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Chelsea Boots
ShopSimon (formerly Shop Premium Outlets) Chelsea Boots
ShopSimon (formerly Shop Premium Outlets) Chelsea Boots
ShopSimon (formerly Shop Premium Outlets) Chelsea Boots
Johnston & Murphy
Mens Sutton Chelsea Boot Brown
$139.90
ShopSimon
-47%
Hereu
Alda Woven Sport In Black
$257.00
$483.00
ShopSimon
Blundstone
Chelsea-Style Ankle Boot Black
$396.00
ShopSimon
-4%
Voile Blanche
Black Leather Chelsea Boot
$317.20
$331.00
ShopSimon
-80%
Lanvin
BLACK/BLACK CHELSEA FLASH X BOLD BOOTS
$198.00
$990.00
ShopSimon
BOSS
Chelsea boots in grained leather with lug sole Black
$250.00
ShopSimon
-70%
Thomas & Vine
Hanford Plain Toe Chelsea Boot Brown
$59.99
$199.99
ShopSimon
-70%
Thomas & Vine
Ventura Tru Comfort Foam Plain Toe Chelsea Boot Brown
$59.99
$199.99
ShopSimon
-63%
Ferragamo
George 2 Chelsea Boots Purple
$461.99
$1,250.00
ShopSimon
-45%
Vance Co.
Marshall Wide Width Chelsea Boot Brown
$54.99
$99.99
ShopSimon
-57%
Ferragamo
Loreno Chelsea Boots - Wide Width Black
$558.99
$1,290.00
ShopSimon
-24%
Journee Collection
Journee Womens Violet Chelsea Boots Brown
$64.99
$85.99
ShopSimon
-64%
Rag & Bone
Eclipse Leather Chelsea Boot Brown
$206.98
$575.00
ShopSimon
-52%
Eric Michael
Womens Erika Flat Chelsea Boots In Brown
$101.00
$209.00
ShopSimon
-9%
Mia
Womens Soraya Chelsea Boots In Taupe Gray
$74.00
$81.00
ShopSimon
-45%
Vance Co.
Marshon Chelsea Boot Beige
$54.99
$99.99
ShopSimon
London Rag
bolt block heeled chelsea boots Beige
$69.99
ShopSimon
-24%
Journee Collection
Journee Womens Violet Chelsea Boots Black
$64.99
$85.99
ShopSimon
-4%
Eastland
Womens Jasmin Chelsea Heel Boot In Black
$68.00
$71.00
ShopSimon
-4%
MAYORAL
Kids Leather Chelsea Biker Boot Mid In Black
$71.00
$74.00
ShopSimon
-60%
Bogs
Mens Freedom Chelsea Boots In Cinnamon Brown
$121.00
$299.00
ShopSimon
-26%
Dockers
Mens Brookside Dress Slip-on Chelsea Boot Brown
$69.99
$95.00
ShopSimon
-23%
TruClothing
Chelsea Slip On Ankle Boots Black
$74.99
$97.49
ShopSimon
-23%
TruClothing
Slip On Suede Leather Lined Chelsea Ankle Shoes Brown
$75.00
$97.50
ShopSimon
-31%
Andrea
Chelsea Boots With Zipper Brown
$65.95
$95.00
ShopSimon
-56%
Infinity Leather
Mens Bown Suede Chelsea Boots Real Leather Lined Slip-On Brown
$87.99
$200.00
ShopSimon
-56%
Infinity Leather
Mens Brown Chelsea Slip-On Office Ankle Boots Black
$87.99
$200.00
ShopSimon
-56%
Infinity Leather
Mens Brown Chelsea Slip-On Office Ankle Boots
$87.99
$200.00
ShopSimon
-18%
Vance Co.
Vance Mens Josiah Medium and Wide Width Chelsea Boot Black
$89.99
$109.99
ShopSimon
-24%
Hunter
Original Gloss WFS2078RGL Chelsea Boots Womens 6 Black Waterproof ZPO2619
$71.98
$95.00
ShopSimon
-23%
TruClothing
Slip On Suede Leather Lined Chelsea Ankle Shoes Brown
$75.00
$97.50
ShopSimon
-23%
TruClothing
Chelsea Slip On Ankle Boots Brown
$74.99
$97.49
ShopSimon
-27%
Vance Co.
Vance Mens Salter Medium and Wide Width Plain Toe Casual Chelsea Boot Black
$79.99
$109.99
ShopSimon
-50%
Vance Co.
Garrett Wide Width Cap Toe Chelsea Boot Brown
$49.99
$99.99
ShopSimon
-19%
Chinese Laundry
Womens Chelsea Boot In Black
$84.00
$104.00
ShopSimon
-55%
Vance Co.
Thorpe Wingtip Chelsea Boot Brown
$49.99
$109.99
ShopSimon
-65%
Thomas & Vine
Jaylon Cap Toe Chelsea Boot Brown
$59.99
$169.99
ShopSimon
-15%
Vance Co.
Vance Mens Landon Chelsea Dress Boot Brown
$54.99
$64.99
ShopSimon
-29%
London Rag
frosty high platform block heel chelsea boot Black
$69.99
$99.00
ShopSimon
Blowfish
Vedder Boots Womens Black Round Toe Ankle Chelsea JOBB282
$59.99
ShopSimon
-26%
Dockers
Mens Camden Rugged Chelsea Boot Brown
$69.99
$95.00
ShopSimon
-27%
Floafers
Londoner Chelsea Boots Mens US 12 Java Black Round Toe Ankle ZPO3646 Brown
$79.99
$110.00
ShopSimon
-52%
Eric Michael
Womens Erika Flat Chelsea Boots In Black
$101.00
$209.00
ShopSimon
-41%
Dockers
Mens Tureen Dress Casual Slip On Chelsea Boot Brown
$49.98
$85.00
ShopSimon
-50%
Vance Co.
Garrett Cap Toe Chelsea Boot Brown
$49.99
$99.99
ShopSimon
-26%
Dockers
Mens Dylan Rugged Casual Chelsea Boot Black
$69.99
$95.00
ShopSimon
-25%
Rockport
Caspe Boots Mens US 8.5 Dark Natural Leather Round Toe Ankle KHD1398 Brown
$120.00
$160.00
ShopSimon
-24%
Ariat
Ariat Wexford 10061290 Boots Mens Caramel Suede Round Toe Chelsea ZOGG1365 Beige
$174.25
$230.00
ShopSimon
-26%
Dockers
Mens Dylan Rugged Casual Chelsea Boot Brown
$69.99
$95.00
ShopSimon
-29%
Rieker
Womens Chelsea Boots In Blue
$106.00
$150.00
ShopSimon
-40%
Rag & Bone
Rag & Bone Womens Sloane Suede & Leather Chelsea Boots Beige Paloma Wedge
$357.00
$595.00
ShopSimon
-24%
Rag & Bone
Womens Paloma Wedge Sloane Suede & Leather Chelsea Boots In Beige
$343.00
$450.00
ShopSimon
-49%
Proenza Schouler
Chelsea Ankle Boots in Beige Leather
$389.00
$763.00
ShopSimon
-81%
Lanvin
BLACK CHELSEA FLASH-X BOLD ANKLE BOOTS
$186.00
$990.00
ShopSimon
-29%
Eileen Fisher
Chelsea Suede Wedge Boots In Black
$168.00
$235.00
ShopSimon
-29%
Ariat
Mens Wexford Waterproof Chelsea Boot In Dark Brown
$197.00
$276.00
ShopSimon
-25%
Journee Collection
Journee Womens Junnah Medium and Wide Width Pull-on Chelsea Boots
$74.99
$99.99
ShopSimon
-30%
Cole Haan
Mens Berkshire Suede Chelsea Boot In Lava Wash Brown
$176.00
$250.00
ShopSimon
-61%
Reiss
Mina Leather Chelsea Boot Black
$149.98
$385.00
ShopSimon
-1%
Kork-ease
Womens Arline Chelsea Boot In Black
$200.00
$203.00
ShopSimon
Windsor Smith
Black Leather Chelsea Ankle Boots - Sergio
$154.99
ShopSimon
-24%
Ariat
Ariat Wexford Lug 10047056-001 Boots Womens US 8 Black Leather Chelsea KHD1397
$152.00
$200.00
ShopSimon
-24%
Marc Fisher
LTD Vanlisa Boot Womens US 10 Brown Ankle Pull-On Chelsea KHD504
$183.20
$240.00
ShopSimon
-31%
Martin Dingman
Mens Windsor Chelsea Boot In Vintage Cedar Brown
$191.00
$275.00
ShopSimon
-23%
Dr. Martens
Audrick 27148001 Black Leather Platform Chelsea Boot ZOGG258
$200.53
$260.00
ShopSimon
-26%
Carlos By Carlos Santana
Mantra Boots Mens Brown Leather Chelsea JOBB1015
$148.99
$200.00
ShopSimon
-23%
Windsor Smith
Sergio - Mens Black Slip On Leather Chelsea Boots
$162.00
$210.60
ShopSimon
-24%
FLY London
Fly London Womens Camel Brown RAWI131 Chelsea Leather Ankle Pull-On Classic Comfort Boots
$181.99
$240.00
ShopSimon
-19%
ASTORFLEX
Mens Greenflex Chelsea Boots In Dark Wine Brown
$183.00
$225.00
ShopSimon
-27%
Dr. Martens
Audrick 27148001 Boots Womens Black Leather Chelsea JOBB1660
$200.53
$275.00
ShopSimon
-30%
Ariat
Mens Comp-Toe Big Rig Chelsea Work Shoe In Dark Brown
$180.00
$258.00
ShopSimon
-61%
Reiss
Mina Leather Chelsea Boot Red
$149.98
$385.00
ShopSimon
-22%
Diba
Mens Lock Hart Chelsea Boots In Cognac Suede Tan
$108.00
$139.00
ShopSimon
-56%
Infinity Leather
Mens Brown Chelsea Slip-On Office Ankle Boots
$87.99
$200.00
ShopSimon
-33%
Doucal's
Brown Suede Chelsea Boot With Elasticated Sides
$309.00
$460.20
ShopSimon
-23%
London Brogues
Camel Suede Leather Slip On Chelsea Ankle Boots Brown
$142.50
$185.25
ShopSimon
-19%
Panama Jack
Panama Jack Womens Francesca B13 Brown Leather Chelsea Boots
$250.00
$307.99
ShopSimon
-2%
Dr. Martens
Flora Smooth Polished Chelsea Boots Black
$278.20
$283.00
ShopSimon
-8%
Panama Jack
Panama Jack Mens Beny Igloo C2 Chestnut Waterproof Leather Chelsea Boots Brown
$250.00
$272.99
ShopSimon
-17%
Voile Blanche
Burgundy Suede Chelsea Boots Black
$324.00
$392.00
ShopSimon
Timberland
Mens Redwood Falls Chelsea Boot Brown
$130.00
ShopSimon
Blundstone
Chelsea-Style Ankle Boot Black
$394.00
ShopSimon
-23%
London Brogues
Suede Leather Slip On Chelsea Ankle Boots Brown
$142.50
$185.25
ShopSimon
-12%
Dr. Martens
2976 Quad Boots Black
$298.00
$339.00
ShopSimon
Dr. Martens
Leonore Ii Chelsea Boots Black
$374.00
ShopSimon
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This season’s trends
- Dolce & Gabbana sandals
- Ecco sandals
- Gray Nike shorts
- Straw hats for men
- Prada sandals for women
- Swim trunks for women
- Moschino sandals
- Gucci shorts for men
- Gucci sandals
- Linen shirts for men
- Dr. Martens sandals
- Nike summer shoes for women
- Skechers summer shoes for women
- Clarks summer shoes for women
- HUGO BOSS sandals
- Cargo shorts for women
- Nike summer shoes for men
- Off-white sandals
- Skechers sandals
- Skechers sandals for women
- Lee shorts for women
- Amiri shorts
- Clarks sandals for women
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