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  • Deer Stags Rockland Men's Chelsea Boots
    $64.00 with code MYFAMILY20 Promo details.
    $80.00 Reg.

    Deer Stags Rockland Men's Chelsea Boots

    (49)
    Black Black Redwood Dark Brown
  • Vance Salter Men's Casual Chelsea Boots
    $65.99 with code MYFAMILY20 Promo details.
    $82.49 sale $109.99 Reg.

    Vance Salter Men's Casual Chelsea Boots

    Walnut Black
  • VANCE Marshall Men's Chelsea Boots
    $59.99 with code MYFAMILY20 Promo details.
    $74.99 sale $99.99 Reg.

    VANCE Marshall Men's Chelsea Boots

    (22)
    Taupe Gray Black
  • Eddie Bauer Men's Norwalk Chelsea Boots
    $63.75 sale
    $75.00 Reg.

    Eddie Bauer Men's Norwalk Chelsea Boots

    (2)
  • Nunn Bush® Otis II Men's Leather Chelsea Boots
    $91.99 with code MYFAMILY20 Promo details.
    $114.99 sale $120.00 Reg.

    Nunn Bush® Otis II Men's Leather Chelsea Boots

    (4)
    Tan Brown Crazy Horse Black Tumbled
  • Nunn Bush® Excavate Men's Moc Toe Chelsea Boots
    $71.99 with code MYFAMILY20 Promo details.
    $89.99 sale $95.00 Reg.

    Nunn Bush® Excavate Men's Moc Toe Chelsea Boots

    (11)
    Brown Black
  • Dockers® Ransom Men's Chelsea Boots
    $80.00

    Dockers® Ransom Men's Chelsea Boots

    (28)
  • New York & Company Parker Chelsea Men's Boots
    $65.00

    New York & Company Parker Chelsea Men's Boots

    Brown Black
  • VANCE Garrett Men's Chelsea Boots
    $59.99 with code MYFAMILY20 Promo details.
    $74.99 sale $99.99 Reg.

    VANCE Garrett Men's Chelsea Boots

    (14)
    Brown Black
  • Dockers® Townsend Men's Chelsea Boots
    $85.00

    Dockers® Townsend Men's Chelsea Boots

    (5)
  • Nunn Bush® Karnak Men's Plain Toe Chelsea Slip-On Boots
    $91.99 with code MYFAMILY20 Promo details.
    $114.99 sale $120.00

    Nunn Bush® Karnak Men's Plain Toe Chelsea Slip-On Boots

    Tan Crazy Horse Black Tumbled
  • Men's Caterpillar Striver Chelsea Steel Toe Waterproof Work Boots
    $88.00 with code MYFAMILY20 Promo details.
    $110.00 Reg.

    Men's Caterpillar Striver Chelsea Steel Toe Waterproof Work Boots

    (4)
  • Top Rated
    Eastland Daily Double Men's Leather Chelsea Boots
    $125.00

    Eastland Daily Double Men's Leather Chelsea Boots

    (11)
  • Propet Troy Men's Leather Ankle Boots
    $111.96 with code MYFAMILY20 Promo details.
    $139.95 Reg.

    Propet Troy Men's Leather Ankle Boots

    (21)
  • Deer Stags Brayden Men's Dress Chelsea Boots
    $52.00 with code MYFAMILY20 Promo details.
    $65.00 Reg.

    Deer Stags Brayden Men's Dress Chelsea Boots

    (6)
    Brown Black
  • Reserved Footwear Ryder Men's Chelsea Boots
    $52.00 with code MYFAMILY20 Promo details.
    $65.00 Reg.

    Reserved Footwear Ryder Men's Chelsea Boots

    (9)
  • totes Cirrus Men's Waterproof Chelsea Rain Boots
    $48.00 with code MYFAMILY20 Promo details.
    $60.00 Reg.

    totes Cirrus Men's Waterproof Chelsea Rain Boots

    (192)
  • Georgia Boots Georgia Giant Revamp Men's Waterproof Chelsea Work Boots
    $141.00 - $155.00

    Georgia Boots Georgia Giant Revamp Men's Waterproof Chelsea Work Boots

    (24)
  • Georgia Boots Eagle One Men's Waterproof Steel Toe Chelsea Work Boots
    $172.00 - $175.00

    Georgia Boots Eagle One Men's Waterproof Steel Toe Chelsea Work Boots

    (48)
  • Deer Stags Argos Men's Chelsea Boots
    $48.00 with code MYFAMILY20 Promo details.
    $60.00 Reg.

    Deer Stags Argos Men's Chelsea Boots

    (45)
  • Bogs Kicker Chelsea II Men's Waterproof Ankle Rain Boots
    $85.00 - $95.00

    Bogs Kicker Chelsea II Men's Waterproof Ankle Rain Boots

    (33)
    Gray Black
  • Georgia Boots Amp LT Men's Waterproof Steel Toe Chelsea Work Boots
    $165.00 - $180.00

    Georgia Boots Amp LT Men's Waterproof Steel Toe Chelsea Work Boots

    (26)
  • Muck Muckster II Men's Waterproof Ankle Boots
    $110.00

    Muck Muckster II Men's Waterproof Ankle Boots

    (33)
  • Gino Vitale Men's Wingtip Brogue Two-Tone Chelsea Boots
    $89.99

    Gino Vitale Men's Wingtip Brogue Two-Tone Chelsea Boots

    Black Black Wine Navy Gray Black Brown Brown
  • Nunn Bush® 1912 Men's Leather Chelsea Boots
    $87.99 with code MYFAMILY20 Promo details.
    $109.99 sale $115.00 Reg.

    Nunn Bush® 1912 Men's Leather Chelsea Boots

    (11)
  • Propet Tyler Men's Waterproof Ankle Boots
    $111.96 with code MYFAMILY20 Promo details.
    $139.95 Reg.

    Propet Tyler Men's Waterproof Ankle Boots

    (15)
  • Dockers® Tureen Men's Chelsea Boots
    $85.00

    Dockers® Tureen Men's Chelsea Boots

    (1)
  • Georgia Boots AMP LT Men's Wedge Chelsea Work Boots
    $155.00 - $170.00

    Georgia Boots AMP LT Men's Wedge Chelsea Work Boots

    (29)
  • VANCE Waylon Men's Pull-On Chelsea Boots
    $71.99 with code MYFAMILY20 Promo details.
    $89.99 sale $119.99 Reg.

    VANCE Waylon Men's Pull-On Chelsea Boots

    (5)
    Brown Gray
  • Deer Stags Jameson S.U.P.R.O INSIDE Men’s Chelsea Boots
    $75.99 - $91.99 with code MYFAMILY20 Promo details.
    $94.99 - $114.99 sale $100.00 - $120.00 Reg.

    Deer Stags Jameson S.U.P.R.O INSIDE Men’s Chelsea Boots

    Brown Black
  • VANCE Thorpe Men's Tru Comfort Foam Wingtip Slip-on Chelsea Boots
    $65.99 with code MYFAMILY20 Promo details.
    $82.49 sale $109.99 Reg.

    VANCE Thorpe Men's Tru Comfort Foam Wingtip Slip-on Chelsea Boots

    (4)
    Brown Navy Gray
  • VANCE Hartwell Chelsea Men's Ankle Boots
    $71.99 with code MYFAMILY20 Promo details.
    $89.99 sale $119.99 Reg.

    VANCE Hartwell Chelsea Men's Ankle Boots

    (3)
    Brown Navy Black
  • Georgia Boots Wedge Men's Waterproof Chelsea Work Boots
    $160.00 - $175.00

    Georgia Boots Wedge Men's Waterproof Chelsea Work Boots

    (32)
  • Nunn Bush® Trekker Men's Moc Toe Chelsea Boots
    $63.99 with code MYFAMILY20 Promo details.
    $79.99 sale $85.00 Reg.

    Nunn Bush® Trekker Men's Moc Toe Chelsea Boots

  • New York & Company Harrison Chelsea Men's Boots
    $54.00

    New York & Company Harrison Chelsea Men's Boots

    (5)
  • Georgia Boots Georgia Giant High Romeo Men's Waterproof Steel Toe Chelsea Work Boots
    $138.00 - $155.00

    Georgia Boots Georgia Giant High Romeo Men's Waterproof Steel Toe Chelsea Work Boots

    (63)
  • Georgia Boots Eagle One Men's Waterproof Chelsea Work Boots
    $167.00 - $170.00

    Georgia Boots Eagle One Men's Waterproof Chelsea Work Boots

    (73)
  • Dockers® Ettrick Men's Chelsea Boots
    $85.00

    Dockers® Ettrick Men's Chelsea Boots

  • Eastland Daily Double Men's Chelsea Boots
    $125.00

    Eastland Daily Double Men's Chelsea Boots

    (5)
  • Bogs Kicker Men's Chelsea Rain Boots
    $110.00

    Bogs Kicker Men's Chelsea Rain Boots

    (33)
  • Gino Vitale Men's Slip On Wing Tip Chelsea Boots
    $89.99

    Gino Vitale Men's Slip On Wing Tip Chelsea Boots

    Light Brown Red Blue Black
  • Bogs Sauvie Chelsea II Men's Waterproof Boots
    $110.00

    Bogs Sauvie Chelsea II Men's Waterproof Boots

    (244)
  • Reserved Footwear Photon Men's Suede Chelsea Boots
    $87.20 with code MYFAMILY20 Promo details.
    $109.00 Reg.

    Reserved Footwear Photon Men's Suede Chelsea Boots