Shop men's chukka boots

Sponsored
About our ads
$29.99
$100.00
St. John's Bay Mens Acton Flat Heel Chukka Boots | Brown | Regular 10 1/2 | Boots Chukka Boots | Memory Foam | Holiday Gifts
JCPenney
35
70% off
$29.99
$100.00
St. John's Bay Mens Acton Flat Heel Chukka Boots | Brown | Regular 10 1/2 | Boots Chukka Boots | Memory Foam | Holiday Gifts
JCPenney
35
$90.00
Cole Haan Chester Chukka - Brown / Men'scasual - Size 11
Shoes for Crews
$90.00
Cole Haan Chester Chukka - Brown / Men'scasual - Size 11
Shoes for Crews
$110.00
Skechers Men's Hands Free Slip-Ins John Deere Waterproof: Respected - Tanzier Boots | Size 14.0 | Olive/Brown | Leather/Synthetic
Skechers USA
2
$110.00
Skechers Men's Hands Free Slip-Ins John Deere Waterproof: Respected - Tanzier Boots | Size 14.0 | Olive/Brown | Leather/Synthetic
Skechers USA
2
$105.00
Skechers Men's Relaxed Fit: Respected - Boswell Boots | Size 8.5 | Brown | Leather/Synthetic
Skechers USA
877
$105.00
Skechers Men's Relaxed Fit: Respected - Boswell Boots | Size 8.5 | Brown | Leather/Synthetic
Skechers USA
877
$35.00
MOZO Speakeasy Chukka 4SG - Brown / Men's4-Season Grip - Size 11
Shoes for Crews
$35.00
MOZO Speakeasy Chukka 4SG - Brown / Men's4-Season Grip - Size 11
Shoes for Crews
$26.99
$90.00
St. John's Bay Mens Mills Flat Heel Chukka Boots | Black | Regular 8 1/2 | Boots Chukka Boots | Memory Foam
JCPenney
70% off
$26.99
$90.00
St. John's Bay Mens Mills Flat Heel Chukka Boots | Black | Regular 8 1/2 | Boots Chukka Boots | Memory Foam
JCPenney
$110.00
Skechers Men's Hands Free Slip-Ins Relaxed Fit: Pollard - Waylon Boots | Size 11.0 | Red/Brown | Leather/Synthetic/Metal
Skechers USA
2
$110.00
Skechers Men's Hands Free Slip-Ins Relaxed Fit: Pollard - Waylon Boots | Size 11.0 | Red/Brown | Leather/Synthetic/Metal
Skechers USA
2
$129.99
Redhead Series 61 Chukka Boots For Men - Russet - 11m
Cabela's
$129.99
Redhead Series 61 Chukka Boots For Men - Russet - 11m
Cabela's
$1,320.00
Gucci Men's Sylke Suede Bit Lug-Sole Chukka Boots, Nocciola, Men's, 11, Boots Chukka & Desert Boots
Neiman Marcus
1
Free shipping
$1,320.00
Gucci Men's Sylke Suede Bit Lug-Sole Chukka Boots, Nocciola, Men's, 11, Boots Chukka & Desert Boots
Neiman Marcus
1
$140.00
Men's Heritage Suede Chukka Boot In Whiskey, Size 10, Suede Leather By Quince
Quince
Free shipping
$140.00
Men's Heritage Suede Chukka Boot In Whiskey, Size 10, Suede Leather By Quince
Quince
Free shipping
$122.98
MOZO Speakeasy Chukka 4SG - Black / Men's4-Season Grip - Size 9.5
Shoes for Crews
$122.98
MOZO Speakeasy Chukka 4SG - Black / Men's4-Season Grip - Size 9.5
Shoes for Crews
$149.99
Timberland Britton Chukka Boot | Men's | Dark Brown | Size 9 | Boots | Chukka
DSW
Free shipping
$149.99
Timberland Britton Chukka Boot | Men's | Dark Brown | Size 9 | Boots | Chukka
DSW
Free shipping
$140.00
Men's Heritage Suede Chukka Boot In Charcoal, Size 10.5, Suede Leather By Quince
Quince
Free shipping
$140.00
Men's Heritage Suede Chukka Boot In Charcoal, Size 10.5, Suede Leather By Quince
Quince
Free shipping
$319.00
Suede Chukka Boots - Tobacco Brown Size 10 By Charles Tyrwhitt
Charles Tyrwhitt
$319.00
Suede Chukka Boots - Tobacco Brown Size 10 By Charles Tyrwhitt
Charles Tyrwhitt
$890.00
Santoni Men's Gregory Suede Chukka Boots, Brown, Men's, 9, Boots Chukka & Desert Boots
Neiman Marcus
Free shipping
$890.00
Santoni Men's Gregory Suede Chukka Boots, Brown, Men's, 9, Boots Chukka & Desert Boots
Neiman Marcus
Free shipping
$134.99
Timberland Redwood Falls Chukka Boot | Men's | Dark Brown | Size 10 | Boots | Lug
DSW
Free shipping
$134.99
Timberland Redwood Falls Chukka Boot | Men's | Dark Brown | Size 10 | Boots | Lug
DSW
Free shipping
$1,320.00
Gucci Men's Sylke Suede Bit Lug-Sole Chukka Boots, Oatmeal, Men's, 10D, Boots Chukka & Desert Boots
Neiman Marcus
1
Free shipping
$1,320.00
Gucci Men's Sylke Suede Bit Lug-Sole Chukka Boots, Oatmeal, Men's, 10D, Boots Chukka & Desert Boots
Neiman Marcus
1
$99.00
Clarks - Mens - Walpath Chukka Waterproof Leather - 8.5 - Black
ClarksUSA.com
$99.00
Clarks - Mens - Walpath Chukka Waterproof Leather - 8.5 - Black
ClarksUSA.com
$52.77
$110.00
Clarks® Shacre Men's Suede Chukka Boots, Size: 9, Black Suede
Kohl's
3K+
Free shipping
52% off
$52.77
$110.00
Clarks® Shacre Men's Suede Chukka Boots, Size: 9, Black Suede
Kohl's
3K+
$245.00
Gordon Rush Men's Austin Dress Three-Eye Chukka Boots - Black - Size 13
Macy's
Free shipping
$245.00
Gordon Rush Men's Austin Dress Three-Eye Chukka Boots - Black - Size 13
Macy's
Free shipping
$1,150.00
Prada Suede Chukka Boots, Man, Dark Brown, Size 6
Prada
Free shipping
$1,150.00
Prada Suede Chukka Boots, Man, Dark Brown, Size 6
Prada
Free shipping
$99.00
Clarks - Mens - Walpath Chukka Waterproof Leather - 8.5 - Brown
ClarksUSA.com
$99.00
Clarks - Mens - Walpath Chukka Waterproof Leather - 8.5 - Brown
ClarksUSA.com
$160.00
Tommy Bahama Men's Olukai Papaku 'Ili Chukka Boots - Tan - Size 11
Tommy Bahama
112
$160.00
Tommy Bahama Men's Olukai Papaku 'Ili Chukka Boots - Tan - Size 11
Tommy Bahama
112
$89.99
World Wide Sportsman Blue Water Waterproof Chukka Boots For Men - Dark Brown - 10.5 m
Cabela's
$89.99
World Wide Sportsman Blue Water Waterproof Chukka Boots For Men - Dark Brown - 10.5 m
Cabela's
$54.99
Men's Beige Faux Suede Chukka Boots With Lace-Up Design - Casual Lightweight Ankle Boots For Everyday Wear
LightIntheBox.com
$54.99
Men's Beige Faux Suede Chukka Boots With Lace-Up Design - Casual Lightweight Ankle Boots For Everyday Wear
LightIntheBox.com
$160.00
Tommy Bahama Men's Olukai Papaku 'Ili Chukka Boots - Graphite - Size 10
Tommy Bahama
$160.00
Tommy Bahama Men's Olukai Papaku 'Ili Chukka Boots - Graphite - Size 10
Tommy Bahama
$23.99
$59.99
Sonoma Goods For Life® Hommer Freer Men's Comfort Chukka Boots, Size: 9.5, Black
Kohl's
60% off
$23.99
$59.99
Sonoma Goods For Life® Hommer Freer Men's Comfort Chukka Boots, Size: 9.5, Black
Kohl's
$265.00
Gordon Rush Men's Austin Dress Three-Eye Chukka Boots - Espresso - Size 9.5
Macy's
Free shipping
$265.00
Gordon Rush Men's Austin Dress Three-Eye Chukka Boots - Espresso - Size 9.5
Macy's
Free shipping
$269.99
Men's Weekender Chukka In Chocolate Muleskinner Leather 3315 | Red Wing Heritage
Red Wing
$269.99
Men's Weekender Chukka In Chocolate Muleskinner Leather 3315 | Red Wing Heritage
Red Wing
$79.20
$110.00
Clarks® Shacre Men's Leather Chukka Boots, Size: 9, Beeswax
Kohl's
23
Free shipping
28% off
$79.20
$110.00
Clarks® Shacre Men's Leather Chukka Boots, Size: 9, Beeswax
Kohl's
23
$84.99
Heydude Men's Bradley Chukka Classic Lace Up Boots (Tan) - Size 8.0 m
Famous Footwear
Free shipping
$84.99
Heydude Men's Bradley Chukka Classic Lace Up Boots (Tan) - Size 8.0 m
Famous Footwear
Free shipping
$99.99
Timberland Westmore Chukka Boot | Men's | Dark Brown | Size 12 | Boots | Moc Toe
DSW
Free shipping
$99.99
Timberland Westmore Chukka Boot | Men's | Dark Brown | Size 12 | Boots | Moc Toe
DSW
Free shipping
$104.99
$139.99
Carhartt Men's Wedge Plain Toe Chukka | Dark Brown | 13 m
Carhartt
2
25% off
$104.99
$139.99
Carhartt Men's Wedge Plain Toe Chukka | Dark Brown | 13 m
Carhartt
2
$160.00
Olukai Papaku 'Ili Waterproof Chukka Boot In Tan /Tan At Nordstrom, Size 11
Nordstrom
112
$160.00
Olukai Papaku 'Ili Waterproof Chukka Boot In Tan /Tan At Nordstrom, Size 11
Nordstrom
112
$105.00
Men's Jos. A. Bank Chukka Boots At Jos. A. Bank, Brown, Size 11 D Width - Shoes
Jos. A. Bank Clothiers, Inc.
$105.00
Men's Jos. A. Bank Chukka Boots At Jos. A. Bank, Brown, Size 11 D Width - Shoes
Jos. A. Bank Clothiers, Inc.
$49.99
Magellan Outdoors Men's Chukka Boot Brown, 10 - Men's Casual At Academy Sports
Academy Sports + Outdoors
$49.99
Magellan Outdoors Men's Chukka Boot Brown, 10 - Men's Casual At Academy Sports
Academy Sports + Outdoors
Men - Official Trailer (2022) Alex Garland, Jessie Buckley, Rory Kinnear | A24
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Check out the trailer for Men, the upcoming horror film written and directed by Alex Garland. Men stars Jessie Buckley, Rory Kinnear, and Paapa Essiedu. In the aftermath of a personal tragedy, Harper (Jessie Buckley) retreats alone to the beautiful English countryside, hoping to have found a place to heal. But someone or something from the ...
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Shop men's chukka boots

Sponsored
About our ads
$149.99
Timberland Britton Chukka Boot | Men's | Dark Brown | Size 9 | Boots | Chukka
DSW
Free shipping
$149.99
Timberland Britton Chukka Boot | Men's | Dark Brown | Size 9 | Boots | Chukka
DSW
$140.00
Men's Heritage Suede Chukka Boot In Charcoal, Size 10.5, Suede Leather By Quince
Quince
Free shipping
$140.00
Men's Heritage Suede Chukka Boot In Charcoal, Size 10.5, Suede Leather By Quince
Quince
$319.00
Suede Chukka Boots - Tobacco Brown Size 10 By Charles Tyrwhitt
Charles Tyrwhitt
$319.00
Suede Chukka Boots - Tobacco Brown Size 10 By Charles Tyrwhitt
Charles Tyrwhitt
$890.00
Santoni Men's Gregory Suede Chukka Boots, Brown, Men's, 9, Boots Chukka & Desert Boots
Neiman Marcus
Free shipping
$890.00
Santoni Men's Gregory Suede Chukka Boots, Brown, Men's, 9, Boots Chukka & Desert Boots
Neiman Marcus
$134.99
Timberland Redwood Falls Chukka Boot | Men's | Dark Brown | Size 10 | Boots | Lug
DSW
Free shipping
$134.99
Timberland Redwood Falls Chukka Boot | Men's | Dark Brown | Size 10 | Boots | Lug
DSW
$1,320.00
Gucci Men's Sylke Suede Bit Lug-Sole Chukka Boots, Oatmeal, Men's, 10D, Boots Chukka & Desert Boots
Neiman Marcus
1
Free shipping
$1,320.00
Gucci Men's Sylke Suede Bit Lug-Sole Chukka Boots, Oatmeal, Men's, 10D, Boots Chukka & Desert Boots
Neiman Marcus
$99.00
Clarks - Mens - Walpath Chukka Waterproof Leather - 8.5 - Black
ClarksUSA.com
$99.00
Clarks - Mens - Walpath Chukka Waterproof Leather - 8.5 - Black
ClarksUSA.com
$52.77
$110.00
Clarks® Shacre Men's Suede Chukka Boots, Size: 9, Black Suede
Kohl's
3K+
Free shipping
52% off
$52.77
$110.00
Clarks® Shacre Men's Suede Chukka Boots, Size: 9, Black Suede
Kohl's
$245.00
Gordon Rush Men's Austin Dress Three-Eye Chukka Boots - Black - Size 13
Macy's
Free shipping
$245.00
Gordon Rush Men's Austin Dress Three-Eye Chukka Boots - Black - Size 13
Macy's
$1,150.00
Prada Suede Chukka Boots, Man, Dark Brown, Size 6
Prada
Free shipping
$1,150.00
Prada Suede Chukka Boots, Man, Dark Brown, Size 6
Prada
$99.00
Clarks - Mens - Walpath Chukka Waterproof Leather - 8.5 - Brown
ClarksUSA.com
$99.00
Clarks - Mens - Walpath Chukka Waterproof Leather - 8.5 - Brown
ClarksUSA.com
$160.00
Tommy Bahama Men's Olukai Papaku 'Ili Chukka Boots - Tan - Size 11
Tommy Bahama
112
$160.00
Tommy Bahama Men's Olukai Papaku 'Ili Chukka Boots - Tan - Size 11
Tommy Bahama
$89.99
World Wide Sportsman Blue Water Waterproof Chukka Boots For Men - Dark Brown - 10.5 m
Cabela's
$89.99
World Wide Sportsman Blue Water Waterproof Chukka Boots For Men - Dark Brown - 10.5 m
Cabela's
$54.99
Men's Beige Faux Suede Chukka Boots With Lace-Up Design - Casual Lightweight Ankle Boots For Everyday Wear
LightIntheBox.com
$54.99
Men's Beige Faux Suede Chukka Boots With Lace-Up Design - Casual Lightweight Ankle Boots For Everyday Wear
LightIntheBox.com
$160.00
Tommy Bahama Men's Olukai Papaku 'Ili Chukka Boots - Graphite - Size 10
Tommy Bahama
$160.00
Tommy Bahama Men's Olukai Papaku 'Ili Chukka Boots - Graphite - Size 10
Tommy Bahama
$23.99
$59.99
Sonoma Goods For Life® Hommer Freer Men's Comfort Chukka Boots, Size: 9.5, Black
Kohl's
60% off
$23.99
$59.99
Sonoma Goods For Life® Hommer Freer Men's Comfort Chukka Boots, Size: 9.5, Black
Kohl's
$265.00
Gordon Rush Men's Austin Dress Three-Eye Chukka Boots - Espresso - Size 9.5
Macy's
Free shipping
$265.00
Gordon Rush Men's Austin Dress Three-Eye Chukka Boots - Espresso - Size 9.5
Macy's
$269.99
Men's Weekender Chukka In Chocolate Muleskinner Leather 3315 | Red Wing Heritage
Red Wing
$269.99
Men's Weekender Chukka In Chocolate Muleskinner Leather 3315 | Red Wing Heritage
Red Wing

Shop men's chukka boots

Sponsored
About our ads
$29.99
$100.00
St. John's Bay Mens Acton Flat Heel Chukka Boots | Brown | Regular 10 1/2 | Boots Chukka Boots | Memory Foam | Holiday Gifts
JCPenney
35
70% off
$29.99
$100.00
St. John's Bay Mens Acton Flat Heel Chukka Boots | Brown | Regular 10 1/2 | Boots Chukka Boots | Memory Foam | Holiday Gifts
JCPenney
35
$90.00
Cole Haan Chester Chukka - Brown / Men'scasual - Size 11
Shoes for Crews
$90.00
Cole Haan Chester Chukka - Brown / Men'scasual - Size 11
Shoes for Crews
$110.00
Skechers Men's Hands Free Slip-Ins John Deere Waterproof: Respected - Tanzier Boots | Size 14.0 | Olive/Brown | Leather/Synthetic
Skechers USA
2
$110.00
Skechers Men's Hands Free Slip-Ins John Deere Waterproof: Respected - Tanzier Boots | Size 14.0 | Olive/Brown | Leather/Synthetic
Skechers USA
2
$105.00
Skechers Men's Relaxed Fit: Respected - Boswell Boots | Size 8.5 | Brown | Leather/Synthetic
Skechers USA
877
$105.00
Skechers Men's Relaxed Fit: Respected - Boswell Boots | Size 8.5 | Brown | Leather/Synthetic
Skechers USA
877
$35.00
MOZO Speakeasy Chukka 4SG - Brown / Men's4-Season Grip - Size 11
Shoes for Crews
$35.00
MOZO Speakeasy Chukka 4SG - Brown / Men's4-Season Grip - Size 11
Shoes for Crews
$26.99
$90.00
St. John's Bay Mens Mills Flat Heel Chukka Boots | Black | Regular 8 1/2 | Boots Chukka Boots | Memory Foam
JCPenney
70% off
$26.99
$90.00
St. John's Bay Mens Mills Flat Heel Chukka Boots | Black | Regular 8 1/2 | Boots Chukka Boots | Memory Foam
JCPenney
$110.00
Skechers Men's Hands Free Slip-Ins Relaxed Fit: Pollard - Waylon Boots | Size 11.0 | Red/Brown | Leather/Synthetic/Metal
Skechers USA
2
$110.00
Skechers Men's Hands Free Slip-Ins Relaxed Fit: Pollard - Waylon Boots | Size 11.0 | Red/Brown | Leather/Synthetic/Metal
Skechers USA
2
$129.99
Redhead Series 61 Chukka Boots For Men - Russet - 11m
Cabela's
$129.99
Redhead Series 61 Chukka Boots For Men - Russet - 11m
Cabela's
$1,320.00
Gucci Men's Sylke Suede Bit Lug-Sole Chukka Boots, Nocciola, Men's, 11, Boots Chukka & Desert Boots
Neiman Marcus
1
Free shipping
$1,320.00
Gucci Men's Sylke Suede Bit Lug-Sole Chukka Boots, Nocciola, Men's, 11, Boots Chukka & Desert Boots
Neiman Marcus
1
$140.00
Men's Heritage Suede Chukka Boot In Whiskey, Size 10, Suede Leather By Quince
Quince
Free shipping
$140.00
Men's Heritage Suede Chukka Boot In Whiskey, Size 10, Suede Leather By Quince
Quince
Free shipping
$122.98
MOZO Speakeasy Chukka 4SG - Black / Men's4-Season Grip - Size 9.5
Shoes for Crews
$122.98
MOZO Speakeasy Chukka 4SG - Black / Men's4-Season Grip - Size 9.5
Shoes for Crews
$149.99
Timberland Britton Chukka Boot | Men's | Dark Brown | Size 9 | Boots | Chukka
DSW
Free shipping
$149.99
Timberland Britton Chukka Boot | Men's | Dark Brown | Size 9 | Boots | Chukka
DSW
Free shipping
$140.00
Men's Heritage Suede Chukka Boot In Charcoal, Size 10.5, Suede Leather By Quince
Quince
Free shipping
$140.00
Men's Heritage Suede Chukka Boot In Charcoal, Size 10.5, Suede Leather By Quince
Quince
Free shipping
$319.00
Suede Chukka Boots - Tobacco Brown Size 10 By Charles Tyrwhitt
Charles Tyrwhitt
$319.00
Suede Chukka Boots - Tobacco Brown Size 10 By Charles Tyrwhitt
Charles Tyrwhitt
$890.00
Santoni Men's Gregory Suede Chukka Boots, Brown, Men's, 9, Boots Chukka & Desert Boots
Neiman Marcus
Free shipping
$890.00
Santoni Men's Gregory Suede Chukka Boots, Brown, Men's, 9, Boots Chukka & Desert Boots
Neiman Marcus
Free shipping
$134.99
Timberland Redwood Falls Chukka Boot | Men's | Dark Brown | Size 10 | Boots | Lug
DSW
Free shipping
$134.99
Timberland Redwood Falls Chukka Boot | Men's | Dark Brown | Size 10 | Boots | Lug
DSW
Free shipping
$1,320.00
Gucci Men's Sylke Suede Bit Lug-Sole Chukka Boots, Oatmeal, Men's, 10D, Boots Chukka & Desert Boots
Neiman Marcus
1
Free shipping
$1,320.00
Gucci Men's Sylke Suede Bit Lug-Sole Chukka Boots, Oatmeal, Men's, 10D, Boots Chukka & Desert Boots
Neiman Marcus
1
$99.00
Clarks - Mens - Walpath Chukka Waterproof Leather - 8.5 - Black
ClarksUSA.com
$99.00
Clarks - Mens - Walpath Chukka Waterproof Leather - 8.5 - Black
ClarksUSA.com