stacy Stewart Smith Men's Faux Persian Lamb Pleated Windsor Tuxedo Pants

    Stacy Stewart Smith Men's Faux Persian Lamb Pleated Windsor Tuxedo Pants