John Simons

Wool Flannel Ivy Shirt – Blackcurrant Check

£145.00 £99.00

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

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 1960’s. When worn open the collar rolls beautifully, a feat which has been achieved by omitting any lining from the collar and placket.

In addition to the elongated collar points, we have chosen to utilise a seven-button front, inspired by the likes of Gant, Sero and Troy Guild shirt-makers, all of whom introduced 7-button plackets as part of their offerings in the 1960’s. Finally, the shirt’s gradually tapering tails were inspired by yet another, lesser-known shirtmaker of the period, namely, Truval, and their Career Club line.

This particular model is produced in a seasonal flannel-wool fabric. With a soft fluffy nap, the flannel button down is a classic slice of Boom Years Ivy League sportiness! We recommend pairing it with a Silk Knit Tie and Tweed Ivy Jacket for a feast of textured layering which is sure to keep you warm this Autumn/Winter. 


  • 100% flannel wool  
  • 3.5” Collar points
  • 3 Button collar
  • Unlined collar, placket and cuffs
  • 7 button front
  • Gauntlet button
  • Single cuff button
  • Box pleat
  • Locker loop
  • Traditional 1960’s cut with tapered tails
  • Fitting true to size

Pit to Pit:

XS 21″

S 22″

M 23″


XL 25″

XXL 26′

XXXL 27″



XS 15″

S 15.5″

M 16″

L 16.5″

XL 17″

XXL 17.5′

XXXL 18″