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Cole Haan Grand+ Ultra Men's Leathe…

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High-quality Material · Perfect Fit · Stylish · brown

Deer Stags Bangor Men's Chukka Boo…

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High-quality Material · Perfect Fit · Stylish · brown · leather

Georgia Boots Farm & Ranch Men's We…

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Koolaburra By UGG Braan Men's Sued…

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Propet Findley Men's Suede Chuk…

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Attractive Color · High-quality Material · Keeps feet warm · Perfect Fit · suede

Bearpaw Skye Women's Suede C…

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Clarks® Shacre Men's Suede Chuk…

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High-quality Material · Perfect Fit · Stylish · brown

Deer Stags Bangor Men's Chukka Boo…

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Eddie Bauer Men's Buckhorn Lace-Up …

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Clarks® Shacre Men's Leather Chu…

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Eastland Seneca Men's Chukka Boo…

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Men's Pyrenees Suede Chukka Boo…

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Mens Chukka Boots For Bunions, Male …

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L.L.Bean | Women's Stonington Chukk…

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Men's Sperry Top-Sider Authentic Ori…

34 % price drop

St. John's Bay Mens Acton Flat Heel Ch…

Clarks Mens Shacre Flat Heel Chukka B…

Clarks Bushacre Chukka Boot | Men'…

Skechers Men's Relaxed Fit: Respe…

St. John's Bay Mens Mills Flat Heel Chu…

34 % price drop

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St. John's Bay Mens Acton Flat Heel Ch…

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Clarks Mens Shacre Flat Heel Chukka B…

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Clarks Bushacre Chukka Boot | Men'…

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Skechers Men's Relaxed Fit: Respe…

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St. John's Bay Mens Mills Flat Heel Chu…

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High-quality Material · Perfect Fit · brown · suede

Roper Men's Sand Suede Gum Sole C…

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St. John's Bay Mens Mills Flat Heel Chu…

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L.L.Bean | Women's Stonington Chukk…

Roper Women's Suede Chukka Gu…

Skechers Men's Work: Kadmiel - Be…

Ralph Lauren Talan Suede Chukka Boo…

Bearpaw Women's Skye Chukka Boot…

Lace-Up Chukka Boot

High-quality Material · Perfect Fit · Stylish · brown · leather

Georgia Boot Men's Farm And Ranch C…

Clarks Bushacre 3 Chukka Boot | Men'…

Showing 1 - 36 out of 166 results for "comfortable chukka boots"
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  Johnston & Murphy Men's Upton Chu…
  $169.00
  M
  Macy's
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  Dr. Scholl's Men's Maplewood Chukk…
  $49.99
  $114.99
  1%cash back
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  Famous Footwear
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  Oboz Men's Burke Chukka Boots Griz…
  $140.00
  R
  REI
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  Oboz Men's Burke Chukka Boots Ad…
  $140.00
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  REI
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  Cole Haan Grand+ Ultra Men's Leath…
  $88.00
  $110.00
  K
  Kohl's
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  Oboz Men's Burke Chukka Boots Tro…
  $140.00
  R
  REI
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  Clarks Bushacre 3 Chukka Boot | Me…
  $89.99
  D
  DSW
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  Oboz Men's Burke Chukka Boots Tro…
  $140.00
  R
  REI
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  Nautica Men's Largo Chukka Boots - …
  $47.99
  $79.99
  M
  Macy's
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  Clarks Shepton Chukka Boot | Men's …
  $94.99
  D
  DSW
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  Handmade Allseason Lightweight Co…
  $59.97
  $120.00
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  Inspire Uplift
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  Handmade Allseason Lightweight Co…
  $59.97
  $120.00
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  Inspire Uplift
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  Timberland Men's Redwood Falls Wa…
  $135.00
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  REI
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  New York & Company Men's Hurley C…
  $29.99
  $70.00
  M
  Macy's
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  Sorel Men's Carson Chukka Waterpro…
  $160.00
  R
  REI
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  Clarks Men's Bushhacre 3 Chukka Bo…
  $89.99
  $109.99
  1%cash back
  ✕
  Cash back from Microsoft
  This is an offer from Microsoft. You'll get 1% cash back on this item from Microsoft Cashback. Learn more | Terms & conditions
  F
  Famous Footwear
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  Cole Haan Men's Berkshire Chukka B…
  $240.00
  B
  Bloomingdale's
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  Nautica Men's Cassius Chukka Boot…
  $80.00
  M
  Macy's
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  Handmade Allseason Lightweight Co…
  $59.97
  $120.00
  I
  Inspire Uplift
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  Dr. Scholl's Men's Chukka Boots - Ma…
  $54.98
  Q
  QVC
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  Oboz Men's Burke Chukka Boots Nim…
  $69.83
  $140.00
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  REI
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22. Saved
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  Nautica Men's Grandt Casual Chukk…
  $29.99
  $80.00
  M
  Macy's
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  Olukai Men's Papaku Chukka Boots …
  $130.00
  R
  REI
  Free shipping
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  Kiton Men's Tan Suede Vibram-Sole …
  $1,555.00
  B
  Bergdorf Goodman
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  Cole Haan Men's Grand Remix Chukk…
  $110.00
  $220.00
  M
  Macy's
  SALE
  Free shipping
26. Saved
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  Olukai Men's Papaku 'Ili Chukka Boot…
  $160.00
  R
  REI
  Free shipping
27. Saved
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  Eddie Bauer Men's Buckhorn Lace-U…
  $52.50
  $70.00
  K
  Kohl's
  SALE
  Free shipping
28. Saved
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  Handmade Allseason Lightweight Co…
  $59.97
  $120.00
  I
  Inspire Uplift
  SALE
  Free shipping
29. Saved
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  Deer Stags Bangor Men's Chukka Bo…
  $54.99
  $60.00
  K
  Kohl's
  SALE
  Free shipping
30. Saved
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  Olukai Men's Papaku 'Ili Chukka Boot…
  $160.00
  R
  REI
  Free shipping
31. Saved
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  Olukai Men's Papaku 'Ili Chukka Boot…
  $160.00
  R
  REI
  Free shipping
32. Saved
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  Clarks® Shacre Men's Suede Chukk…
  $110.00
  K
  Kohl's
  Free shipping
33. Saved
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  Florsheim Men's Vibe Plain Toe Chuk…
  $125.00
  M
  Macy's
  Free shipping
34. Saved
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  Olukai Men's Papaku Chukka Boots …
  $130.00
  R
  REI
  Free shipping
35. Saved
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  Thursday Boot Company Men's Sued…
  $160.00
  T
  Thursday Boot Company
36. Saved
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  Special Offer
  Clarks Bushacre Chukka Boot | Men'…
  $89.99
  D
  DSW
  Free shipping
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Free gift*
Clarks Shepton Chukka Boot | Men'…
$94.99
DSW
Ariat Men's Rebar Lift Chukka Work B…
$159.95
Boot Barn
Free shipping
Attractive Color · Comfortable · High-quality Material · Perfect Fit · suede
UGG® Women's Neumel Leather Sh…
$140.00
Ugg
4.5
·
10K+
Nunn Bush Mens Otto Pt Chukka Fla…
$110.00
JCPenney
5.0
·
1
B O C Livie Chukka Boot In Natural Nu…
$48.72

$64.97
Nordstrom Rack
High-quality Material · brown · suede
ROPER Mens Gum Sticker Chukka Ca…
$89.88
Amazon.com
4.5
·
235
Bates Men's Buckle Chukka Boots - Ro…
$189.95
Boot Barn
Free shipping
Free gift*
Dr. Scholl's Maplewood Chukk…
$64.99
DSW
Vionic Men's Uptown Chukka Bo…
$190.00
Vionic Shoes
Dr. Scholl's Men's Madison Chukka B…
$54.99

$114.99
Famous Footwear
Thorogood Men's Poromeric Acade…
$89.99
Boot Barn
Free shipping
Vionic Men's Uptown Chukka Bo…
$190.00
Vionic Shoes
Magellan Outdoors Men's Chukka Boo…
$39.99
Academy Sports + …
Men's Rebar Lift Chukka Work Boot…
$159.95
Ariat
Free shipping
30% Off*
Nike Woodside Chukka 2 Women'…
$130.00
Nike.com
Stetson Men's Chukka Casual Bo…
$264.99
Boot Barn
Free shipping
15% Off*
Men's Allagash Handsewn Chukk…
$159.00
L.L.Bean
UGG® Men's Burleigh Chukka S…
$160.00
Ugg
5.0
·
10
Clarks Mens Shacre Flat Heel Chukka B…
$66.00

$110.00
JCPenney
3.5
·
6
Attractive Color · High-quality Material · Perfect Fit · Stylish · Value for Money
Clarks Men's Bushhacre 3 Chuk…
$89.99

$109.99
Famous Footwear
4.5
·
10K+
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