Men's Classic Fit Boxer Shorts

Men's classic fit boxer shorts by Derek Rose, cut with a relaxed fit and a tradi...

Men's classic fit boxer shorts by Derek Rose, cut with a relaxed fit and a traditional two-button keyhole fly. In pure silk, cotton, cotton batiste, cotton satin and jacquard — the full range of fabrics, across stripes, checks, prints and plains.

The classic fit sits generously through the seat with a centre back seam, the most traditional boxer short cut we make. Silk styles are designed in our London studio and made in the United Kingdom. Cotton and cotton batiste styles carry the same considered detailing — lighter in weight, easy to wear and beautifully finished throughout.

Read our underwear guide for help choosing between classic and modern fit, or see modern fit boxer shorts for a closer cut.

A relaxed fit with nothing relaxed about the finish.
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Men's Classic Fit BoxersPeople of London Blue Stripe
$100.00
New
Men's Classic Fit BoxersSilk London Toile Black
$255.00
New
Men's Classic Fit BoxersParis Cotton Black Rose
$100.00
Men's Classic Fit BoxersWellington Cotton Satin Multi Stripe
$100.00
Men's Classic Fit BoxersBarker Cotton Teal & Red Check
$100.00
Men's Classic Fit BoxersSilk Navy Blue Rose Print
$255.00
Men's Classic Fit BoxersLondon Scenic Print Multi
$100.00
Men's Classic Fit BoxersAmalfi Cotton Batiste Aqua Blue Stripe
$100.00
Men's Classic Fit BoxersRoyal Cotton Teal & White Stripe
$100.00
Men's Classic Fit BoxersSilk London Geo Cross Blue & Teal
$255.00
Men's Classic Fit BoxersLondon Geo Cross Cotton Batiste Taupe
$100.00
Men's Classic Fit BoxersCotton Batiste Camo Green Rose Print
$100.00
Men's Classic Fit BoxersBarker Cotton French Blue & White Check
$100.00
Men's Classic Fit BoxersCotton Batiste Navy Blue Night Sky Print
$100.00
Men's Classic Fit BoxersCotton Jacquard Navy Blue Camo Rose Weave
$100.00
Men's Classic Fit BoxersSilk Navy Blue & Blue Stripe
$255.00
Men's Classic Fit BoxersCotton Batiste Navy Blue Rose Motif
$100.00
Men's Classic Fit BoxersCotton Batiste Blue Multicolor Diamond Print
$100.00
Men's Classic Fit BoxersCotton Jacquard Navy Rose Star Pattern
$100.00
Men's Classic Fit BoxersGingham Cotton Blue
$100.00
Men's Classic Fit BoxersSavoy Cotton White
$100.00
Men's Classic Fit BoxersAmalfi Cotton Batiste Blue
$100.00
Men's Classic Fit BoxersJames Cotton Blue
$100.00
Men's Classic Fit BoxersCotton Batiste Navy Pin Dot Print
$100.00
Men's Classic Fit BoxersWoburn Silk Satin Navy
$145.00
Available in 2 colours
Men's Classic Fit BoxersWoburn Silk Satin Black
$145.00
Available in 2 colours
Men's Classic Fit BoxersBailey Silk Navy
$230.00
Men's Classic Fit BoxersFelsted 3 Cotton Blue
$100.00
Men's Classic Fit BoxersWellington Cotton Brown and Blue Multicolor Stripe
$100.00