Best Wingtip Chukka Boots for Men of 2025

William Weston Avatar
William Weston
Last Updated: Jan 6, 2025

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The Wingtip Chukka Boots are a classic and sophisticated footwear option for men. These boots feature a timeless wingtip design, combining elegant brogue detailing with the casual appeal of chukka boots. Crafted with high-quality leather, they offer durability and comfort. The lace-up closure ensures a secure fit, while the rubber sole provides traction and support. Suitable for both formal and casual occasions, these Wingtip Chukka Boots are a versatile addition to any man's wardrobe.

At a Glance: Our Top Picks

Nunn Bush Odell 2.0 Chukka Boot Cover #TOP 1
Nunn Bush Odell 2.0 Chukka Boot
ftb score rating icon 9.8
Nunn Bush Odell Chukka Boot Cover #TOP 2
Nunn Bush Odell Chukka Boot
ftb score rating icon 9.7
Nunn Bush Men's Odell Wingtip Chukka Boot Cover #TOP 3
Nunn Bush Men's Odell Wingtip Chukka Boot
ftb score rating icon 9.5

Top 10 Wingtip Chukka Boots for Men

#TOP 1

Nunn Bush Odell 2.0 Chukka Boot

85089-239
13 X-Wide
Nunn Bush Odell 2.0 Chukka Boot Cover
Nunn Bush Men's Odell 2.0 Wingtip Dress Casual Chukka Leather Boot, Tan, 13 X-Wide

The Nunn Bush Chukka Boot combines style and comfort for the modern man. With its updated design, you'll enjoy enhanced comfort from the molded dual comfort EVA footbed, which provides excellent arch support and shock absorption. The premium leather uppers ensure both durability and a polished look, making these boots perfect for dressing up or down with jeans or chinos. Plus, the availability of various widths guarantees a snug fit tailored to your feet, allowing you to wear them all day without discomfort.

What We Like
Enhanced comfort technology
Stylish premium leather design
Available in multiple widths
Lightweight and shock-absorbent sole
#TOP 2

Nunn Bush Odell Chukka Boot

84776-007
Brown Crazy Horse
Nunn Bush Odell Chukka Boot Cover
Nunn Bush Men's Odell Wingtip Chukka Boot with KORE Comfort Technology, Brown Crazy Horse, 10 Medium

The Nunn Bush Chukka Boot is designed for both style and comfort. Made from premium leather, it enhances your wardrobe while providing versatile options for casual outings. You’ll appreciate the full-length Memory Foam footbed, which offers exceptional cushioning and shock absorption, making it perfect for all-day wear. The boot also ensures a great fit with options in various widths, so your feet can feel pampered and supported. Additionally, the KORE dual-density outsole is lightweight and engineered for walking, giving you athletic comfort with every step.

What We Like
Comfortable Memory Foam footbed
Versatile style for outfits
Multiple width options
Lightweight and shock-absorbing outsole
#TOP 3

Nunn Bush Men's Odell Wingtip Chukka Boot

84776-007
Black
Nunn Bush Men's Odell Wingtip Chukka Boot Cover
Nunn Bush Men's Odell Wingtip Chukka Boot with KORE Comfort Technology , Black , 10 Medium

The Nunn Bush Men's Odell Wingtip Chukka Boot is made with premium leather uppers, memory foam footbed, and KORE dual density outsole for superior shock absorption and cushioning. It is available in medium, wide, and extra wide widths, providing the perfect fit. The versatile style makes it suitable for jeans and chinos, perfect for everyday wear. Nunn Bush is a premier footwear brand since 1912, providing the best value and style in fine men's footwear.

What We Like
Premium leather uppers
Memory foam footbed for superior cushioning
Available in medium, wide, and extra wide widths for the perfect fit
Versatile style suitable for everyday wear
Provided by a premier footwear brand since 1912
#TOP 4

Florsheim Renegade Wingtip Boot

15202-001
Black
Florsheim Renegade Wingtip Boot Cover
Florsheim Renegade Wingtip Lace Up Boot Mens Boot 85 DM US Black

The Florsheim Wingtip Boot is a stylish casual option for men, crafted with a smooth leather upper that not only looks great but also offers durability. The convenient zip closure allows for easy on and off, making it perfect for those busy mornings. Inside, you'll find breathable textile linings that help keep your feet comfortable throughout the day. Plus, the fully-cushioned, removable footbed features high-rebound foam and molded EVA, providing excellent support and comfort for all-day wear. This combination of features makes the Florsheim Wingtip Boot a practical choice for both work and leisure.

What We Like
Durable leather upper
Easy zip closure
Breathable linings
Cushioned footbed
#TOP 5

Nunn Bush Odell Wingtip Chukka Boot

84776-007
Black
10.5
Nunn Bush Odell Wingtip Chukka Boot Cover
Nunn Bush Men's Odell Wingtip Chukka Boot with KORE ComfortTechnology, Black, 10.5 Medium US

Get the perfect combination of style and comfort with the Nunn Bush Odell Wingtip Chukka Boot. Made with premium leather uppers, this classic boot adds a touch of sophistication to any outfit. The full-length Memory Foam footbed and molded heel cup provide all-day shock absorption and cushioning, ensuring superior comfort. With a versatile design, these boots can easily be paired with jeans or chinos. The KORE dual-density outsole is biomechanically designed for walking, providing athletic-inspired comfort and shock absorption. Pamper your feet with this amazing walking shoe that offers a perfect fit in medium, wide, and extra-wide widths. Nunn Bush has been a trusted footwear brand since 1912, offering the best value and style in men's footwear.

What We Like
Stylish and versatile
All-day comfort with Memory Foam footbed
Perfect fit in various widths
#TOP 6

Crevo Boardwalk Wing Tip Boot

Boardwalk
Black Leather
Crevo Boardwalk Wing Tip Boot Cover
Crevo Men's Boardwalk Wing Tip Boot, Black Leather, 10 M US

The Crevo Wing Tip Boot is a stylish choice for any man looking to combine comfort and sophistication. With its classic wingtip design and decorative detailing, this boot adds a refined touch to your outfit. You’ll appreciate the memory foam heel cup, which provides cushioning and support, making long wear a breeze. The boot's flexible non-slip EVA outsole ensures stability and grip, perfect for various surfaces. Whether at work or out on the town, these boots keep you looking sharp and feeling comfortable.

What We Like
Stylish wingtip design
Comfortable memory foam
Non-slip outsole
Flexible fit
#TOP 7

Nunn Bush Odell Chukka Boot

84776
Brown Crazy Horse
10 X-Wide
Nunn Bush Odell Chukka Boot Cover
Nunn Bush Men's Odell Wingtip Dress Casual Chukka Boot, Brown Crazy Horse, 10 X-Wide

The Nunn Bush Chukka Boot is designed with premium leather uppers, ensuring both style and comfort for your wardrobe. You can wear these versatile boots with jeans or chinos, making them a great choice for various occasions. The full-length memory foam footbed with a molded heel cup provides exceptional cushioning and shock absorption, perfect for all-day wear. Additionally, this boot is available in multiple widths, guaranteeing a comfortable fit for everyone. The KORE dual density outsole is lightweight and designed for walking, offering athletic-inspired comfort and support for your feet.

What We Like
Stylish leather design
All-day comfort
Multiple width options
Lightweight walking support
#TOP 8

Arkbird Captain Ankle Boots

Black (555)
Arkbird Captain Ankle Boots Cover
Arkbird Mens Dress Boots, Genuine Leather Captain Ankle Boots Lace-Up Wingtip

The Arkbird Dress Boots offer a stylish and comfortable option for your footwear collection. Made with high-quality leather, they provide durability and a sophisticated look that pairs well with jeans or chinos. The boots feature water-resistant laces that keep their shape and stay secure, ensuring your feet remain comfortable throughout the day. With a padded interior and specially designed synthetic soles, these boots deliver flexibility and impact resistance, making them perfect for various activities and environments. Plus, the KORE dual density outsole enhances shock absorption for a more comfortable walking experience.

What We Like
Premium leather construction
Water-resistant laces
Comfortable padded interior
Shock-absorbing outsole
#TOP 9

Nunn Bush Odell Chukka Boot

84776
Brown Crazy Horse
11 X-Wide
Nunn Bush Odell Chukka Boot Cover
Nunn Bush Men's Odell Wingtip Dress Casual Chukka Boot, Brown Crazy Horse, 11 X-Wide

The Nunn Bush Chukka Boot is crafted from high-quality leather, offering both style and comfort that can enhance your wardrobe. With a full-length memory foam footbed, it provides exceptional cushioning and shock absorption, perfect for long hours on your feet. This boot is designed for a great fit, available in various widths to ensure your feet feel pampered. The KORE dual-density outsole is specifically designed for walking, combining lightweight materials with athletic-inspired comfort that makes each step feel effortless.

What We Like
Premium leather construction
Memory foam cushioning
Available in multiple widths
Designed for walking comfort
#TOP 10

Nunn Bush Odell Wingtip Chukka Boot

84776
Tan Crazy Horse
10.5 X-Wide
Nunn Bush Odell Wingtip Chukka Boot Cover
Nunn Bush Men's Odell Wingtip Dress Casual Chukka Boot, Tan Crazy Horse, 10.5 X-Wide

The Nunn Bush Chukka Boot combines style and comfort seamlessly. Crafted with premium leather, it enhances your look, making it suitable for both jeans and chinos. With a full-length memory foam footbed, you can enjoy exceptional cushioning and shock absorption, perfect for all-day wear. The boot is designed for a perfect fit, available in various widths to accommodate your feet comfortably. Its KORE dual-density outsole offers lightweight support and athletic comfort, making each step easier. Whether you're at work or out on the town, this boot is a versatile addition to your wardrobe.

What We Like
Stylish premium leather
All-day comfort
Customizable fit options
Lightweight and supportive outsole
Buying Guide Image
Editor's Notes

During our wingtip chukka boots for men research, we found 48 wingtip chukka boots for men products and shortlisted 10 quality products. We collected and analyzed 8,908 customer reviews through our big data system to write the wingtip chukka boots for men list. We found that most customers choose wingtip chukka boots for men with an average price of $77.02.

The wingtip chukka boots for men are available for purchase. We have researched hundreds of brands and picked the top brands of wingtip chukka boots for men, including Nunn Bush, Florsheim, Crevo, Arkbird. The seller of top 1 product has received honest feedback from 385 consumers with an average rating of 4.7.

Written by
William Weston Avatar

William Weston was born in America and is currently a fashion industry designer. He's always been fascinated with the idea of taking something old and making it new again, so he decided to go into fashion design. William loves working on his designs and creating clothing that will make people look good while feeling comfortable at the same time.