- All Products
- Fashion
- ShopSimon
- Shoes
- Boots
-
Chelsea Boots
ShopSimon (formerly Shop Premium Outlets) Chelsea Boots
ShopSimon (formerly Shop Premium Outlets) Chelsea Boots
ShopSimon (formerly Shop Premium Outlets) Chelsea Boots
-30%
Journee Collection
Womens Violet Chelsea Boots Black
$64.99
$93.00
ShopSimon
-31%
Journee Collection
Womens Junnah Medium and Wide Width Pull-on Chelsea Boots
$74.99
$108.00
ShopSimon
-30%
Journee Collection
Womens Violet Chelsea Boots Gold
$64.99
$93.00
ShopSimon
Saint Morta
Chunky Chelsea Boot Mocha CHUNKY-MOCHA Mens Brown
$150.00
ShopSimon
-41%
Ariat
Mens Big Rig Water Proof Chelsea Work Boots In Iron Coffee
$118.00
$200.00
ShopSimon
-30%
Journee Collection
Womens Isabeau Medium and Wide Width Knit Collar Chelsea Boots
$69.99
$99.99
ShopSimon
-63%
Santoni
Mens Easy Chelsea Boot In Tan
$318.00
$850.00
ShopSimon
-19%
Merrell
Mens Moab Adventure 3 Chelsea Polar Waterproof Boots In Brown
$122.00
$150.00
ShopSimon
-15%
Blundstone
Womens Chelsea Boots In Stout Brown
$226.00
$267.00
ShopSimon
-51%
To Boot New York
Mens Erikson Calf Leather Chelsea Boot In Burnished Tan Brown
$254.00
$518.00
ShopSimon
-53%
Bally
Chelly PVC Chelsea Boots, Brand Size 36 ( US Size 5.5 ) Black
$172.57
$365.00
ShopSimon
-50%
Magnanni
Mens Marton Chelsea Boot In Torba Suede Brown
$263.00
$525.00
ShopSimon
-44%
Ecco
Womens Sartorelle 25 Chelsea Boots In Cognac Brown
$142.00
$253.00
ShopSimon
-35%
Lems Shoes
Mens Waterproof Chelsea Barefoot Boot In Espresso Brown
$124.00
$190.00
ShopSimon
-60%
Santoni
Mens Easy Chelsea Boots In Dark Brown
$337.00
$850.00
ShopSimon
-72%
Ferragamo
Ferragamo Toren Vara Chain Ankle Boots, Size 7 C Black
$347.47
$1,250.00
ShopSimon
-16%
UGG
Mens Neumel Chelsea Boot In Chestnut Pink
$169.00
$200.00
ShopSimon
-17%
Olukai
Womens Pehuea Mid Chelsea Boots In Dark Java/dark Java Gray
$116.00
$140.00
ShopSimon
-20%
Blundstone
Mens Classics 585 Chelsea Boots In Brown
$184.00
$229.00
ShopSimon
-59%
Ann Mashburn
Womens Tall Lug Sole Chelsea Boot In Black Leather
$174.00
$425.00
ShopSimon
-80%
Thomas & Vine
Hanford Plain Toe Chelsea Boot Black
$40.00
$199.99
ShopSimon
-37%
Dockers
Mens Camden Rugged Chelsea Boot
$59.99
$95.00
ShopSimon
-37%
Dockers
Mens Camden Rugged Chelsea Boot
$59.99
$95.00
ShopSimon
-37%
Dockers
Mens Camden Rugged Chelsea Boot
$59.99
$95.00
ShopSimon
-56%
Bally
Ginny Chunky Chelsea Boots White
$459.92
$1,050.00
ShopSimon
-43%
Ferragamo
Flash Chelsea Boots Black
$657.99
$1,150.00
ShopSimon
-43%
Ferragamo
Doran Chelsea Boots Black
$680.99
$1,190.00
ShopSimon
-43%
Ferragamo
Doran Suede Chelsea Boots Brown
$680.99
$1,190.00
ShopSimon
-39%
Versace
Mid-Calf Leather Chunky Chelsea Boots in Black Leather
$749.00
$1,231.00
ShopSimon
-29%
Ferragamo
Mens Isidoro Chelsea Boots In Brown
$1,024.00
$1,450.00
ShopSimon
-13%
Santoni
Black Leather Chelsea Ankle Boots
$1,136.61
$1,308.38
ShopSimon
Santoni
Handcrafted Suede Non-Slip Boots Black
$1,161.66
ShopSimon
-13%
Santoni
Justin Suede Beatles Ankle Boots Brown
$1,485.55
$1,707.55
ShopSimon
-11%
Churchs
Vintage Suede Elastic Side Boots Brown
$1,226.23
$1,372.14
ShopSimon
-9%
Vance Co.
Garrett Cap Toe Chelsea Boot Brown
$99.99
$109.99
ShopSimon
-9%
Vance Co.
Garrett Wide Width Cap Toe Chelsea Boot Brown
$99.99
$109.99
ShopSimon
-9%
Vance Co.
Garrett Wide Width Cap Toe Chelsea Boot Brown
$99.99
$109.99
ShopSimon
-24%
Journee Collection
Journee Womens Violet Chelsea Boots Brown
$64.99
$85.99
ShopSimon
-25%
Journee Collection
Journee Womens Junnah Medium and Wide Width Pull-on Chelsea Boots
$74.99
$99.99
ShopSimon
-25%
Saint Morta
Chunky Chelsea Boot Mocha CHUNKY-MOCHA Mens Brown
$112.00
$150.00
ShopSimon
-24%
Journee Collection
Journee Womens Violet Chelsea Boots Black
$64.99
$85.99
ShopSimon
-43%
Ecco
Mens Grainer Chelsea Slip-On Boot In Black
$124.00
$219.00
ShopSimon
-30%
Kork-ease
Womens Arline Chelsea Boot In Black
$141.00
$200.00
ShopSimon
-69%
Proenza Schouler
Leather Chelsea Boot Black
$279.98
$900.00
ShopSimon
-61%
Proenza Schouler
Leather Chelsea Boot Black
$350.98
$900.00
ShopSimon
Vance Co.
Thorpe Wingtip Chelsea Boot Brown
$109.99
ShopSimon
-37%
Dockers
Mens Brookside Polished Dress Chelsea Boot Green
$59.99
$95.00
ShopSimon
-55%
Rieker
Womens Chelsea Boots In Blue
$68.00
$150.00
ShopSimon
-26%
Dockers
Mens Dylan Rugged Casual Chelsea Boot Green
$69.99
$95.00
ShopSimon
-26%
Dockers
Mens Dylan Rugged Casual Chelsea Boot Green
$69.99
$95.00
ShopSimon
-26%
Dockers
Mens Dylan Rugged Casual Chelsea Boot Green
$69.99
$95.00
ShopSimon
-26%
Dockers
Mens Dylan Rugged Casual Chelsea Boot Green
$69.99
$95.00
ShopSimon
-26%
Dockers
Mens Dylan Rugged Casual Chelsea Boot Green
$69.99
$95.00
ShopSimon
-26%
Dockers
Mens Dylan Rugged Casual Chelsea Boot Green
$69.99
$95.00
ShopSimon
-26%
Dockers
Mens Dylan Rugged Casual Chelsea Boot Green
$69.99
$95.00
ShopSimon
-26%
Dockers
Mens Dylan Rugged Casual Chelsea Boot Green
$69.99
$95.00
ShopSimon
-26%
Dockers
Mens Dylan Rugged Casual Chelsea Boot Green
$69.99
$95.00
ShopSimon
-26%
Dockers
Mens Dylan Rugged Casual Chelsea Boot Green
$69.99
$95.00
ShopSimon
-26%
Dockers
Mens Dylan Rugged Casual Chelsea Boot Green
$69.99
$95.00
ShopSimon
-26%
Dockers
Mens Dylan Rugged Casual Chelsea Boot Green
$69.99
$95.00
ShopSimon
-80%
Rag & Bone
Eclipse Leather Chelsea Boot Brown
$116.99
$575.00
ShopSimon
Vance Co.
Marshon Chelsea Boot Beige
$99.99
ShopSimon
-24%
Kenneth Cole
Radell Boots Womens Mauve Brown Suede Pull On Chelsea LION306
$106.50
$140.00
ShopSimon
-23%
Steve Madden
Leopold Boots Women Brown Suede Round Toe Ankle Chelsea LION261
$84.15
$110.00
ShopSimon
-23%
Steve Madden
Leopold Boots Womens Brown Suede Round Toe Ankle Chelsea LION186
$84.15
$110.00
ShopSimon
Vance Co.
Marshall Wide Width Chelsea Boot Brown
$99.99
ShopSimon
-4%
Andrea
Chelsea Boots With Zipper Brown
$90.95
$95.00
ShopSimon
-15%
Vance Co.
Vance Mens Landon Wide Width Chelsea Dress Boot Brown
$84.99
$99.99
ShopSimon
-36%
Andrea
Womens Animal Print Chelsea Boots In Leopard Brown
$51.00
$80.00
ShopSimon
-50%
Vance Co.
Vance Mens Salter Medium and Wide Width Plain Toe Casual Chelsea Boot Brown
$55.00
$109.99
ShopSimon
-23%
TruClothing
Chelsea Slip On Ankle Boots Brown
$74.99
$97.49
ShopSimon
-56%
Infinity Leather
Mens Brown Chelsea Slip-On Office Ankle Boots
$87.99
$200.00
ShopSimon
-23%
TruClothing
Slip On Suede Leather Lined Chelsea Ankle Shoes Brown
$75.00
$97.50
ShopSimon
-23%
TruClothing
Slip On Suede Leather Lined Chelsea Ankle Shoes Brown
$75.00
$97.50
ShopSimon
-56%
Infinity Leather
Mens Bown Suede Chelsea Boots Real Leather Lined Slip-On Brown
$87.99
$200.00
ShopSimon
-65%
Thomas & Vine
Jaylon Cap Toe Chelsea Boot Brown
$59.99
$169.99
ShopSimon
-70%
Thomas & Vine
Ventura Tru Comfort Foam Plain Toe Chelsea Boot Brown
$59.99
$199.99
ShopSimon
-9%
Vance Co.
Garrett Cap Toe Chelsea Boot Brown
$99.99
$109.99
ShopSimon
-76%
Reiss
Mina Leather Chelsea Boot Red
$93.99
$385.00
ShopSimon
-35%
Steve Madden
Clarisa Chelsea Boots Sand Leather Platform JZZ1114 Beige
$129.95
$200.00
ShopSimon
-22%
Franco Sarto
Linc Boots Women Brown Leather Side Zipper Chelsea Bootie LION603
$136.00
$175.00
ShopSimon
-14%
Steve Madden
Zoltin Boots Womens Mushroom Suede Block Heel Chelsea HTAT873 Brown
$119.99
$140.00
ShopSimon
-26%
Naturalizer
Womens Soul Naturalizer Jayda Boots Brown Platform Ankle Chelsea RHS6248
$139.99
$190.00
ShopSimon
-35%
Sorel
Emelie II 2004921-242 Boots B Dark Amber Leather Chelsea HTAT716 Brown
$149.95
$230.00
ShopSimon
-74%
Proenza Schouler
Chelsea Ankle Boots in Beige Leather
$199.00
$763.00
ShopSimon
-25%
Madewell
Paulette Short Chelsea Earthen Sand NH947-953 Womens Brown
$148.00
$198.00
ShopSimon
-17%
Alegria
Meadow Boots Chocolate Leather Elastic Gore Chelsea HAWK213 Brown
$150.00
$180.00
ShopSimon
-24%
Marc Fisher
Womens Marc Fisher LTD Vanlisa Boot US 10 Brown Ankle Pull-On Chelsea KHD504
$183.20
$240.00
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
about products and deals