get $30 off sitewide
get $25 off sitewide
free shipping on any order
EXPIRES: 2026-12-31
Summer Box:Up to 40% Off
get $25 off sitewide
get Up to 40% Off On Sale
get $25 off on all orders
6-Month Gift Subscription Now $460
EXPIRES: 2026-12-31
get $20 off your order
Monthly Gift Subscription Now $85
EXPIRES: 2026-12-31
get $20 off your order
Winston Basics Box Now $65
EXPIRES: 2026-12-31
Buy 2 - 3 Items Each Month Just For $75
Stylists Pack Your Box With Care
EXPIRES: 2026-12-31
get $30 off sitewide
get $25 off sitewide
get $25 off sitewide
get Up to 40% Off On Sale
get $25 off on all orders
get $20 off your order
get $20 off your order
free shipping on any order
EXPIRES: 2026-12-31
Summer Box:Up to 40% Off
6-Month Gift Subscription Now $460
EXPIRES: 2026-12-31
Monthly Gift Subscription Now $85
EXPIRES: 2026-12-31
Winston Basics Box Now $65
EXPIRES: 2026-12-31
Buy 2 - 3 Items Each Month Just For $75
Stylists Pack Your Box With Care
EXPIRES: 2026-12-31
The Winston Box is a monthly subscription service catering exclusively to the plus size, or big and tall man. Every month we send a box of 2-3 items right to your doorstep based on the size, style and color preferences you provide.