Little has changed in the Chelsea boots since their invention in Victorian-era Britain, when they were popular with riders thanks to their elasticated sides. Fast forward to today, the style is still a staple in the discerning gentleman's rotation, and Brunello Cucinelli makes a strong case for it with this pair cobbled from polished leather, including the gusseted panels.

BRUNELLO CUCINELLI Elasticated Side Panel Leather Ankle Boots In Brown
$1175
(30% OFF)
to $1650
set alert
Get extra savings Join Now
Product Details
Shop Across 850+ Stores
Size Guide
Finding the best store options for you…
ModeSens Before You Buy
Don’t miss out! Compare prices across 850+ vetted stores—all in one place. Plus, earn rewards every time you shop.
Join over 2M members today!