- 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
BOSS
Chelsea boots in grained leather with lug sole Black
$250.00
ShopSimon
-32%
4CCCCees
Womens Plita Cella Boot In Black
$253.00
$370.00
ShopSimon
Timberland
Mens Redwood Falls Chelsea Boot
$130.00
ShopSimon
-30%
Ecco
Mens Helsinki 2 Chelsea Boot In Potting Soil Brown
$149.00
$213.00
ShopSimon
-1%
Blundstone
Black Leather Boot With Elastic Side Panels
$285.00
$289.14
ShopSimon
Blundstone
Chelsea-Style Ankle Boot Black
$396.00
ShopSimon
-25%
Rockport
Caspe Boots Mens US 8.5 Dark Natural Leather Round Toe Ankle KHD1398 Brown
$120.00
$160.00
ShopSimon
Johnston & Murphy
Mens Sutton Chelsea Boot Brown
$139.90
ShopSimon
-66%
Ferragamo
George 2 Chelsea Boots Black
$428.99
$1,250.00
ShopSimon
-55%
Vance Co.
Thorpe Wingtip Chelsea Boot Brown
$49.99
$109.99
ShopSimon
BOSS
Suede Chelsea boots with signature stripe Black
$230.00
ShopSimon
-26%
Dockers
Mens Dylan Rugged Casual Chelsea Boot Black
$69.99
$95.00
ShopSimon
-4%
Voile Blanche
Black Leather Chelsea Boot
$317.20
$331.00
ShopSimon
BOSS
Beckham x Leather Chelsea boots with elasticated panels Black
$499.00
ShopSimon
BOSS
Suede Chelsea boots with signature stripe Brown
$230.00
ShopSimon
-46%
Gianvito Rossi
Chester Chelsea Boots in Black Leather
$691.00
$1,286.00
ShopSimon
-45%
Bally
Scavone 6237884 Mens Agata Calf Leather Chelsea Boots Black
$742.50
$1,350.00
ShopSimon
BOSS
Suede Chelsea boots with elasticated panels Black
$199.00
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
-8%
Santoni
Ultra-Lightweight Black Leather Chelsea Boot
$873.00
$947.00
ShopSimon
-27%
Floafers
Londoner Chelsea Boots Mens US 12 Java Black Round Toe Ankle ZPO3646 Brown
$79.99
$110.00
ShopSimon
-45%
Vance Co.
Marshall Wide Width Chelsea Boot Gray
$54.99
$99.99
ShopSimon
-23%
TruClothing
Chelsea Slip On Ankle Boots Black
$74.99
$97.49
ShopSimon
-4%
MAYORAL
Kids Leather Chelsea Biker Boot Mid In Black
$71.00
$74.00
ShopSimon
-4%
Eastland
Womens Jasmin Chelsea Heel Boot In Black
$68.00
$71.00
ShopSimon
-57%
Eric Michael
Women Charlie Boot In Grey Gray
$88.00
$205.00
ShopSimon
-19%
Chinese Laundry
Womens Chelsea Boot In Black
$84.00
$104.00
ShopSimon
-35%
Vance Co.
Vance Mens Landon Chelsea Dress Boot Gray
$54.99
$84.99
ShopSimon
-18%
Vance Co.
Vance Mens Josiah Medium and Wide Width Chelsea Boot Black
$89.99
$109.99
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 Brown Chelsea Slip-On Office Ankle Boots Black
$87.99
$200.00
ShopSimon
-27%
Vance Co.
Vance Mens Salter Medium and Wide Width Plain Toe Casual Chelsea Boot Black
$79.99
$109.99
ShopSimon
Blowfish
Vedder Boots Womens Black Round Toe Ankle Chelsea JOBB282
$59.99
ShopSimon
-29%
London Rag
frosty high platform block heel chelsea boot Black
$69.99
$99.00
ShopSimon
-24%
Journee Collection
Journee Womens Violet Chelsea Boots Black
$64.99
$85.99
ShopSimon
-52%
Eric Michael
Womens Erika Flat Chelsea Boots In Brown
$101.00
$209.00
ShopSimon
-23%
TruClothing
Chelsea Slip On Ankle Boots Brown
$74.99
$97.49
ShopSimon
-52%
Eric Michael
Womens Erika Flat Chelsea Boots In Black
$101.00
$209.00
ShopSimon
-56%
Infinity Leather
Mens Bown Suede Chelsea Boots Real Leather Lined Slip-On Brown
$87.99
$200.00
ShopSimon
-15%
Vance Co.
Vance Mens Landon Chelsea Dress Boot Brown
$54.99
$64.99
ShopSimon
-27%
Vance Co.
Vance Mens Salter Medium and Wide Width Plain Toe Casual Chelsea Boot Brown
$79.99
$109.99
ShopSimon
-65%
Thomas & Vine
Jaylon Cap Toe Chelsea Boot Brown
$59.99
$169.99
ShopSimon
-56%
Infinity Leather
Mens Brown Chelsea Slip-On Office Ankle Boots
$87.99
$200.00
ShopSimon
-31%
Andrea
Chelsea Boots With Zipper Brown
$65.95
$95.00
ShopSimon
-50%
Vance Co.
Garrett Wide Width Cap Toe Chelsea Boot Brown
$49.99
$99.99
ShopSimon
-41%
Dockers
Mens Tureen Dress Casual Slip On Chelsea Boot Brown
$49.98
$85.00
ShopSimon
-35%
Vance Co.
Vance Mens Landon Wide Width Chelsea Dress Boot Brown
$54.99
$84.99
ShopSimon
-45%
Vance Co.
Marshall Wide Width Chelsea Boot Brown
$54.99
$99.99
ShopSimon
-26%
Dockers
Mens Brookside Dress Slip-on Chelsea Boot Brown
$69.99
$95.00
ShopSimon
-19%
Hunter
Womens Original Refined Chelsea Gloss Boot In Stratus Gray
$117.00
$145.00
ShopSimon
-26%
Dockers
Mens Camden Rugged Chelsea Boot Brown
$69.99
$95.00
ShopSimon
-25%
Journee Collection
Journee Womens Junnah Medium and Wide Width Pull-on Chelsea Boots
$74.99
$99.99
ShopSimon
-24%
Hunter
Original Gloss WFS2078RGL Chelsea Boots Womens 6 Black Waterproof ZPO2619
$71.98
$95.00
ShopSimon
Dr. Martens
Leather Chelsea Boots Brown
$302.00
ShopSimon
-26%
Dockers
Mens Dylan Rugged Casual Chelsea Boot Brown
$69.99
$95.00
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
Blundstone
Chelsea-Style Ankle Boot Black
$394.00
ShopSimon
-10%
Blundstone
Black Leather Boot With Fuchsia Elastic Panels
$311.00
$347.10
ShopSimon
-73%
Magda Butrym
Chelsea Ankle Boots in Black Leather
$358.00
$1,326.00
ShopSimon
-24%
Journee Collection
Journee Womens Violet Chelsea Boots Brown
$64.99
$85.99
ShopSimon
-68%
Jil Sander
Ribbed Sock Chelsea Ankle Boots in Black Leather
$442.00
$1,390.00
ShopSimon
-33%
Doucal's
Brown Suede Chelsea Boot With Elasticated Sides
$309.00
$460.20
ShopSimon
-17%
Voile Blanche
Burgundy Suede Chelsea Boots Black
$324.00
$392.00
ShopSimon
-9%
Mia
Womens Soraya Chelsea Boots In Taupe Gray
$74.00
$81.00
ShopSimon
-10%
Blundstone
Washed Brown Lug Boot With Elastic Side Inserts
$339.00
$377.00
ShopSimon
-8%
Panama Jack
Panama Jack Mens Beny Igloo C1 Black Waterproof Leather Chelsea Boots
$250.00
$272.99
ShopSimon
-8%
Panama Jack
Panama Jack Mens Beny Igloo C2 Chestnut Waterproof Leather Chelsea Boots Brown
$250.00
$272.99
ShopSimon
-2%
Dr. Martens
Flora Smooth Polished Chelsea Boots Black
$278.20
$283.00
ShopSimon
-46%
Ferragamo
Chelsea Suede Boots Blue
$300.08
$560.00
ShopSimon
-19%
Panama Jack
Panama Jack Womens Francesca B13 Brown Leather Chelsea Boots
$250.00
$307.99
ShopSimon
-12%
Dr. Martens
2976 Quad Boots Black
$298.00
$339.00
ShopSimon
Dr. Martens
Graeme Chelsea Boots Black
$355.00
ShopSimon
-7%
Dr. Martens
Chelsea Boot 2976 Dark Brown
$272.00
$293.00
ShopSimon
-29%
London Rag
frosty high platform block heel chelsea boot White
$69.99
$99.00
ShopSimon
Dr. Martens
Chelsea Boots Black
$374.00
ShopSimon
Dr. Martens
Leonore Ii Chelsea Boots Black
$374.00
ShopSimon
-46%
Stuart Weitzman
Sondra Sleek Chelsea Boot Black
$324.26
$595.00
ShopSimon
-1%
Blundstone
1910 Suede Leather Ankle Boot Black
$285.00
$287.92
ShopSimon
-44%
Proenza Schouler
Leather Chelsea Boot Black
$499.98
$900.00
ShopSimon
-80%
Lanvin
BLACK/BLACK CHELSEA FLASH X BOLD BOOTS
$198.00
$990.00
ShopSimon
-1%
Kork-ease
Womens Arline Chelsea Boot In Black
$200.00
$203.00
ShopSimon
-24%
Ariat
Ariat Wexford Lug 10047056-001 Boots Womens US 8 Black Leather Chelsea KHD1397
$152.00
$200.00
ShopSimon
- 1 of 2
- 2
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