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
Men's dress boots are leather boots cut slim enough for tailoring: a dress-shoe toe and sole, with the upper carried above the ankle. The closure is what separates the styles, and it decides how quickly a boot goes on and how it looks under a trouser hem.
Leather Chelsea boots pull on with elastic side gussets and no fastening, the cleanest line under a trouser. For black Chelsea boots, the black suede and leather brogue Chelsea boot pairs a suede shaft with polished leather and brogue trim at the front.
Leather chukka boots lace through a few eyelets and stop at the ankle, the most relaxed dress boot here and the easiest with denim. For a brown chukka, the cognac burnished chukka boot is leather lined, with darker burnishing through the toe and heel.
Jodhpur boots wrap a strap around the ankle and buckle it at the side, a riding-boot shape that sits well with a suit. Both are in aniline leather, black or dark brown, like the black leather Jodhpur boot.
Ankle boots keep a dress-shoe front: the black leather side-zip ankle boot opens with a side zipper for a smooth shaft, and the brown and black croc-embossed cap toe boot laces up behind a stitched toe cap. Want a different colour, leather or toe? Every pair is made to order, so ask about Custom Made.
From suits and the office to dark denim and winter weddings.
With a suit, a slim black boot reads like a dress shoe: Jodhpur and side-zip boots keep the line clean, so the shaft only shows when you sit. See how to wear dress boots with a suit.
Trousers should break lightly over the boot, with enough room at the hem to fall over the shaft without catching; cuffs and cropped hems show the strap, zip or elastic side.
With dark jeans, chinos and flannel, a chukka or Chelsea boot is the easiest choice, and a brogue Chelsea adds texture with a knit and an overcoat. For autumn and winter weddings, the dark brown leather Jodhpur boot suits tweed and earth-toned suits; for black tie, choose a black patent Oxford instead.
A boot has to hold the instep and ankle as well as fit the toe.
Lace, zip or buckle the boot so it holds your instep and ankle without pressing, with only a slight heel lift as you walk. A Chelsea has no fastening, so the shaft and elastic hold it on: it should feel snug as you pull it on, but never pinch across the instep.
Choose from your measurements: measure your feet for length and width, and read foot volume vs shoe width. If your instep is high, contact us with your measurements before ordering; extra width does not necessarily provide the instep room you need. If you're between widths, contact us with your measurements before you order. Every design is offered in US 6 to 15, including half sizes, in D, E, EE or EEE.
The leather decides how dressy a boot looks and how it ages.
Polished aniline leather suits tailoring, as on both Jodhpur boots and the side-zip ankle boot; kept polished, a black boot passes for a dress shoe under a suit.
Suede has a soft nap that looks relaxed; brush it after wear and protect it before wet weather. The brogue Chelsea pairs a suede shaft with polished leather at the front.
Burnishing darkens the toe, edges and heel of the cognac chukka, and croc-embossed panels add texture without exotic skin. Leather alone does not make a boot waterproof; check the stated construction and weather suitability before wearing it in heavy rain. See how different leathers age.
The closure. A Chelsea boot has elastic side panels and pulls on with no laces; a chukka is an ankle boot that laces through a few eyelets. Chelseas look cleaner under a suit, chukkas more relaxed. See Chelsea vs chukka boots.
Yes, if they are slim dress boots: black Chelsea, Jodhpur or side-zip boots in polished leather pass for dress shoes under a trouser hem. See dress boots with suits.
A Jodhpur is an ankle boot with a strap that wraps around the ankle and buckles at the side, a riding-boot shape that sits well with a suit. See Jodhpur vs Chelsea boots.