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Men's Chelsea & Chukka Boots

85 products

Sort by:Featured

Featured

New Arrival

Price - Low to High

Price - High to Low

6.5

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7.5

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9.5

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12

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Medium(80)

Wide(21)

Extra Wide(6)

Extra Extra Wide(1)

Extra Extra Extra Wide(1)

Extra Extra Extra Extra Wide(2)

Ariat(14)

Clarks(1)

Durango(3)

Frye(2)

Georgia Boots(3)

Johnston & Murphy(6)

Justin Boots(2)

Laredo(2)

Lee(1)

Lugz(8)

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Chukka(50)

Chelsea(35)

Pull on(16)

Lace Up(13)

Rain(1)

Brown(55)

Black(18)

Beige(8)

Grey(3)

Blue(1)

Comfort Technology(31)

E.V.A.(26)

Removable Insole(21)

Ortholite(10)

Slip Resistant(10)

Lightweight(9)

Breathable(7)

Waterproof(6)

Moisture Wicking(5)

Non-Marking Sole(4)

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Flat(26)

Low Heel 1in-2in(54)

Ankle(83)

Animal Print(2)

Ostrich(2)

Embossed(1)

Embroidery(1)

Soft(2)

Round(58)

Square(17)

Moc(8)

Cap(1)

Plain(1)

$20 to $40(1)

$40 to $60(15)

$60 to $80(3)

$80 to $100(14)

$100 to $150(38)

$150 to $200(11)

$200 to $300(3)

Up to 30% off(23)

Up to 50% off(10)

Up to 70% off(10)

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Size: 7

7

8

8.5

9

9.5

10

10.5

11

12

Width: Wide

Wide

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Durango | Mens\ \ Shyloh Square Toe Chelsea Boots\ \ $125.50

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Size: 7.5

7.5

8

8.5

9

9.5

10

10.5

11

11.5

12

13

14

Width: Medium

Medium

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Roper | Mens\ \ Magnum Western Chelsea Boots\ \ $99.99

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Size: 8.5

8.5

9

9.5

10

10.5

11

11.5

12

13

8

Width: Medium

Medium

Add to cart

Ariat | Mens\ \ Clean Country Moc Toe Chukka Boots\ \ $139.95

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Size: 10.5

10.5

7

8

8.5

9

9.5

10

11

11.5

12

13

Width: Wide

Wide

Medium

Add to cart

Durango | Mens\ \ Shyloh Square Toe Chelsea Boots\ \ $125.50

\ \

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Size: 7

7

8

9

10

11

12

13

14

15

Width: Medium

Medium

Add to cart

Muck Boot | Mens\ \ Rainscape Pull On Rain Boots\ \ $105.00

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Size: 8.5

8.5

9.5

10

8

10.5

11

11.5

12

13

Width: Medium

Medium

Add to cart

Frye | Mens\ \ Paul Chukka Lite Lace Up Boots\ \ $198.00

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Size: 8

8

8.5

9

9.5

10

10.5

11

11.5

12

13

Width: Medium

Medium

Add to cart

Ariat | Mens\ \ Spitfire Moc Toe Chukka Boots\ \ $129.95

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Size: 8

8

8.5

9

9.5

10

10.5

11

11.5

12

13

7

7.5

Width: Medium

Medium

Wide

Add to cart

Durango | Mens\ \ Shyloh Square Toe Chelsea Boots\ \ $125.50

\ \

Add to cart

Size: 8

8

8.5

9

9.5

10

10.5

11

13

Width: Medium

Medium

Add to cart

Ariat | Mens\ \ Booker Ultra Square Toe Chelsea Boots\ \ $149.95

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Size: 8

8

8.5

9

9.5

10

10.5

11

11.5

12

13

Width: Medium

Medium

Add to cart

Ariat | Mens\ \ Hybrid Low Boy Wide Square Toe Chelsea Boots\ \ $159.95

\ \

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Size: 9.5

9.5

10

10.5

11

11.5

12

13

8

8.5

9

Width: Wide

Wide

Medium

Add to cart

Ariat | Mens\ \ Booker Ultra Square Toe Chelsea Boots\ \ $149.95

\ \

Add to cart

Size: 7.5

7.5

8

8.5

9.5

10

11

6.5

9

10.5

11.5

12

13

Width: Wide

Wide

Add to cart

Lugz | Mens\ \ Fringe Moc Toe Chukka Boots\ \ $59.99

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Size: 6.5

6.5

7

7.5

8

8.5

9

9.5

10

10.5

11

Width: Wide

Wide

Add to cart

Lugz | Mens\ \ Fringe Moc Toe Chukka Boots\ \ $59.99

\ \

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Size: 7.5

7.5

8

8.5

9

9.5

10

10.5

11

11.5

12

13

Width: Medium

Medium

Add to cart

Roper | Mens\ \ Clearcut Round Toe Chukka Boots\ \ $99.99

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Size: 8

8

8.5

9

9.5

10

10.5

11

11.5

12

Width: Medium

Medium

Add to cart

Roper | Mens\ \ Clearcut Round Toe Chukka Boots\ \ $144.99

\ \

Add to cart

Size: 7

7

7.5

8

8.5

9

9.5

10

10.5

11

11.5

12

13

Width: Medium

Medium

Add to cart

Roper | Mens\ \ Stirrup Ostrich Print Moc Toe Chukka Boots\ \ $144.99

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Size: 8

8

8.5

9

9.5

10

11

11.5

12

13

Width: Medium

Medium

Add to cart

Olukai | Mens\ \ Papaku ‘ili Chukka Boots\ \ $159.95

\ \

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Size: 7

7

8

8.5

9

9.5

10

10.5

11

11.5

7.5

13

Width: Medium

Medium

Add to cart

Roper | Mens\ \ Clearcut Round Toe Chukka Boots\ \ $129.99

\ \

Add to cart

Size: 7.5

7.5

9.5

10

10.5

11

12

13

8

8.5

7

9

Width: Medium

Medium

Add to cart

Lugz | Mens\ \ Fringe Round Toe Chukka Boots\ \ $59.99

\ \

Add to cart

Size: 7

7

7.5

8

8.5

9

9.5

10

10.5

11

11.5

12

13

14

Width: Medium

Medium

Add to cart

Tony Lama | Mens\ \ Estancia Lace Up Moc Toe Chukka Boots\ \ $110.46

\ \

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Size: 7

7

7.5

8

8.5

9

9.5

10

10.5

11

11.5

12

13

14

Width: Medium

Medium

Add to cart

Tony Lama | Mens\ \ Estancia Lace Up Moc Toe Chukka Boots\ \ $110.46

\ \

Add to cart

Size: 7

7

7.5

8

8.5

9

9.5

10

10.5

11

11.5

12

13

14

Width: Medium

Medium

Add to cart

Tony Lama | Mens\ \ Estancia Lace Up Moc Toe Chukka Boots\ \ $103.46

\ \

Add to cart

Size: 7

7

7.5

8

8.5

9

9.5

10

10.5

11

12

13

Width: Medium

Medium

Add to cart

Roper | Mens\ \ Clearcut Round Toe Chukka Boots\ \ $124.99

\ \

Add to cart

Size: 8

8

8.5

9

9.5

10

10.5

11

11.5

12

13

Width: Medium

Medium

Add to cart

Ariat | Mens\ \ Hybrid Low Boy Square Toe Chelsea Boots\ \ $159.95

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