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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
-17%
Windsor Smith
Brown Leather Chelsea Ankle Boots - Sergio
$127.99
$154.99
ShopSimon
-35%
Bogs
Mens Casual Chelsea Boots In Brown
$85.00
$130.00
ShopSimon
-14%
Madewell
Womens Madewell The Wyckoff NN020 Boots Raisin Leather Chelsea HTAT511 Brown
$198.00
$230.00
ShopSimon
Johnston & Murphy
Mens Sutton Chelsea Boot Brown
$139.90
ShopSimon
-29%
Rocky
Mens Legacy 33 Waterproof Chelsea Work Boot In Brown
$114.00
$160.00
ShopSimon
-29%
TERRITORY
Yellowstone Water Resistant Chelsea Boot Brown
$119.99
$169.99
ShopSimon
-23%
London Brogues
Suede Leather Slip On Chelsea Ankle Boots Brown
$142.50
$185.25
ShopSimon
-24%
FLY London
Fly London Womens Camel Brown RAWI131 Chelsea Leather Ankle Pull-On Classic Comfort Boots
$181.99
$240.00
ShopSimon
-37%
Blundstone
1306 Bootss Rustic Brown Leather Round Toe Chelsea HTAT708
$209.34
$330.00
ShopSimon
-36%
Mustang
Mens Mokka Brown Water-Resistant Chelsea Ankle Boots
$127.99
$200.00
ShopSimon
Vance Co.
Thorpe Wingtip Chelsea Boot Brown
$109.99
ShopSimon
-65%
Blondo
Womens Raquel Chelsea Boot In Light Grey Cow Suede/textile
$56.00
$159.00
ShopSimon
-58%
Sorel
Womens Caribou Chelsea Boot In Jet/pixel Black
$79.00
$190.00
ShopSimon
-56%
Infinity Leather
Mens Brown Chelsea Slip-On Office Ankle Boots
$87.99
$200.00
ShopSimon
-43%
Ariat
Men Big Rig Chelsea Comp-Toe Work Boot - Extra Wide In Iron Coffee Brown
$126.00
$220.00
ShopSimon
-25%
Rockport
Mens Rockport Caspe Boots US 8.5 Dark Natural Leather Round Toe Ankle KHD1398 Brown
$120.00
$160.00
ShopSimon
-26%
Dockers
Mens Dylan Rugged Casual Chelsea Boot
$69.99
$95.00
ShopSimon
-26%
Dockers
Mens Dylan Rugged Casual Chelsea Boot
$69.99
$95.00
ShopSimon
-26%
Dockers
Mens Dylan Rugged Casual Chelsea Boot
$69.99
$95.00
ShopSimon
-26%
Dockers
Mens Dylan Rugged Casual Chelsea Boot
$69.99
$95.00
ShopSimon
-26%
Dockers
Mens Dylan Rugged Casual Chelsea Boot
$69.99
$95.00
ShopSimon
-26%
Dockers
Mens Dylan Rugged Casual Chelsea Boot
$69.99
$95.00
ShopSimon
-30%
Hunter
Original Chelsea Boot Red
$107.98
$155.00
ShopSimon
-72%
Chaco
Womens Fields Chelsea Waterproof Boot In Chestnut Brown
$92.00
$334.00
ShopSimon
-43%
Mustang
Womens Burgundy Chelsea Ankle Boots Gold
$114.99
$200.00
ShopSimon
-43%
Dockers
Mens Ander Leather Chelsea Boot Yellow
$59.99
$105.00
ShopSimon
-25%
Nisolo
Womens Nisolo Carmen Boots Beige Suede Round Toe Ankle Chelsea RHS6298
$239.99
$320.00
ShopSimon
-63%
Proenza Schouler
Leather Chelsea Boot Brown
$332.99
$900.00
ShopSimon
-37%
Andrea
Womens Leather Chelsea Boots In Black
$56.00
$89.00
ShopSimon
-18%
Vance Co.
Vance Mens Josiah Medium and Wide Width Chelsea Boot Black
$89.99
$109.99
ShopSimon
-26%
Steve Madden
Womens Steve Madden Hawke HAWK03M1 Boots Black Leather Chelsea Boots JOBB1727
$103.95
$140.00
ShopSimon
-23%
TruClothing
Chelsea Slip On Ankle Boots Black
$74.99
$97.49
ShopSimon
-50%
Vance Co.
Vance Mens Salter Medium and Wide Width Plain Toe Casual Chelsea Boot Black
$55.00
$109.99
ShopSimon
-56%
Infinity Leather
Mens Brown Chelsea Slip-On Office Ankle Boots Black
$87.99
$200.00
ShopSimon
-35%
Eastland
Womens Jasmin Chelsea Heel Boot In Black
$46.00
$71.00
ShopSimon
-42%
Born
Womens Skyway Chelsea Boots In Brown
$160.00
$276.00
ShopSimon
-45%
Blundstone
Mens Classics 585 Boots In Rustic Brown
$216.00
$391.00
ShopSimon
-35%
Blundstone
1351 Boots Rustic Brown Leather Elastic Gore Chelsea HTAT710
$247.80
$380.00
ShopSimon
-44%
Rag & Bone
Womens Paloma Wedge Sloane Suede & Leather Chelsea Boots In Beige
$254.00
$450.00
ShopSimon
-42%
Birkenstock
Mens Highwood Slip On Chelsea Boot In Mocha Brown
$210.00
$363.00
ShopSimon
-36%
Madden Girl
Tippah Boots White Faux Leather Platform Chelsea JZZ1118
$89.00
$140.00
ShopSimon
-11%
Panama Jack
Panama Jack Womens Francesca B13 Brown Leather Chelsea Boots
$250.00
$279.99
ShopSimon
-7%
Panama Jack
Panama Jack Mens Beny Igloo C2 Chestnut Waterproof Leather Chelsea Boots Brown
$250.00
$269.99
ShopSimon
-13%
Abercrombie & Fitch
Lorice Ankle Boots Womens Oatmeal Chelsea HTAT1163 White
$65.00
$75.00
ShopSimon
-85%
Magda Butrym
Chelsea Ankle Boots in Black Leather
$202.00
$1,326.00
ShopSimon
-23%
Windsor Smith
Sergio - Mens Black Slip On Leather Chelsea Boots
$162.00
$210.60
ShopSimon
-17%
Windsor Smith
Black Leather Chelsea Ankle Boots - Sergio
$127.99
$154.99
ShopSimon
-72%
Reiss
Mina Leather Chelsea Boot Black
$108.98
$385.00
ShopSimon
-20%
Dr. Martens
Womens Dr. Martens 2976 Boots Black Leather Round Toe Chelsea VER999
$152.00
$190.00
ShopSimon
-35%
Birkenstock
Stalon Ii 1017318 Boots 5-Black Leather Chelsea JZZ1117
$169.98
$260.00
ShopSimon
-25%
Thomas & Vine
Nash Wingtip Chelsea Boot Black
$119.99
$159.99
ShopSimon
-25%
Saint Morta
Chunky Chelsea Boot Black / Gum SMCHUNKCHBT-BLK Mens
$96.00
$128.00
ShopSimon
-24%
United Nude
Jimmy Chelsea Mens Black
$345.00
$455.00
ShopSimon
-35%
United Nude
Jimmy Chelsea Mens
$345.00
$534.75
ShopSimon
-35%
United Nude
Bull Chelsea
$295.00
$454.25
ShopSimon
-35%
United Nude
Jimmy Chelsea Mens
$345.00
$534.75
ShopSimon
-45%
Stacy Adams
Mens Perrin Chelsea Mid Boots In Congnac
$184.00
$334.00
ShopSimon
-31%
United Nude
Grip Chelsea Lo Iv
$315.00
$454.25
ShopSimon
-43%
Mustang
Womens Burgundy Chelsea Ankle Boots White
$114.99
$200.00
ShopSimon
-15%
Mia
Fala MH240801 Boots Womens Sand Leather Block Heel Chelsea HTAT1072 White
$110.00
$130.00
ShopSimon
-35%
United Nude
Bull Chelsea Silver
$295.00
$454.25
ShopSimon
-24%
United Nude
Jimmy Chelsea Mens Silver
$345.00
$455.00
ShopSimon
United Nude
Grip-chelsea-mid-iii
$477.25
ShopSimon
-36%
Andrea
Womens Leather Chelsea Boots In Burgundy White
$54.00
$85.00
ShopSimon
-51%
Mezlan
Mens Cervantes Chelsea Boot In Black
$227.00
$460.00
ShopSimon
-83%
Stuart Weitzman
Black Leather Bedford Bootie
$196.58
$1,150.00
ShopSimon
-60%
Soludos
Womens Greenpoint Chelsea Boot In Black Leather
$160.00
$403.00
ShopSimon
-59%
Stuart Weitzman
Sondra Sleek Chelsea Boot Black
$244.92
$595.00
ShopSimon
-15%
Blundstone
1630 Boots Black Leather Elastic Side Ankle Chelsea ZAP901
$245.36
$290.00
ShopSimon
-45%
Frye
Womens Sabrina Chelsea Boots In Black
$274.00
$497.00
ShopSimon
-67%
Proenza Schouler
Leather Chelsea Boot Black
$299.98
$900.00
ShopSimon
-55%
Hereu
Alda Woven Sport In Black
$219.00
$483.00
ShopSimon
-7%
Panama Jack
Panama Jack Mens Beny Igloo C1 Black Waterproof Leather Chelsea Boots
$250.00
$269.99
ShopSimon
-68%
Proenza Schouler
Leather Chelsea Boot White
$284.99
$900.00
ShopSimon
-27%
Floafers
Mens Floafers Londoner Chelsea Boots US 12 Java Black Round Toe Ankle ZPO3646 Brown
$79.99
$110.00
ShopSimon
Vance Co.
Marshall Wide Width Chelsea Boot Gray
$99.99
ShopSimon
-17%
Dr. Scholls
Northbound Boots Womens Charcoal Round Toe Chelsea HTAT1111 Gray
$100.00
$120.00
ShopSimon
-65%
Thomas & Vine
Jaylon Cap Toe Chelsea Boot Gray
$59.99
$169.99
ShopSimon
-16%
Steve Madden
Womens Steve Madden Dorothea DOTH01S1 Boots Mushroom Suede Chelsea HTAT400 Gray
$59.13
$70.00
ShopSimon
-40%
Mia
Womens Soraya Chelsea Boots In Taupe Gray
$49.00
$81.00
ShopSimon
-3%
Hogan
Brown Calfskin Chelsea Boots
$545.24
$561.30
ShopSimon
-52%
Ferragamo
Ferragamo Ladies Black Chelsea Ankle Boots
$473.77
$995.00
ShopSimon
-9%
Hogan
Chelsea Boot Black
$523.89
$572.69
ShopSimon
-24%
Churchs
ChurchS Ketsby perforated polished chelsea boots Red
$527.00
$690.00
ShopSimon
-20%
Rag & Bone
Rag & Bone Womens Sloane Suede & Leather Chelsea Boots Beige Paloma Wedge
$596.00
$745.00
ShopSimon
-43%
Ferragamo
Rook Chelsea Boots Red
$600.99
$1,050.00
ShopSimon
-28%
La Canadienne
Womens La Canadienne Teddy Boots US Black Leather Block Heel Chelsea ZOGG1821
$575.00
$800.00
ShopSimon
-16%
Stuart Weitzman
Womens Stuart Weitzman Emerson SJ336 Boots Black Leather Chelsea ZOGG2004
$675.00
$800.00
ShopSimon
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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