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Men's Chelsea boots

23 pairs
Curator's note

The Chelsea boot is stylish town boot first popularised by Queen Victoria. The key feature is the elasticated sides that allow you to slip the boot on, which was a Victorian invention of huge importance as it moved away from laces or buttons. Elastication reduced the visual bulk of the top of the shoe (vamp) allowing it to have a sleek, elegant appearance.

That cool and sophisticated designer Chelsea boots men’s look has become iconic for many in pop culture and was probably most famously a staple of The Beatles when paired with a Cuban heel.

Men’s Chelsea boots can be dressed up or down. Both suede or leather Chelsea boots give you a huge variety of styling options. If you had to pick just one or two options, we suggest a black or brown leather Chelsea boot for work or weekends and dark brown suede luxury men’s Chelsea boots for relaxed chic. Follow the link for more information about Chelsea boots.

SS · 2026
Product image for Loake Chatsworth (Rubber) in dark brown suede
№ 01
Last Loake Jockey
Chatsworth
Loake · Chelsea Boot · Suede · Rubber sole · Dark Brown Suede
£269.00
Product image for Herring Ipswich II in brown waxy calf
№ 02
Last Santoni
Ipswich II
Herring · Chelsea Boot · Calf Leather · Leather sole · Brown Waxy Calf
£185.00
Product image for Loake Chatsworth (Rubber) in brown waxy calf
№ 03
Last Loake Jockey
Chatsworth
Loake · Chelsea Boot · Calf Leather · Rubber sole · Brown Waxy Calf
£319.00
Product image for Herring Muswell in dark brown calf
№ 04
Last Z460
Muswell
Herring · Chelsea Boot · Calf Leather · Dark Brown Calf
£395.00
Product image for Herring Kirkdale (Rubber) in mahogany grain
№ 05
Last 175
Kirkdale
Herring · Chelsea Boot · Calf Leather · Rubber sole · Mahogany Grain
£425.00
Product image for RM Williams Comfort Craftsman in mid brown calf
№ 06
 
Comfort Craftsman
RM Williams · Chelsea Boot · Calf Leather · Rubber sole · Mid Brown Calf
£450.00
Product image for RM Williams Comfort Craftsman in dark tan calf
№ 07
 
Comfort Craftsman
RM Williams · Chelsea Boot · Calf Leather · Rubber sole · Dark Tan Calf
£425.00
Product image for Herring Matterhorn in dark brown calf
№ 08
Last 13225
Matterhorn
Herring · Chelsea Boot · Calf Leather · Rubber sole · Dark Brown Calf
£185.00
Product image for Wildsmith Model 170 in dark brown suede
№ 09
Last WILD5
Model 170
Wildsmith · Chelsea Boot · Suede · Rubber sole · Dark Brown Suede
£270.00
Product image for Barker Camborne in brown pull up
№ 10
Last Barker 460
Camborne
Barker · Chelsea Boot · Calf Leather · Rubber sole · Brown Pull Up
£235.00
Product image for Herring Coltham in brown waxy calf
№ 11
Last 52F
Coltham
Herring · Chelsea Boot · Calf Leather · Leather sole · Brown Waxy Calf
£299.00
Product image for RM Williams Comfort Craftsman in chestnut calf
№ 12
 
Comfort Craftsman
RM Williams · Chelsea Boot · Calf Leather · Rubber sole · Chestnut Calf
£425.00
Product image for Herring Guards in burgundy polished
№ 13
 
Guards
Herring · Casual Boot · Polished Leather · Rubber sole · Burgundy Polished
£185.00
Product image for RM Williams Comfort Craftsman in caramel calf
№ 14
 
Comfort Craftsman
RM Williams · Chelsea Boot · Calf Leather · Rubber sole · Caramel Calf
£425.00
Product image for Herring Perry mens brogue Chelsea boots in brown calf
№ 15
Last Z160
Perry
Herring · Chelsea Boot · Calf Leather · Leather sole · Brown Calf
£315.00
Product image for Herring Wilson in dark leaf calf
№ 16
Last 11028
Wilson
Herring · Chelsea Boot · Calf Leather · Leather sole · Dark Leaf Calf
£455.00
Product image for Wildsmith Model 170 in tobacco suede
№ 17
Last WILD5
Model 170
Wildsmith · Chelsea Boot · Suede · Rubber sole · Tobacco Suede
£270.00
Product image for Cheaney Godfrey D in plough suede
№ 18
Last Cheaney 125
Godfrey D
Cheaney · Chelsea Boot · Suede · Rubber sole · Plough Suede
£495.00
Product image for Herring Mountbatten mens Chelsea boots in dark brown calf
№ 19
Last Z401
Mountbatten
Herring · Chelsea Boot · Calf Leather · Leather sole · Dark Brown Calf
£299.00
Product image for Herring Muswell mens Chelsea boots in tan calf
№ 20
Last Z460
Muswell
Herring · Chelsea Boot · Calf Leather · Tan Calf
£395.00
Product image for Loake Ducksworth in dark brown waxy calf
№ 21
Last Loake Stream
Ducksworth
Loake · Chelsea Boot · Calf Leather · Rubber sole · Dark Brown Waxy Calf
£235.00
Product image for Herring Shelley mens rubber-soled Chelsea boots in chocolate brown calf
№ 22
 
Shelley
Herring · Chelsea Boot · Suede · Rubber sole · Chocolate Brown Calf
£225.00
Product image for Herring Shelley mens rubber-soled Chelsea boots in brown suede
№ 23
 
Shelley
Herring · Chelsea Boot · Suede · Rubber sole · Brown Suede
£225.00
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