Men's Ankle Boots

(123)

Limited-Time Special
BOSS by Hugo Boss
Men's Colby Leather Chelsea Slip On Boot
$119.40 (40% off)
$199.00
Bonus Offer With Purchase
JBU
Men's Kai Slip & Water-Resistant Chelsea Boot
Now $19.96 (75% off)
$80.00
$10 Star Money for $100
Limited-Time Special
Alfani
Men's Luka 2 Pull-On Chelsea Boots, Created for Macy's
$31.49 (55% off)
$69.99
$10 Star Money for $100
Limited-Time Special
Tommy Hilfiger
Men's Bage Lace Up Chukka Boots
$65.40 (40% off)
$109.00
$10 Star Money for $100
Limited-Time Special
Johnston & Murphy
Men's Boswell Chukka Boots
$99.00 (40% off)
$165.00
Bonus Offer With Purchase
Alfani
Men's Gregory Chukka Boot, Created for Macy's
Now $24.93 (64% off)
$69.99
$10 Star Money for $100
Limited-Time Special
Vintage Foundry Co
Men's Roberto Chelsea Boots
$150.00 (25% off)
$200.00
$10 Star Money for $100
Limited-Time Special
Madden Men
Men's Maxxin Mid Height Chelsea Boot
$40.50 (55% off)
$90.00
$10 Star Money for $100
Calvin Klein
Men's Fenwick Pull On Chelsea Boots
Now $73.93 (60% off)
$185.00
$10 Star Money for $100
Limited-Time Special
Reserved Footwear
Men's Glenn Ankle Boots
$54.99 (56% off)
$125.00
$10 Star Money for $100
Limited-Time Special
GUESS
Men's Dremmy Classic Slip-on Ankle Casual Boots
$54.50 (50% off)
$109.00
$10 Star Money for $100
Limited-Time Special
New York & Company
Men's Harrison Chelsea Boots
$34.99 (46% off)
$65.00
$10 Star Money for $100
Limited-Time Special
New York & Company
Men's Ankle Norman Boots
$29.99 (60% off)
$75.00
$10 Star Money for $100
Limited-Time Special
Clarks
Men's Bushacre 3 Boots
$72.00 (40% off)
$120.00
Bonus Offer With Purchase
Limited-Time Special
Reserved Footwear
Men's Gerard Ankle Boots
$54.99 (56% off)
$125.00
$10 Star Money for $100
Limited-Time Special
Rockport
Men's Cb Chukka Shoes
$112.00 (30% off)
$160.00
$10 Star Money for $100
Limited-Time Special
Territory
Men's Mack 2.0 Cap Moc Toe Ankle Boots
$119.99 (25% off)
$159.99
$10 Star Money for $100
Limited-Time Special
Reserved Footwear
Men's Neal Ankle Boots
$67.50 (25% off)
$90.00
$10 Star Money for $100
Limited-Time Special
Vintage Foundry Co
Men's Orson Chelsea Boots
$165.00 (25% off)
$220.00
$10 Star Money for $100
Limited-Time Special
Reserved Footwear
Men's Photon Chelsea Boots
$81.75 (25% off)
$109.00
$10 Star Money for $100
Limited-Time Special
Vance Co.
Men's Thorpe Tru Comfort Foam Wingtip Slip-On Chelsea Boots
$82.49 (25% off)
$109.99
$10 Star Money for $100
Limited-Time Special
Johnston & Murphy
Men's Marlow Chukka Boot
$225.25 (15% off)
$265.00
Bonus Offer With Purchase
Limited-Time Special
Anthony Veer
Men's Hills Suede Chelsea Boots
$52.49 - $56.24 (61-64% off)
$145.99
Bonus Offer With Purchase
Limited-Time Special
Reserved Footwear
Men's Vector Leather Work Boots
$97.50 (25% off)
$130.00
$10 Star Money for $100
Limited-Time Special
Territory
Men's Drifter Ankle Boots
$67.49 (55% off)
$149.99
$10 Star Money for $100
Limited-Time Special
Stacy Adams
Men's Finney Cap-Toe Chelsea Boot
$101.50 (30% off)
$145.00
Bonus Offer With Purchase
Limited-Time Special
Anthony Veer
Men's Rome Chelsea Boot
$296.09 (10% off)
$328.99
Bonus Offer With Purchase
Limited-Time Special
Territory
Men's Yellowstone Tru Comfort Foam Pull-On Water Resistant Chelsea Boots
$127.49 (25% off)
$169.99
$10 Star Money for $100
Limited-Time Special
Stacy Adams
Men's Maury Cap Toe Chelsea Boots
$91.00 (30% off)
$130.00
Bonus Offer With Purchase
Limited-Time Special
Vance Co.
Men's Fegan Tru Comfort Foam Cap Toe Lace-Up Ankle Boots
$82.49 (25% off)
$109.99
$10 Star Money for $100
Limited-Time Special
Vance Co.
Men's Langford Ankle Boots
$56.24 (25% off)
$74.99
$10 Star Money for $100
Limited-Time Special
Blake McKay
Men's Richmond Dress Chelsea Boots
$120.45 (27% off)
$165.00
$10 Star Money for $100
Limited-Time Special
New York & Company
Men's Parker Chelsea Boots
$36.00 (55% off)
$80.00
$10 Star Money for $100
Limited-Time Special
Reserved Footwear
Men's Ewan Chelsea Boots
$48.75 (25% off)
$65.00
$10 Star Money for $100
Limited-Time Special
Vintage Foundry Co
Men's Treyton Chukka Boots
$150.00 (25% off)
$200.00
$10 Star Money for $100
Limited-Time Special
Johnston & Murphy
Men's Upton Chukka Boots
$140.25 (15% off)
$165.00
Bonus Offer With Purchase
Limited-Time Special
Nunn Bush
Men's Ozark II Plain Toe Chukka
$79.99 (27% off)
$110.00
$10 Star Money for $100
Limited-Time Special
Vance Co.
Men's Derrick Ankle Boots
$82.49 (25% off)
$109.99
$10 Star Money for $100
Limited-Time Special
Vance Co.
Men's Waylon Tru Comfort Foam Pull-On Cap Toe Chelsea Boot
$89.99 (25% off)
$119.99
$10 Star Money for $100
Limited-Time Special
Reserved Footwear
Men's Quaid Chelsea Boots
$108.75 (25% off)
$145.00
$10 Star Money for $100
Limited-Time Special
Berrendo
Men's 6” Steel Toe Work Boots for Men – Pull-On Chelsea – Electrical Hazard – Oil and Slip Resistant
$111.65 (30% off)
$159.50
$10 Star Money for $100
Limited-Time Special
Nunn Bush
Men's Excavate Moc Toe Chelsea Boot
$59.99 (33% off)
$90.00
$10 Star Money for $100
Limited-Time Special
Reserved Footwear
Men's Ryder Chelsea Boots
$44.10 - $73.50 (25-55% off)
$98.00
$10 Star Money for $100
Limited-Time Special
Johnston & Murphy
Men's Gregory Chukka Boot
$208.25 (15% off)
$245.00
Bonus Offer With Purchase
Limited-Time Special
PAZSTOR
Men's Premium Comfort Leather Low Ankle Boots
$65.80 - $76.30 (30% off)
$94.00 - $109.00
$10 Star Money for $100
Limited-Time Special
Territory
Men's Axel Ankle Boot
$62.55 (55% off)
$139.01
$10 Star Money for $100
Limited-Time Special
RUSH Gordon Rush
Men's Logan Dress Casual Chelsea Boot
$45.90 (66% off)
$135.00
$10 Star Money for $100
Limited-Time Special
Nautica
Men's Vega Chukka Boot
$42.00 (40% off)
$70.00
$10 Star Money for $100
Limited-Time Special
Carlos by Carlos Santana
Men's Durango Chelsea Boots
$143.09 (10% off)
$158.99
Bonus Offer With Purchase
Limited-Time Special
Barbour
Men's Patton Chelsea Boot
$108.00 (55% off)
$240.00
Bonus Offer With Purchase
Limited-Time Special
Sorel
Men's Carson Waterproof Suede Chelsea Boot
$69.75 (55% off)
$155.00
Bonus Offer With Purchase
Limited-Time Special
Reserved Footwear
Men's Maksim Leather Chelsea Boots
$112.50 (25% off)
$150.00
$10 Star Money for $100
Limited-Time Special
Rockport
Men's Classic Break Chukka Boots
$112.00 (30% off)
$160.00
$10 Star Money for $100
Limited-Time Special
Territory
Men's Bridger Ankle Boot
$45.00 - $75.00 (25-55% off)
$100.00
$10 Star Money for $100
Limited-Time Special
Dockers
Men's Dee Casual Chukka Boot
$38.25 (55% off)
$85.00
$10 Star Money for $100
Limited-Time Special
Vance Co.
Men's Virgil Tru Comfort Foam Wingtip Lace-Up Ankle Boots
$97.49 (25% off)
$129.99
$10 Star Money for $100
Limited-Time Special
Taft 365
Men's Model 004 Wedge Sole Lace-Up Ankle Boots
$89.99 (55% off)
$199.99
Bonus Offer With Purchase
Limited-Time Special
Vintage Foundry Co
Men's Blaise Chelsea Boot
$201.75 (25% off)
$269.00
$10 Star Money for $100
Limited-Time Special
XTI
Ankle Boots For Men
$56.00 (30% off)
$80.00
$10 Star Money for $100
Limited-Time Special
XRAY
Footwear Men's Griffin Chukka Boots
$60.00 (25% off)
$80.00
$10 Star Money for $100

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