Top 10 Men's Chukka Boots

The Most Versatile Shoe For Men To Wear This Fall

The Most Versatile Shoe For Men To Wear This Fall

If you only add one shoe style to your wardrobe this fall, let it be the classic, seasonless, and forever stylish chukka boot. Loved for their ultimate versatility, chukkas (or desert boots) can be worn with just about anything. Dark denim? Totally. Chinos? Absolutely. A suit? Go for it. They’ve got a dressy-but-not-too-dressy vibe, so they’re perfect for amping up jeans or toning down formal wear—the styling possibilities are pretty much endless. We also love that they’re both durable and comfortable, making them ideal for getting you through long days on your feet and fall’s worst weather. The question is: Is there anything this shoe can’t do? Today, we’re bringing you the scoop on the Top 10 chukka boots you can buy, from luxurious suede and vibrant shades to worn-in leather and neutral tones. This list is backed by our trusted algorithm factoring in top-sellers, user reviews, and fashion editor favorites—so you can fully trust these picks. Give your plain white sneakers the boot and elevate your ensemble with this work-to-weekend style! Opening image: @ClarksShoesUS

Did you like our 10 Best Men's Chukka Boots? Check out our 10 Best Men’s Sneakers for more top-ranked finds!

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October 29, 2019

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Top 10 Lists serve as unbiased shopping guides to the most trusted product recommendations on the internet. Products are scored and ranked using an algorithm backed by data consumers find most valuable when making a purchase. We are reader-supported and may earn a commission when you shop through our links.

The Rankings

UGG Dustin Chukka Boot
Rank & Style Approved


UGG Dustin Chukka Boot

BEST FOR: Say hello to your new fall shoe! The suede leather paired with the minimalistic design makes this pair great for everyday wear.

LOVED FOR: The lightweight sole, cushioned footbed, and high-quality material 

Florsheim Blaze Chukka Boot

BEST FOR: The top toe design give this boot an elegant touch that makes it ideal for the office. 

USERS SAID: "These boots were comfortable and stylish. The color of the leather is rich and the detailed stitching was top quality. They are versatile and can be dressed up or more casually and look amazing. Great buy!"

Cole Haan Original Grand Chukka Boot

WHY YOU NEED IT: The added arch support makes this one of the more comfortable pairs in this list. 

STYLE WITH: Pair with some black jeans and your favorite button-down for a stylish, casual workwear look. 

Johnston & Murphy Copeland Chukka Boots

USERS SAID: "This boot is very stylish and the most comfortable shoe I own. Felt like I was walking on pillows. A MUST HAVE........... I'm going to look at other colors right now!"

HELPFUL TIP: This boot runs small, size up for the perfect fit. 

Kenneth Cole Reaction Desert Sun Suede Chukkas

BEST FOR: If you happen to find Chukka boots uncomfortable due to the high shaft, then you'll love the low-cut profile of this pair. 

STYLE WITH: Good news, your fun, printed socks can officially be seen when you decide to wear these boots. 

Red Wing Heritage Weekender Chukka Boot

WHY YOU NEED IT: This American-crafted boot gets better with each wear. It's been carefully designed to withstand wear and tear while keeping comfort top of mind. 

ABOUT THE BRAND: Red Wing is a company known for making durable, comfortable footwear for hard-working people. Dating back to 1905, Red Wing first started in Red Wing, Minnesota. Their shoes and leather goods are still made in America today and sold in over 100 countries. 

Steve Madden Harken Chukka Boot

LOVED FOR: The slightly distressed, rich leather upper

STYLE WITH: These beauties are perfect for polishing up a pair of dark jeans!

Red Wing Classic Chukka Boot

BEST FOR: A chukka boot you can walk miles in while still looking stylish

USERS SAID: “Having bought many pairs of boots and dress shoes throughout the years, I am KICKING myself for not buying these earlier. Great fit, super comfortable and can be worn anywhere.”

Clarks Bushacre 2 Chukka Boot

WHY YOU NEED IT: With its high-quality leather and classic style, this boot is built to last—the marks and scuffs you gain along the way will only add to their cool factor.

LOVED FOR: The large selection of color options and leather styles means you'll find the exact boot to meet your needs. 

Clarks Stinson Hi Chukka Boot

WHY YOU NEED IT: This iconic shoe features clean and simple lines to withstand the test of time. 

USERS SAID: "I am a college professor, outdoors enthusiast, and dad of four small kids. I wear the beeswax wallabees every single day. I wear them to work, wear them out with the kids and basically doing everything. The waxed leather makes them fairly weather resistant, and the sole has held up far better than other leather shoes I have owned. I cannot recommend these shoes enough. Aside from the practicality, I constantly receive comments as to how much people like the looks of them. I plan on purchasing more of these in the future."

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