Footwear

Since the days of The Squire Shop, our shoe collection has always been a focal point at John Simons. Explore our range of Ivy League classics, including suede chukka boots from Astorflex and Original Playboy, iconic penny and beefroll loafers by Rancourt, and robust workwear options from Paraboot, as well as much more. Our collection ensures you’ll step out in 4/4 style, wherever your journey takes you. 

THE DIZZY HANDWOVEN SHIRT

A must have item for your mid-century modern wardrobe, incorporating John’s favourite Ivy League details from the 1950s/1960s.

Of primary importance to many aficionados of the Ivy League look, is the generous collar roll. When fully fastened, the long collar points cascade beautifully, recalling what John describes as “The Ivy League Spearpoint collar”, a feature which would often be found on shirting from the “Jivy Ivy” period in the latter half of the 1960s. When worn open the collar rolls beautifully, a feat which has been achieved by omitting any lining from the collar and placket.   

SHOP HERE

Journal

View all
  • The Original Playboy X Steve McQueen

    The Original Playboy X Steve McQueen

    The story of The Original Playboy shoes began in 1936 when English shoemaker Hutton in Northampton created a completely new shoe with a unique and patented crepe sole construction. The ‘Play-Boy’, as...

    The Original Playboy X Steve McQueen

    The story of The Original Playboy shoes began in 1936 when English shoemaker Hutton in Northampton created a completely new shoe with a unique and patented crepe sole construction. The ‘Play-Boy’, as...

  • Customer Spotlight: Jay Pond-Jones
    • Customer Spotlight

    Customer Spotlight: Jay Pond-Jones

    Jay Pond-Jones has navigated a remarkable and multifaceted career. He began his professional journey training as a Graphic Designer, which led to roles as an Art Director and eventually a...

    • Customer Spotlight

    Customer Spotlight: Jay Pond-Jones

    Jay Pond-Jones has navigated a remarkable and multifaceted career. He began his professional journey training as a Graphic Designer, which led to roles as an Art Director and eventually a...

  • Sebago: A Staple of American Style Since 1946
    • Editorial

    Sebago: A Staple of American Style Since 1946

    Sebago loafers embody a timeless elegance worthy of a chapter in the annals of classic American style. Founded on the shores of Maine in 1946 by New England Natives Daniel...

    • Editorial

    Sebago: A Staple of American Style Since 1946

    Sebago loafers embody a timeless elegance worthy of a chapter in the annals of classic American style. Founded on the shores of Maine in 1946 by New England Natives Daniel...

1 3
View all