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Leather Chukkas

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55 Items

Men's Lookout Leather Chukka Boots

Men's Lookout Leather Chukka Boots

Ariat Men's Lookout Leather Chukka Boots

Only size 11 available

Men's Harrison Leather Chukka Boots

Men's Harrison Leather Chukka Boots

Born Men's Harrison Leather Chukka Boots

Internet Exclusive

Men's Illiad Leather Chukka Boots

Men's Illiad Leather Chukka Boots

Bed Stu Men's Illiad Leather Chukka Boots

Men's Upton Leather Chukka Boots

Men's Upton Leather Chukka Boots

Johnston & Murphy Men's Upton Leather Chukka Boots

Permanently Reduced

Men's Paul Leather Chukka Boots

Men's Paul Leather Chukka Boots

Frye Men's Paul Leather Chukka Boots

Internet Exclusive

Men's Morse Leather Chukka Boots

Men's Morse Leather Chukka Boots

Cole Haan Men's Morse Leather Chukka Boots

Men's Calder Leather Chukka Lace Up Boots

Men's Calder Leather Chukka Lace Up Boots

Johnston & Murphy Men's Calder Leather Chukka Lace Up Boots

Men's Driving Leather Moc Toe Chukka Boots

Men's Driving Leather Moc Toe Chukka Boots

Twisted X Men's Driving Leather Moc Toe Chukka Boots

Men's Driving Leather Moccasin Chukka Boots

Men's Driving Leather Moccasin Chukka Boots

Twisted X Men's Driving Leather Moccasin Chukka Boots

Men's Chukka Driving Moccasins

Men's Chukka Driving Moccasins

Twisted X Men's Chukka Driving Moccasins

Internet Exclusive

Women's Embroidered Leather Driving Moc Toe Chukka Boots

Women's Embroidered Leather Driving Moc Toe Chukka Boots

Twisted X Women's Embroidered Leather Driving Moc Toe Chukka Boots

Men's Astor Leather Chukka Boots

Men's Astor Leather Chukka Boots

Frye Men's Astor Leather Chukka Boots

Men's Larkin Leather Plain Toe Chukka Boots

Men's Larkin Leather Plain Toe Chukka Boots

Johnston & Murphy Men's Larkin Leather Plain Toe Chukka Boots

Permanently Reduced

Men's Braxton Oiled Leather Chukka Boots

Men's Braxton Oiled Leather Chukka Boots

Johnston & Murphy Men's Braxton Oiled Leather Chukka Boots

Permanently Reduced

Men's Vista Chukka Boots

Men's Vista Chukka Boots

To Boot New York Men's Vista Chukka Boots

Permanently Reduced

Women's Printed Leather Driving Moc Toe Chukka Boots

Women's Printed Leather Driving Moc Toe Chukka Boots

Twisted X Women's Printed Leather Driving Moc Toe Chukka Boots

Women's Original Leather Driving Moc Toe Chukka Boots

Women's Original Leather Driving Moc Toe Chukka Boots

Twisted X Women's Original Leather Driving Moc Toe Chukka Boots

Men's Driving Woven Leather Moccasin Chukka Boots

Men's Driving Woven Leather Moccasin Chukka Boots

Twisted X Men's Driving Woven Leather Moccasin Chukka Boots

Men's Driving Moccasin Chukka Boots

Men's Driving Moccasin Chukka Boots

Twisted X Men's Driving Moccasin Chukka Boots

Internet Exclusive

Men's Allagash Handsewn Leather Chukka Boots

Men's Allagash Handsewn Leather Chukka Boots

L.L.Bean Men's Allagash Handsewn Leather Chukka Boots

Permanently Reduced

Men's Earl 04 Leather Lace Up Chukka Boots

Men's Earl 04 Leather Lace Up Chukka Boots

Josef Seibel Men's Earl 04 Leather Lace Up Chukka Boots

Men's Chukka Hiker Waterproof Boots

Men's Chukka Hiker Waterproof Boots

Twisted X Men's Chukka Hiker Waterproof Boots

Men's Madson II Waterproof Leather Chukka Boots

Men's Madson II Waterproof Leather Chukka Boots

Sorel Men's Madson II Waterproof Leather Chukka Boots

Internet Exclusive

Men's Chukka Driving Mocs

Men's Chukka Driving Mocs

Twisted X Men's Chukka Driving Mocs

Men's Chukka Driving Mocs

Men's Chukka Driving Mocs

Twisted X Men's Chukka Driving Mocs

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Men's Chukka Driving Mocs

Men's Chukka Driving Mocs

Twisted X Men's Chukka Driving Mocs

Men's Chukka Driving Mocs

Men's Chukka Driving Mocs

Twisted X Men's Chukka Driving Mocs

Internet Exclusive

Men's Slip-On Chukka Leather Driving Moccasin Boots

Men's Slip-On Chukka Leather Driving Moccasin Boots

Twisted X Men's Slip-On Chukka Leather Driving Moccasin Boots

Internet Exclusive

Men's Tabriz Lace Up Leather Chukka Boots

Men's Tabriz Lace Up Leather Chukka Boots

Steve Madden Men's Tabriz Lace Up Leather Chukka Boots

Permanently Reduced

Boys' Calder Leather Lace Up Chukka Boots (Youth)

Boys' Calder Leather Lace Up Chukka Boots (Youth)

Johnston & Murphy Boys' Calder Leather Lace Up Chukka Boots (Youth)

Women's Embroidered Moc Toe Driving Chukka Booties

Women's Embroidered Moc Toe Driving Chukka Booties

Twisted X Women's Embroidered Moc Toe Driving Chukka Booties

Internet Exclusive

Men's Calder 175th Anniversary Leather Chukka Boots

Men's Calder 175th Anniversary Leather Chukka Boots

Johnston & Murphy Men's Calder 175th Anniversary Leather Chukka Boots

Permanently Reduced

Sculpted C Leopard Print Calf Hair Chukka Oxfords

Sculpted C Leopard Print Calf Hair Chukka Oxfords

COACH Sculpted C Leopard Print Calf Hair Chukka Oxfords

Internet Exclusive

Only size 8 available

Men's Redwood Falls Waterproof Leather Chukka Boots

Men's Redwood Falls Waterproof Leather Chukka Boots

Timberland Men's Redwood Falls Waterproof Leather Chukka Boots

Permanently Reduced

Internet Exclusive

Women's Sunflower Leather Driving Moc Toe Chukka Boots

Women's Sunflower Leather Driving Moc Toe Chukka Boots

Twisted X Women's Sunflower Leather Driving Moc Toe Chukka Boots

Analia Distressed Suede Ankle Chukka Booties

Analia Distressed Suede Ankle Chukka Booties

Born Analia Distressed Suede Ankle Chukka Booties

Men's Driving Woven Moccasin Chukka Boots

Men's Driving Woven Moccasin Chukka Boots

Twisted X Men's Driving Woven Moccasin Chukka Boots

Boys' McGuffey Leather Lace Up Chukka Boots (Youth)

Boys' McGuffey Leather Lace Up Chukka Boots (Youth)

Johnston & Murphy Boys' McGuffey Leather Lace Up Chukka Boots (Youth)

Permanently Reduced

Women's Tooled Moc Toe Driving Chukka Booties

Women's Tooled Moc Toe Driving Chukka Booties

Twisted X Women's Tooled Moc Toe Driving Chukka Booties

Only size 7.5, 6.5 available

Men's Split Rock Leather Moc Toe Chukka Boots

Men's Split Rock Leather Moc Toe Chukka Boots

Ariat Men's Split Rock Leather Moc Toe Chukka Boots

Men's Ayden Moc Toe Waterproof Leather Lace Up Chukka Boots

Men's Ayden Moc Toe Waterproof Leather Lace Up Chukka Boots

Flag LTD.Men's Ayden Moc Toe Waterproof Leather Lace Up Chukka Boots

Permanently Reduced

Dillard´s Exclusive

Men's XC+Parker Waterproof Leather Chukka Boots

Men's XC+Parker Waterproof Leather Chukka Boots

Johnston & Murphy Men's XC+Parker Waterproof Leather Chukka Boots

Permanently Reduced

Women's Inquire Chukka Waterproof Leather Hiking Boots

Women's Inquire Chukka Waterproof Leather Hiking Boots

Danner Women's Inquire Chukka Waterproof Leather Hiking Boots

Men's Eco Bay Nubuck Chukka Boots

Men's Eco Bay Nubuck Chukka Boots

L.L.Bean Men's Eco Bay Nubuck Chukka Boots

Permanently Reduced

Men's Work Steel Toe Leather Chukka Driving Moccasins

Men's Work Steel Toe Leather Chukka Driving Moccasins

Twisted X Men's Work Steel Toe Leather Chukka Driving Moccasins

Women's Stone Street Mid Lace Up Waterproof Chukka Booties

Women's Stone Street Mid Lace Up Waterproof Chukka Booties

Timberland Women's Stone Street Mid Lace Up Waterproof Chukka Booties

Internet Exclusive

Men's Chamberlin Water Resistant Nubuck Chukka Boots

Men's Chamberlin Water Resistant Nubuck Chukka Boots

Cole Haan Men's Chamberlin Water Resistant Nubuck Chukka Boots

Internet Exclusive

Men's Waterproof Driving Moccasins Chukka Boots

Men's Waterproof Driving Moccasins Chukka Boots

Twisted X Men's Waterproof Driving Moccasins Chukka Boots

Internet Exclusive

Boys' Calder Leather Hook-and-Loop Chukka Boots (Toddler)

Boys' Calder Leather Hook-and-Loop Chukka Boots (Toddler)

Johnston & Murphy Boys' Calder Leather Hook-and-Loop Chukka Boots (Toddler)

Men's Driving CellStretch Leather Moc Toe Chukka Boots

Men's Driving CellStretch Leather Moc Toe Chukka Boots

Twisted X Men's Driving CellStretch Leather Moc Toe Chukka Boots

Boys' Calder Leather Hook-and-Loop Chukka Boots (Infant)

Boys' Calder Leather Hook-and-Loop Chukka Boots (Infant)

Johnston & Murphy Boys' Calder Leather Hook-and-Loop Chukka Boots (Infant)

Boys' McGuffey Leather Hook-and-Loop Chukka Boots (Infant)

Boys' McGuffey Leather Hook-and-Loop Chukka Boots (Infant)

Johnston & Murphy Boys' McGuffey Leather Hook-and-Loop Chukka Boots (Infant)

Permanently Reduced

Boys' McGuffey Leather Alternative Closure Chukka Boots (Toddler)

Boys' McGuffey Leather Alternative Closure Chukka Boots (Toddler)

Johnston & Murphy Boys' McGuffey Leather Alternative Closure Chukka Boots (Toddler)

Permanently Reduced

Women's Tooled Turquoise Stud Driving Moc Toe Chukka Boots

Women's Tooled Turquoise Stud Driving Moc Toe Chukka Boots

Twisted X Women's Tooled Turquoise Stud Driving Moc Toe Chukka Boots

Men's Chukka Driving CellStretch Mocs

Men's Chukka Driving CellStretch Mocs

Twisted X Men's Chukka Driving CellStretch Mocs

Internet Exclusive

55 Items

About Leather Chukkas

Discover the timeless appeal of leather chukkas, a versatile footwear choice that combines style and comfort. These ankle-high boots are crafted from premium leather, providing durability and a sophisticated look suitable for various occasions. With their classic silhouette and modern designs, leather chukkas can effortlessly elevate both casual and semi-formal outfits.

Designed for all-day wear, leather chukkas feature cushioned insoles and sturdy outsoles for enhanced comfort and support. Available in a range of colors and finishes, these boots offer a perfect blend of functionality and fashion, making them a staple in any wardrobe.

What are leather chukkas?

Leather chukkas are ankle-length boots typically made from high-quality leather. They are characterized by their simple design, often featuring two or three eyelets for laces, making them easy to wear and style.

Are leather chukkas suitable for formal occasions?

Yes, leather chukkas can be suitable for formal occasions, especially when paired with tailored trousers or chinos. Their sleek design and premium materials add a touch of sophistication to smart-casual and business-casual outfits.

How do I style leather chukkas?

Leather chukkas can be styled in various ways, making them versatile for different looks. They pair well with jeans, chinos, and even dress pants, and can be complemented with casual shirts, blazers, or sweaters for a polished appearance.

What makes leather chukkas comfortable?

Leather chukkas are designed with comfort in mind, featuring cushioned insoles and flexible outsoles that provide support during extended wear. The natural breathability of leather also helps keep feet comfortable throughout the day.

Can leather chukkas be worn in different seasons?

Yes, leather chukkas are versatile enough to be worn in various seasons. They can be paired with lighter fabrics in warmer months and layered with socks or heavier clothing during colder seasons, making them a year-round footwear option.

How do leather chukkas differ from other boot styles?

Leather chukkas differ from other boot styles primarily in their height and design. They are shorter than traditional boots, typically reaching just above the ankle, and feature a more casual aesthetic compared to dress boots or work boots.

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