Regular Chelsea Ankle
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$100 to $250
38
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$250 to $500
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Rated 5 out of 5 stars
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13
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Rated 4 out of 5 stars
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43
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15
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Rated 1 out of 5 stars
1
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Show 110 Items
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Dr. Scholl's Northbound Women's Chelsea Boots
$59.99
Sale
$100.00 Reg.
Rated 4 out of 5 stars
(78)
Sonoma Goods For Life® Ilon Boys Chelsea Boots
$20.97
Sale
$34.99 Reg.
Rated 4.8 out of 5 stars
(20)
Cliffs by White Mountain Durbon Women's Ankle Boots
$61.99
Sale
$89.00 Reg.
Rated 4.6 out of 5 stars
(61)
Territory Holloway Men's Leather Chelsea Boots
$35.99
Clearance
$159.99 Reg.
Rated 3.7 out of 5 stars
(3)
Sonoma Goods For Life® Vorsey Men's Chelsea Boots
$35.97
Sale
$59.99 Reg.
Rated 4.6 out of 5 stars
(190)
Rocket Dog Rainbow Women's Chelsea Rain Boots
$42.99 - $46.99
Sale
$54.95 - $59.95 Reg.
Rated 4.4 out of 5 stars
(211)
Rocket Dog Maylon Women's Chelsea Boots
$54.99
Sale
$69.95 Reg.
Rated 4.1 out of 5 stars
(129)
Cliffs By White Mountain Maximus Women's Chelsea Ankle Boots
$58.99
Sale
$99.00 Reg.
Rated 3.3 out of 5 stars
(3)
Eastland Tamara Women's High Heeled Chelsea Boots
$80.00
Rated 4.4 out of 5 stars
(16)
Journee Blanche Women's Pull-On Block Heel Chelsea Ankle Boots
$69.99
Sale
$99.99 Orig.
Rated 3.6 out of 5 stars
(17)
Nunn Bush® Delton Men's Chelsea Boots
$95.00
Cliffs By White Mountain Mingo Women's Chelsea Boots Slip-On Block Heel
$58.99
Sale
$99.00 Reg.
Rated 3.7 out of 5 stars
(6)
Thomas & Vine Jaylon Men's Leather Chelsea Boots
$38.24
Clearance
$169.99 Reg.
Rated 4.5 out of 5 stars
(2)
Propet Tyler Men's Waterproof Ankle Boots
$139.95
Rated 4.2 out of 5 stars
(20)
Easy Street Wyatt Women's Comfort Chelsea Boots
$74.99
Rated 3.5 out of 5 stars
(29)
Journee Ivette Women's Ankle Boots
$77.97
Sale
$129.99 Reg.
Rated 4 out of 5 stars
(68)
Aerosoles Poshan Women's Slip-On Block Heel Ankle Boots in Medium & Wide Calf
$129.00
Skechers Hands Free Slip-ins® Easy Going Casual Icon Women's Boots
$53.97
Sale
$89.99 Reg.
Rated 4.3 out of 5 stars
(27)
London Rag Prolt Women's Chelsea Boots
$66.99
Rated 3.9 out of 5 stars
(7)
Vance Salter Men's Casual Chelsea Boots
$109.99
Rated 4.8 out of 5 stars
(6)
Dr. Scholl's Time Off Up Zip Women's Boots
$64.99
Sale
$130.00 Reg.
Rated 5 out of 5 stars
(1)
Dr. Scholl's Mara Women's Chelsea Boots
$68.99
Sale
$115.00 Reg.
Rated 5 out of 5 stars
(1)
Journee Drizzle Women's Waterproof Round Toe Rain Boots
$49.99
Sale
$71.99 Orig.
Rated 2.8 out of 5 stars
(4)
Dockers® Ander Men's Leather Chelsea Boots
$100.00
Nunn Bush® Excavate Men's Moc Toe Chelsea Boots
$95.00
Rated 4.7 out of 5 stars
(19)
Nunn Bush® Karnak Men's Plain Toe Chelsea Slip-On Boots
$120.00
Rated 4.6 out of 5 stars
(13)
Men's Thomas & Vine Tru Comfort Chelsea Boots
$44.99
Clearance
$199.99 Reg.
Rated 5 out of 5 stars
(1)
Nunn Bush® Otis II Men's Leather Chelsea Boots
$120.00
Rated 3.8 out of 5 stars
(10)
Andrea Women's Leather Short Chelsea Boots 90569
$85.00
Rated 5 out of 5 stars
(1)
Gino Vitale Men's Wingtip Brogue Two-Tone Chelsea Boots
$89.99
Rated 5 out of 5 stars
(1)
New York & Company Bauer Chelsea Men's Boots
$54.00
Rated 3 out of 5 stars
(2)
Bogs Sauvie Chelsea II Men's Waterproof Boots
$110.00
Rated 4.1 out of 5 stars
(220)
Eastland Juniper Chelsea Boots
$75.00
Rated 4.2 out of 5 stars
(9)
Nunn Bush® Trekker Men's Moc Toe Chelsea Boots
$85.00
Georgia Boots AMP LT Men's Wedge Chelsea Work Boots
$170.00
Rated 4.4 out of 5 stars
(29)
VANCE Garrett Men's Chelsea Boots
$59.97 - $99.99
$99.99 Reg.
Select Styles on Sale
Rated 3.9 out of 5 stars
(14)
Dr. Scholl's Parker Women's Zip Ankle Boots
$56.99
Sale
$115.00 Reg.
Rated 2.4 out of 5 stars
(5)
Jumping Beans® Gordino Toddler Chelsea Boots
$14.97
Sale
$24.99 Reg.
Rated 5 out of 5 stars
(3)
Top Rated
Eastland Daily Double Men's Leather Chelsea Boots
$125.00
Rated 4.9 out of 5 stars
(11)
Ankle Boots Mid-height Heels Zipper Dressy Chelsea Booties for Women
$83.49
Rated 5 out of 5 stars
(1)
Bogs Amanda II Women's Waterproof Chelsea Rain Boots
$110.00
Rated 4.1 out of 5 stars
(131)
Refresh Women's Casual Chelsea Booties 173084
$70.80
$82.60
Georgia Boots Wedge Men's Waterproof Chelsea Work Boots
$175.00
Rated 4.4 out of 5 stars
(32)
Marc Joseph New York Clark Road Mens Hands-Free Slip On Technology Chelsea Boot
$195.00
Rated 4 out of 5 stars
(1)
Stacy Adams Maury Men's Cap Toe Chelsea Boots
$145.00
Deer Stags Brock Jr Boys' Chelsea Boots
$65.00
Rated 4.5 out of 5 stars
(19)
Nunn Bush® 1912 Men's Leather Chelsea Boots
$115.00
Rated 4.8 out of 5 stars
(11)
Eastland Ida Women's Ankle Boots
$145.00
Rated 4.4 out of 5 stars
(75)
XTI Women's Heeled Chelsea Booties 144299
$79.80
$99.75
MUK LUKS Spike Madison Women's Chelsea Boots
$74.99
Rated 4.2 out of 5 stars
(8)
Marc Joseph New York Hudson Yards 2.0 Mens Hands-Free Slip On Technology Chelsea Boot
$195.00
Rated 5 out of 5 stars
(1)
Andrea Women's Animal Print Chelsea Boots 90773
$80.00
Top Rated
White Mountain Tahj Women's Lug Sole Booties
$68.99
Sale
$99.00 Reg.
Rated 5 out of 5 stars
(13)
Andrea Women's Biker Boots With Buckle 90792
$67.20
Rated 2 out of 5 stars
(1)
Stacy Adams Townsend Men's Plain Toe Chelsea Boots
$150.00
Journee Tekoa Women's Waterproof Rain Boots
$53.97
Sale
$89.99 Reg.
Rated 3.5 out of 5 stars
(78)
Coconuts by Matisse Effie Women's Ankle Boots
$168.00
Muck Muckster II Men's Waterproof Ankle Boots
$110.00
Rated 4.5 out of 5 stars
(46)
Rocket Dog Heyday Women's Platform Boots
$54.99
Sale
$69.95 Reg.
Rated 3.1 out of 5 stars
(10)
Bogs Holly Rain Zip Women's Waterproof Rain Boots
$95.00 - $105.00
Rated 3.7 out of 5 stars
(21)
Stacy Adams Isaacson Men's Chelsea Boots
$150.00
Bogs Kicker Men's Chelsea Rain Boots
$110.00
Rated 4.2 out of 5 stars
(5)
Deer Stags Zane Boys' Chelsea Boots
$60.00
Rated 5 out of 5 stars
(1)
Dockers® Ransom Men's Chelsea Boots
$80.00
Rated 3.6 out of 5 stars
(28)
Eastland Woodford Women's Boots
$100.00
Bogs Sweetpea II Women's Chelsea Rain Boots
$100.00
Rated 4.2 out of 5 stars
(204)
Stacy Adams Thompson Men's Elastic Lace Boots
$150.00
Triples Men's Chelsea Casual Boots Enzo - Real Leather
$37.60
$47.00
Rated 5 out of 5 stars
(1)
Round Toe Block Heels Chelsea Ankle Boots for Women
$77.42 - $81.49
$81.49
Select Styles on Sale
Rated 4 out of 5 stars
(1)
Top Rated
OshKosh B'gosh® Sebastian Toddler Boy Zip Ankle Boots
$23.97
Sale
$39.99 Reg.
Rated 4.9 out of 5 stars
(12)
XTI Women's Patent Leather Heeled Chelsea Booties 144277
$79.80
$93.10 - $99.75
Mykos Antoinette Women's Slip-On Ankle Boots
$119.99
Georgia Boots Eagle One Men's Waterproof Chelsea Work Boots
$170.00
Rated 4.2 out of 5 stars
(77)
Columbia Moritza Chelsea Women's Slip-On Ankle Boots
$100.00
Rated 3 out of 5 stars
(8)
Dockers® Tureen Men's Chelsea Boots
$85.00
Rated 1 out of 5 stars
(1)
Bogs Kicker Women's Chelsea Waterproof Rain Boot
$90.00
Rated 4.4 out of 5 stars
(5)
Stacy Adams Platt Men's Chelsea Boots
$110.00
totes Cirrus Men's Waterproof Chelsea Rain Boots
$60.00
Rated 4 out of 5 stars
(199)
Gino Vitale Men's Slip On Wing Tip Chelsea Boots
$89.99
XTI Women's Heeled Chelsea Booties 144521
$79.80 - $81.00
$93.10 - $133.00
Andrea Women's Leather Chelsea Boots 90568
$85.00
Georgia Boots Georgia Giant Revamp Men's Waterproof Chelsea Work Boots
$155.00
Rated 4.4 out of 5 stars
(24)
XTI Women's Chelsea Booties 144311
$79.80
$93.10
Rated 2 out of 5 stars
(1)
Georgia Boots Eagle One Men's Waterproof Steel Toe Chelsea Work Boots
$175.00
Rated 4.7 out of 5 stars
(48)
Bogs Women's Waterproof Rain Boots
$85.00
Rated 4.1 out of 5 stars
(44)
VANCE Hartwell Chelsea Men's Ankle Boots
$119.99
Rated 5 out of 5 stars
(4)
Andrea Women's Leather Chelsea Boots 63353
$89.00
VANCE Thorpe Men's Wingtip Slip-on Chelsea Boots
$109.99
Rated 4.2 out of 5 stars
(5)
Bogs Kicker Chelsea II Men's Waterproof Ankle Rain Boots
$95.00
Rated 4.4 out of 5 stars
(36)
VANCE Marshall Men's Chelsea Boots
$99.99
Rated 4.4 out of 5 stars
(25)
Georgia Boots Amp LT Men's Waterproof Steel Toe Chelsea Work Boots
$180.00
Rated 4.2 out of 5 stars
(28)
Seven Dials Marisah Women's Ankle Boots
$69.99
Rated 4.3 out of 5 stars
(14)
Georgia Boots Georgia Giant High Romeo Men's Waterproof Steel Toe Chelsea Work Boots
$155.00
Rated 4 out of 5 stars
(64)
Refresh Women's Suede Chelsea Booties 173027
$72.00
$90.00
XTI Women's Stretchy Chelsea Booties 144313
$79.80
$93.10
London Rag Jeffers Women's High Ankle Chelsea Boots
$68.99
Stacy Adams Brumley Men's Moc Toe Lace-Up Boots
$160.00
Andrea Women's Total Comfort Chelsea Booties 90547
$69.35
Refresh Women's Comfort Chelsea Suede Booties 173088
$81.00
$101.25
London Rag Yacht Women's Chelsea Boots
$66.99
Rated 2.7 out of 5 stars
(3)
Andrea Women's Total Comfort Chelsea Booties 90561
$73.60
Bogs Holly Women's Chelsea Rain Boots
$100.00
Rated 3.8 out of 5 stars
(106)
Bogs Sauvie II Chelsea Women's Waterproof Garden Clogs
$100.00
Rated 5 out of 5 stars
(4)
Refresh Women's Block Heel Chelsea Booties 172905
$79.80
$107.10
Women's Heeled Patent Leather Chelsea Booties By XTI 144315
$81.00
$108.95
Women's Chelsea Shinny Black Leather Boots By URBNKICKS
$419.00
Deer Stags Jameson Jr. Kid Boys' Chelsea Boots
$75.00
Rated 1 out of 5 stars
(2)
Bogs Women's Glitter Ankle Rain Boots
$80.00
Rated 4.4 out of 5 stars
(27)
Women's Chelsea Leather Loafer By URBNKICKS
$399.00
Women's Chelsea Two-Tone Leather Boots By URBNKICKS
$349.00
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