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Chelsea Boots for the Winter

611 Items
Sorel women brex chelsea boot in Spice/Black - size 9
$102.51
Sorel women brex chelsea boot in Spice/Black - size 9
at: Bonanza
Teva women's midform chelsea water-resistant boots in BLACK - size 5
$67.72
Teva women's midform chelsea water-resistant boots in BLACK - size 5
at: Bonanza
Birkenstock unisex bend chelsea boot in Taupe Suede
$106.40
Birkenstock unisex bend chelsea boot in Taupe Suede
at: Bonanza
Base London Mens Douglas Grain Chelsea Boots - Black
$112.00
Base London Mens Douglas Grain Chelsea Boots - Black
at: Evolve Menswear
Slip-on Chelsea Boots - RELIF40033 / 326 280
$67.00
Slip-on Chelsea Boots - RELIF40033 / 326 280
at: Pavers
Slip-on Chelsea Boots - RELIF40033 / 326 280
$67.00
Slip-on Chelsea Boots - RELIF40033 / 326 280
at: Pavers
Barbour - Women's Brown Birch Chelsea Boots - Size US: 9/ UK: 7/ EU: 40
$196.00
Barbour - Women's Brown Birch Chelsea Boots - Size US: 9/ UK: 7/ EU: 40
at: Jones Bootmaker
Barbour - Women's Black Birch Chelsea Boots - Size US: 8/ UK: 6/ EU: 39
$196.00
Barbour - Women's Black Birch Chelsea Boots - Size US: 8/ UK: 6/ EU: 39
at: Jones Bootmaker
Pendleton heritage park chelsea boot in Black - size 5
$73.36
Pendleton heritage park chelsea boot in Black - size 5
at: Bonanza
Fly London EXIA123FLY Oil Suede Women's Chelsea Boots  - Colour: Taupe
$134.00
Fly London EXIA123FLY Oil Suede Women's Chelsea Boots - Colour: Taupe
at: Legend Footwear
Fly London EXIA123FLY Oil Suede Women's Chelsea Boots  - Colour: Aspen
$134.00
Fly London EXIA123FLY Oil Suede Women's Chelsea Boots - Colour: Aspen
at: Legend Footwear
Gabor - Women's Black Chunky Chelsea Boots - Size US: 8.5/ UK: 6.5/ EU: 39.5
$169.00
Gabor - Women's Black Chunky Chelsea Boots - Size US: 8.5/ UK: 6.5/ EU: 39.5
at: Jones Bootmaker
Jones Bootmaker - Men's Burgundy Polished Chigwell Leather Chelsea Boots - Size US: 10.5/ UK: 10/ EU: 44
$243.00
Jones Bootmaker - Men's Burgundy Polished Chigwell Leather Chelsea Boots - Size US: 10.5/ UK: 10/ EU: 44
at: Jones Bootmaker
Jones Bootmaker - Women's Black Majorie Chelsea Boots - Size US: 8/ UK: 6/ EU: 39
$134.00
Jones Bootmaker - Women's Black Majorie Chelsea Boots - Size US: 8/ UK: 6/ EU: 39
at: Jones Bootmaker
Jones Bootmaker - Women's Black Leopard Majorie Chelsea Boots - Size US: 10/ UK: 8/ EU: 41
$134.00
Jones Bootmaker - Women's Black Leopard Majorie Chelsea Boots - Size US: 10/ UK: 8/ EU: 41
at: Jones Bootmaker
Jones Bootmaker - Women's Brown Majorie Chelsea Boots - Size US: 10/ UK: 8/ EU: 41
$134.00
Jones Bootmaker - Women's Brown Majorie Chelsea Boots - Size US: 10/ UK: 8/ EU: 41
at: Jones Bootmaker
Jones Bootmaker - Men's Chestnut Deakin Chelsea Boots - Size US: 5.5/ UK: 5/ EU: 39
$162.00
Jones Bootmaker - Men's Chestnut Deakin Chelsea Boots - Size US: 5.5/ UK: 5/ EU: 39
at: Jones Bootmaker
Customize Comfortable Black Slip On Elastic Panel Real Leather Men Chelsea Boots
$127.39
Customize Comfortable Black Slip On Elastic Panel Real Leather Men Chelsea Boots
at: Bonanza
Ecco Sculpted LX 55 Full Grain Leather Women's Chelsea Boots  - Colour: Black
$157.00
Ecco Sculpted LX 55 Full Grain Leather Women's Chelsea Boots - Colour: Black
at: Legend Footwear
Fly London Salv Leather Women's Chelsea Boots  - Colour: Taupe
$132.00
Fly London Salv Leather Women's Chelsea Boots - Colour: Taupe
at: Legend Footwear
Fly London Meme030Fly Rug Leather Women's Chelsea Boots  - Colour: Red Red
$134.00
Fly London Meme030Fly Rug Leather Women's Chelsea Boots - Colour: Red Red
at: Legend Footwear
Fly London Meme030Fly Rug Leather Women's Chelsea Boots  - Colour: Dark Brown Green
$134.00
Fly London Meme030Fly Rug Leather Women's Chelsea Boots - Colour: Dark Brown Green
at: Legend Footwear
Fly London Meme030Fly Rug Leather Women's Chelsea Boots  - Colour: Camel
$132.00
Fly London Meme030Fly Rug Leather Women's Chelsea Boots - Colour: Camel
at: Legend Footwear
Fly London Meme030Fly Rug Leather Women's Chelsea Boots  - Colour: Diesel
$132.00
Fly London Meme030Fly Rug Leather Women's Chelsea Boots - Colour: Diesel
at: Legend Footwear
Fly London Meme030Fly Rug Leather Women's Chelsea Boots  - Colour: Black Brick
$134.00
Fly London Meme030Fly Rug Leather Women's Chelsea Boots - Colour: Black Brick
at: Legend Footwear
La Coqueta Kids -  Gold & Tan Leather Girl Chelsea Boots  - EU UK 8 / US 9 / EU 25
$105.00
La Coqueta Kids - Gold & Tan Leather Girl Chelsea Boots - EU UK 8 / US 9 / EU 25
at: La Coqueta
La Coqueta Kids -  Navy Leather Chelsea Boots  - EU 1 UK / 2 US / EU 33
$105.00
La Coqueta Kids - Navy Leather Chelsea Boots - EU 1 UK / 2 US / EU 33
at: La Coqueta
Jones Bootmaker - Men's Dark Brown Suede Cheltenham Handmade Chelsea Boots - Size US: 6.5/ UK: 6/ EU: 40
$243.00
Jones Bootmaker - Men's Dark Brown Suede Cheltenham Handmade Chelsea Boots - Size US: 6.5/ UK: 6/ EU: 40
at: Jones Bootmaker
Jones Bootmaker - Men's British Tan Cheltenham Handmade Chelsea Boots - Size US: 10.5/ UK: 10/ EU: 44
$243.00
Jones Bootmaker - Men's British Tan Cheltenham Handmade Chelsea Boots - Size US: 10.5/ UK: 10/ EU: 44
at: Jones Bootmaker
Jones Bootmaker - Men's Tobacco Suede Cheltenham Handmade Chelsea Boots - Size US: 10.5/ UK: 10/ EU: 44
$243.00
Jones Bootmaker - Men's Tobacco Suede Cheltenham Handmade Chelsea Boots - Size US: 10.5/ UK: 10/ EU: 44
at: Jones Bootmaker
Jones Bootmaker - Men's Taupe Suede Cheltenham Handmade Chelsea Boots - Size US: 9.5/ UK: 9/ EU: 43
$243.00
Jones Bootmaker - Men's Taupe Suede Cheltenham Handmade Chelsea Boots - Size US: 9.5/ UK: 9/ EU: 43
at: Jones Bootmaker
Jones Bootmaker - Men's Dark Brown Cheltenham Handmade Chelsea Boots - Size US: 9.5/ UK: 9/ EU: 43
$243.00
Jones Bootmaker - Men's Dark Brown Cheltenham Handmade Chelsea Boots - Size US: 9.5/ UK: 9/ EU: 43
at: Jones Bootmaker
Fly London MULK159FLY Oil Suede Women's Chelsea Boots  - Colour: Black
$115.00
Fly London MULK159FLY Oil Suede Women's Chelsea Boots - Colour: Black
at: Legend Footwear
Fly London MULK159FLY Oil Suede Women's Chelsea Boots  - Colour: Aspen
$115.00
Fly London MULK159FLY Oil Suede Women's Chelsea Boots - Colour: Aspen
at: Legend Footwear
Fly London MULK159FLY Oil Suede Women's Chelsea Boots  - Colour: Taupe
$114.00
Fly London MULK159FLY Oil Suede Women's Chelsea Boots - Colour: Taupe
at: Legend Footwear
Fly London MULK159FLY Oil Suede Women's Chelsea Boots  - Colour: Pine
$115.00
Fly London MULK159FLY Oil Suede Women's Chelsea Boots - Colour: Pine
at: Legend Footwear
Fly London MULK159FLY Dublin Leather Women's Chelsea Boots  - Colour: Black
$123.00
Fly London MULK159FLY Dublin Leather Women's Chelsea Boots - Colour: Black
at: Legend Footwear
Fly London MEME030FLY Valley Leather Women's Chelsea Boots  - Colour: Dark Gold
$132.00
Fly London MEME030FLY Valley Leather Women's Chelsea Boots - Colour: Dark Gold
at: Legend Footwear
Fly London Medi789Fly Rug Leather Women's Chelsea Boots  - Colour: Mid Brown
$143.00
Fly London Medi789Fly Rug Leather Women's Chelsea Boots - Colour: Mid Brown
at: Legend Footwear
Fly London Medi789Fly Rug Leather Women's Chelsea Boots  - Colour: Petrol
$143.00
Fly London Medi789Fly Rug Leather Women's Chelsea Boots - Colour: Petrol
at: Legend Footwear
Fly London EXIA123FLY Rug Leather Women's Chelsea Boots  - Colour: Petrol
$143.00
Fly London EXIA123FLY Rug Leather Women's Chelsea Boots - Colour: Petrol
at: Legend Footwear
Fly London EXIA123FLY Rug Leather Women's Chelsea Boots  - Colour: Red
$143.00
Fly London EXIA123FLY Rug Leather Women's Chelsea Boots - Colour: Red
at: Legend Footwear
Fly London EXIA123FLY Rug Leather Women's Chelsea Boots  - Colour: Black
$143.00
Fly London EXIA123FLY Rug Leather Women's Chelsea Boots - Colour: Black
at: Legend Footwear
Block-Heeled Chelsea Boots - SENBO40011 / 326 374
$54.00
Block-Heeled Chelsea Boots - SENBO40011 / 326 374
at: Pavers
Sean Chelsea Boot
$175.00
Sean Chelsea Boot
at: Walk London
Jones Bootmaker - Men's Tan Nubuck Debden Leather Chelsea Boots - Size US: 10.5/ UK: 10/ EU: 44
$162.00
Jones Bootmaker - Men's Tan Nubuck Debden Leather Chelsea Boots - Size US: 10.5/ UK: 10/ EU: 44
at: Jones Bootmaker
Jones Bootmaker - Men's Brown Nubuck Debden Leather Chelsea Boots - Size US: 7.5/ UK: 7/ EU: 41
$162.00
Jones Bootmaker - Men's Brown Nubuck Debden Leather Chelsea Boots - Size US: 7.5/ UK: 7/ EU: 41
at: Jones Bootmaker
Jones Bootmaker - Men's Brown Grain Debden Leather Chelsea Boots - Size US: 12.5/ UK: 12/ EU: 46
$162.00
Jones Bootmaker - Men's Brown Grain Debden Leather Chelsea Boots - Size US: 12.5/ UK: 12/ EU: 46
at: Jones Bootmaker
Jones Bootmaker - Men's Black Nubuck Debden Leather Chelsea Boots - Size US: 12.5/ UK: 12/ EU: 46
$162.00
Jones Bootmaker - Men's Black Nubuck Debden Leather Chelsea Boots - Size US: 12.5/ UK: 12/ EU: 46
at: Jones Bootmaker
Jones Bootmaker - Men's Black Grain Debden Leather Chelsea Boots - Size US: 5.5/ UK: 5/ EU: 39
$162.00
Jones Bootmaker - Men's Black Grain Debden Leather Chelsea Boots - Size US: 5.5/ UK: 5/ EU: 39
at: Jones Bootmaker
Dr. Martens Spence Sendal Leather Women's Chelsea Boots  - Colour: Black
$205.00
Dr. Martens Spence Sendal Leather Women's Chelsea Boots - Colour: Black
at: Legend Footwear
Timberland Larchmont Leather Men's Chelsea Boots  - Colour: Jet Black
$196.00
Timberland Larchmont Leather Men's Chelsea Boots - Colour: Jet Black
at: Legend Footwear
Dana Tall Chelsea Boot
$225.00
Dana Tall Chelsea Boot
at: Walk London
Jones Bootmaker - Men's Walnut Chigwell Leather Chelsea Boots - Size US: 12.5/ UK: 12/ EU: 46
$243.00
Jones Bootmaker - Men's Walnut Chigwell Leather Chelsea Boots - Size US: 12.5/ UK: 12/ EU: 46
at: Jones Bootmaker
Barbour - Women's Tobacco Matilde Leather Chelsea Boots - Size US: 5/ UK: 3/ EU: 36
$174.00
Barbour - Women's Tobacco Matilde Leather Chelsea Boots - Size US: 5/ UK: 3/ EU: 36
at: Jones Bootmaker
Barbour - Women's Black Matilde Leather Chelsea Boots - Size US: 5/ UK: 3/ EU: 36
$174.00
Barbour - Women's Black Matilde Leather Chelsea Boots - Size US: 5/ UK: 3/ EU: 36
at: Jones Bootmaker
Gabor - Women's Cognac Babel Leather Suede Chelsea Boots - Size US: 8/ UK: 6/ EU: 39
$134.00
Gabor - Women's Cognac Babel Leather Suede Chelsea Boots - Size US: 8/ UK: 6/ EU: 39
at: Jones Bootmaker
Jones Bootmaker - Women's Black Leather Trieste Chunky Leather Chelsea Boots - Size US: 9/ UK: 7/ EU: 40
$162.00
Jones Bootmaker - Women's Black Leather Trieste Chunky Leather Chelsea Boots - Size US: 9/ UK: 7/ EU: 40
at: Jones Bootmaker
Jones Bootmaker - Men's Sand Suede Deakin Leather Chelsea Boot - Size US: 12.5/ UK: 12/ EU: 46
$134.00
Jones Bootmaker - Men's Sand Suede Deakin Leather Chelsea Boot - Size US: 12.5/ UK: 12/ EU: 46
at: Jones Bootmaker
Jones Bootmaker - Men's Tan Suede Deakin Chelsea Boots - Size US: 6.5/ UK: 6/ EU: 40
$162.00
Jones Bootmaker - Men's Tan Suede Deakin Chelsea Boots - Size US: 6.5/ UK: 6/ EU: 40
at: Jones Bootmaker
Jones Bootmaker - Men's Olive Suede Deakin Chelsea Boots - Size US: 10.5/ UK: 10/ EU: 44
$162.00
Jones Bootmaker - Men's Olive Suede Deakin Chelsea Boots - Size US: 10.5/ UK: 10/ EU: 44
at: Jones Bootmaker
Jones Bootmaker - Men's Chestnut Deakin Chelsea Boots - Size US: 11.5/ UK: 11/ EU: 45
$162.00
Jones Bootmaker - Men's Chestnut Deakin Chelsea Boots - Size US: 11.5/ UK: 11/ EU: 45
at: Jones Bootmaker
Jones Bootmaker - Men's Brown Suede Deakin Chelsea Boots - Size US: 7.5/ UK: 7/ EU: 41
$162.00
Jones Bootmaker - Men's Brown Suede Deakin Chelsea Boots - Size US: 7.5/ UK: 7/ EU: 41
at: Jones Bootmaker
Jones Bootmaker - Men's Black Deakin Chelsea Boots - Size US: 10.5/ UK: 10/ EU: 44
$162.00
Jones Bootmaker - Men's Black Deakin Chelsea Boots - Size US: 10.5/ UK: 10/ EU: 44
at: Jones Bootmaker
Ecco Metropole London Leather Men's Chelsea Boots  - Colour: Black
$157.00
Ecco Metropole London Leather Men's Chelsea Boots - Colour: Black
at: Legend Footwear
JONES 24-7 - Men's Burgundy Gibson Leather Chelsea Boots - Size US: 12.5/ UK: 12/ EU: 46
$189.00
JONES 24-7 - Men's Burgundy Gibson Leather Chelsea Boots - Size US: 12.5/ UK: 12/ EU: 46
at: Jones Bootmaker
JONES 24-7 - Men's Black Gibson Leather Chelsea Boots - Size US: 12.5/ UK: 12/ EU: 46
$189.00
JONES 24-7 - Men's Black Gibson Leather Chelsea Boots - Size US: 12.5/ UK: 12/ EU: 46
at: Jones Bootmaker
Tommy Hilfiger Mens Suede Chelsea Boots - Dark Coffee
$159.95
Tommy Hilfiger Mens Suede Chelsea Boots - Dark Coffee
at: Evolve Menswear
LUXURY BOOTS MADE TO HAND JAVE GREEN COLOR PREMIUM LEATHER MEN CHELSEA BOOTS
$127.39
LUXURY BOOTS MADE TO HAND JAVE GREEN COLOR PREMIUM LEATHER MEN CHELSEA BOOTS
at: Bonanza
Jones Bootmaker - Men's Dark Brown Suede Cheltenham Handmade Chelsea Boots - Size US: 11.5/ UK: 11/ EU: 45
$243.00
Jones Bootmaker - Men's Dark Brown Suede Cheltenham Handmade Chelsea Boots - Size US: 11.5/ UK: 11/ EU: 45
at: Jones Bootmaker
Leather Chelsea Boots  - BELYNR40007 / 326 191
$88.00
Leather Chelsea Boots - BELYNR40007 / 326 191
at: Pavers
Leather Chelsea Boots  - BELYNR40007 / 326 191
$88.00
Leather Chelsea Boots - BELYNR40007 / 326 191
at: Pavers
Tommy Hilfiger Mens Core Rwb Suede Chelsea Boot - Desert Sky
$159.95
Tommy Hilfiger Mens Core Rwb Suede Chelsea Boot - Desert Sky
at: Evolve Menswear
Jones Bootmaker - Men's Black Suede Cheltenham Handmade Chelsea Boots - Size US: 12.5/ UK: 12/ EU: 46
$243.00
Jones Bootmaker - Men's Black Suede Cheltenham Handmade Chelsea Boots - Size US: 12.5/ UK: 12/ EU: 46
at: Jones Bootmaker
Jones Bootmaker - Men's Black Cheltenham Handmade Chelsea Boots - Size US: 7.5/ UK: 7/ EU: 41
$243.00
Jones Bootmaker - Men's Black Cheltenham Handmade Chelsea Boots - Size US: 7.5/ UK: 7/ EU: 41
at: Jones Bootmaker
Jones Bootmaker - Women's Tan Mena Heeled Chelsea Boots - Size US: 5/ UK: 3/ EU: 36
$120.00
Jones Bootmaker - Women's Tan Mena Heeled Chelsea Boots - Size US: 5/ UK: 3/ EU: 36
at: Jones Bootmaker
Jones Bootmaker - Women's Black Patent Kefalonia Leather Chelsea Boots  - Size US: 7/ UK: 5/ EU: 38
$176.00
Jones Bootmaker - Women's Black Patent Kefalonia Leather Chelsea Boots - Size US: 7/ UK: 5/ EU: 38
at: Jones Bootmaker
Jones Bootmaker - Women's Black Kefalonia Leather Chelsea Boots  - Size US: 6/ UK: 4/ EU: 37
$176.00
Jones Bootmaker - Women's Black Kefalonia Leather Chelsea Boots - Size US: 6/ UK: 4/ EU: 37
at: Jones Bootmaker
Jones Bootmaker - Women's Black Kefalonia Leather Chelsea Boots  - Size US: 7/ UK: 5/ EU: 38
$176.00
Jones Bootmaker - Women's Black Kefalonia Leather Chelsea Boots - Size US: 7/ UK: 5/ EU: 38
at: Jones Bootmaker
Hunter Original Rubber Women's Chelsea Boots  - Colour: Purring Pink
$84.00
Hunter Original Rubber Women's Chelsea Boots - Colour: Purring Pink
at: Legend Footwear
Callum Chelsea Boot
$175.00
Callum Chelsea Boot
at: Walk London
Callum Chelsea Boot
$175.00
Callum Chelsea Boot
at: Walk London
Jones Bootmaker - Women's Sand Primrose Goodyear Welted Suede Chelsea Boots - Size US: 6/ UK: 4/ EU: 37
$182.00
Jones Bootmaker - Women's Sand Primrose Goodyear Welted Suede Chelsea Boots - Size US: 6/ UK: 4/ EU: 37
at: Jones Bootmaker
Birkenstock Highwood Slip On Mid Suede Leather Unisex Chelsea Boots  - Colour: Mocca
$205.00
Birkenstock Highwood Slip On Mid Suede Leather Unisex Chelsea Boots - Colour: Mocca
at: Legend Footwear
Birkenstock Highwood Slip On Mid Natural Leather Unisex Chelsea Boots  - Colour: Black
$194.00
Birkenstock Highwood Slip On Mid Natural Leather Unisex Chelsea Boots - Colour: Black
at: Legend Footwear
Birkenstock Highwood Slip On Mid Natural Leather Unisex Chelsea Boots  - Colour: Chocolate
$217.00
Birkenstock Highwood Slip On Mid Natural Leather Unisex Chelsea Boots - Colour: Chocolate
at: Legend Footwear
Jones Bootmaker - Women's Chocolate Carlotta Leather Chelsea Boots - Size US: 5/ UK: 3/ EU: 36
$134.00
Jones Bootmaker - Women's Chocolate Carlotta Leather Chelsea Boots - Size US: 5/ UK: 3/ EU: 36
at: Jones Bootmaker
Gabor - Women's Black Quilted Tall Chelsea Boots - Size US: 8.5/ UK: 6.5/ EU: 39.5
$162.00
Gabor - Women's Black Quilted Tall Chelsea Boots - Size US: 8.5/ UK: 6.5/ EU: 39.5
at: Jones Bootmaker
Barbour - Women's Tan Joelle Leather Chelsea Boots - Size US: 10/ UK: 8/ EU: 41
$174.00
Barbour - Women's Tan Joelle Leather Chelsea Boots - Size US: 10/ UK: 8/ EU: 41
at: Jones Bootmaker
Oscar Chelsea Boot
$165.00
Oscar Chelsea Boot
at: Walk London
Oscar Chelsea Boot
$165.00
Oscar Chelsea Boot
at: Walk London
-14%
Chelsea Boots
$992.14 $857.34
Chelsea Boots
at: Moda Di Andrea
Chelsea Boot Wellies - ITAJA36003 / 322 622
$38.00
Chelsea Boot Wellies - ITAJA36003 / 322 622
at: Pavers
-18%
Chelsea Boots Luke
$916.65 $749.49
Chelsea Boots Luke
at: Moda Di Andrea
Chelsea Boots - BELWBINS38053 / 324 184
$61.00
Chelsea Boots - BELWBINS38053 / 324 184
at: Pavers
Jones Bootmaker - Women's Black Maddalena Leather Chelsea Boots - Size US: 9/ UK: 7/ EU: 40
$134.00
Jones Bootmaker - Women's Black Maddalena Leather Chelsea Boots - Size US: 9/ UK: 7/ EU: 40
at: Jones Bootmaker
Jones Bootmaker - Women's Black Patent Croc Gessica Leather Chelsea Boots - Size US: 7/ UK: 5/ EU: 38
$162.00
Jones Bootmaker - Women's Black Patent Croc Gessica Leather Chelsea Boots - Size US: 7/ UK: 5/ EU: 38
at: Jones Bootmaker
Jones Bootmaker - Women's Dark Olive Denno Chunky Chelsea Boots - Size US: 10/ UK: 8/ EU: 41
$176.00
Jones Bootmaker - Women's Dark Olive Denno Chunky Chelsea Boots - Size US: 10/ UK: 8/ EU: 41
at: Jones Bootmaker
Jones Bootmaker - Women's Tan Forget-Me-Not Pointed Toe Chelsea Boots - Size US: 8/ UK: 6/ EU: 39
$149.00
Jones Bootmaker - Women's Tan Forget-Me-Not Pointed Toe Chelsea Boots - Size US: 8/ UK: 6/ EU: 39
at: Jones Bootmaker
Jones Bootmaker - Women's Brown Carlotta Leather Chelsea Boots - Size US: 5/ UK: 3/ EU: 36
$134.00
Jones Bootmaker - Women's Brown Carlotta Leather Chelsea Boots - Size US: 5/ UK: 3/ EU: 36
at: Jones Bootmaker