Dress boots are leather boots with a slim, refined profile made to wear with tailoring: Chelsea boots pull on with elastic sides, chukkas lace through a few eyelets and Jodhpurs buckle a strap around the ankle. Hand-welted and made to order in your US size (6–15) and width (D–EEE), or to your own foot measurements at no extra cost. $299, made in 7–10 working days before dispatch, with a free remake if they don’t fit under our Fit Promise.
Choose a design, then select its offered color, US size and width on the product page.
Browse the current designs below — standard pairs are made to order, with limited batches clearly marked where applicable.
Showing 6 designs
Still unsure about fit? Compare our five lasts → or use the Foot Shape & Last Guide
Chelsea boots pull on with elastic side panels. Chukka boots lace through two or three eyelets and sit at the ankle. Both are easy dress boots for men to wear with denim and chinos.
Jodhpur boots fasten with a strap and buckle that wraps the ankle, a riding-boot shape that works well with tailoring. Side-zip ankle boots give a clean line under trousers.
All are leather dress boots with a slim profile, so they wear like dress shoes with more coverage for cooler months. Need a size, width or color you don't see? Ask about Custom Made.
Chelsea boots, chukka boots, Jodhpur boots and ankle boots.
Chelsea and side-zip ankle boots are the easiest to get on and off and sit cleanly under trousers. The cognac chukka boot suits smart-casual outfits and denim. Jodhpur boots in black and dark brown are the choice when you want something less common with a suit, and the croc-embossed cap toe ankle boot adds texture.
A boot has to fit at the forefoot, the instep and the ankle.
A size that works in a low shoe may feel different in a boot. If your instep is high, choose a wider width (E, EE or EEE) before a longer size, and expect a pull-on boot to feel snug over the instep at first. Every pair is made in US sizes 6 to 15, including half sizes.
Smooth leather for the office, suede and burnished for casual.
Smooth leather boots polish up for the office. Suede and burnished finishes are more casual. Leather boots are not waterproof, so check each pair's sole and care notes before wearing them in heavy rain. Each pair's leather, sole and construction are listed on its product page.