Best Chukka Boots for Men of 2025

"I've ordered these boots twice over six years. I really like their look, and the leather holds up well with care. I chose half a size down, expecting the leather to stretch, and they fit alright. However, the inside feels a bit hard, so I recommend using an insole for long periods of wear. The soles wore down after a few years, which is why I replaced them, but the leather held up nicely. They get lots of compliments and work well with both casual and dressy outfits."

"The quality of the leather is excellent for the price. These boots are well-constructed and comfortable. They appear darker brown initially but likely lighten with wear. I found they run at least half a size large, so I suggest sizing down. I love the dark brown color and am considering getting another pair in a lighter shade or gray suede. These boots are very versatile!"

"I absolutely love these shoes! They're strong, look great, and are perfect for rainy days. I find them very reliable and comfortable."

"I used these boots for a 9-mile hike along the coast and they handled the harsh terrain remarkably well. They fit perfectly to my measurements, and despite being overweight, they were surprisingly comfortable. I had no blisters, and my feet were unscathed. The durability was impressive, and the grip made trekking enjoyable. However, they aren't very waterproof, so I wouldn't recommend them for marshy areas."

"I found these boots for $18, and I can't believe how happy I am with them! They look fantastic and are quite comfortable. The grippy outsole is a plus, and they didn't require any break-in period. The ankle zipper is convenient for quick wear. I’ve received many compliments on them, and people are shocked by the price!"

"I bought these boots for my boyfriend, and he absolutely loves them! He says they are so comfortable and fit him perfectly. He was pleasantly surprised by their durability, especially considering the price."

"I was really hoping for better shoes, but for $30, I can't expect them to be great! They are fairly comfortable and true to size. However, the loop on the back tore off during my first attempt to put them on, and they squeak quite a bit. Overall, they are okay for the price, but I wouldn't expect them to hold up."

"I got the Bruno Marc boots and they are fantastic! I wear them for work, knowing they might not last long, but they are comfortable all day. I get compliments daily, although some say they are too dressy for work. I don't mind; I love how they feel!"

"I recently bought these boots in black and I'm thrilled! They blend comfort, style, and affordability perfectly. I have bad feet, so comfort is crucial for me. The interior is soft and cushions my feet, allowing me to wear them for long periods without discomfort. I’ve received a lot of compliments, but I did notice the laces started to fray after a week."

“I love these boots! They are perfect for dressing up or down. My husband really enjoys how comfortable and durable they are, plus they are lightweight!”

“I purchased these for riding my motorcycle, and they have a firm sole that prevents slipping. Living in Florida, I appreciate that they don't make my feet too hot, and I really like wearing them to the beach!”

“As a big Timberland fan, I was excited to try these. They add a great element of style while still providing the comfort I expect from Timberland. Definitely a good buy!”

"I was pleasantly surprised by how stylish and comfortable these boots are. They fit true to size and I believe they could easily be worn by anyone."

"For the price, these boots are a great deal. However, I did notice they scuff easily, which is a small downside."

"I had no idea boots could be this lightweight! They fit snugly and are incredibly comfortable, especially around the ankles."

"I chose the natural suede because I believe it offers the best look for chukkas. They are stylish yet not overly formal, making them suitable for anything from jeans to chinos. The suede feels thin but looks great and seems durable. The fit was just right for my usual size, and they are comfortable without a liner. I treated them with suede sealer, and they absorbed it perfectly. They complement my brown leather Clarks well, and I consider them my summer chukkas here in Florida. A fantastic value for the price!"

"I received my shoes yesterday and wore them around the house. I typically wear a 10.5, but I ordered a 10.5 for these as well. Initially, they felt a little snug in the toe box, likely because it’s a bit stiff. However, after wearing them all day at work, they feel just right! The quality is impressive: the leather is nice, the soles grip well, and the waxed laces are the perfect length and stay tied. I don’t think I’ll switch back to regular oxfords since I prefer the ankle boots for comfort. Finding a matching belt was a bit tricky, but I eventually found one that fits well with the shoe color. I can’t believe these are under $40; they look like they cost much more!"

"When you’re on your feet all day, comfort is key. These are my third pair, and I’ve already ordered a fourth! My first two pairs have lasted two years and are still incredibly comfortable. I highly recommend giving them a try; you won’t regret it!"

"I’ve found that the Ariat Men's Spitfire Boots are my go-to footwear. They’re incredibly comfortable right from the start, and the cushioned insole supports me for all-day wear. I appreciate the versatile design, as they go well with both casual and slightly dressier outfits. Plus, they’re durable enough for my daily errands or outings with friends. I highly recommend these boots for anyone seeking a reliable pair!"

"I bought the black leather version about a month ago, and they look great! They sit nicely between dressy and casual. Being someone with neuropathic foot pain, I found them to be really comfortable right from the minute I put them on. I’m curious to see how they hold up over time!"

"After trying multiple brands, including Twisted X, I can confidently say these Ariat boots are the most comfortable I’ve found. The fit was perfect in my usual size, and I absolutely love them!"

"I bought these Clarks Men's Shacre Ankle Boots in black suede, size 11, and I absolutely love them! Comfort is top-notch with excellent cushioning for all-day wear. The style is sleek and versatile, perfect for both casual and semi-formal outfits. The build quality is impressive, with a durable rubber outsole and smooth textile linings. Just keep in mind that they run a bit large, so ordering a half size down may be wise. Plus, the suede needs regular care, especially in wet conditions. Overall, I highly recommend these boots!"

"My son is a huge fan of these shoes! They offer great value for money and are super comfortable. The fit was a bit snug at first, but it’s perfect now. I’m really pleased with this purchase!"

"I've been a fan of Wallabees since the 70s, and I still think everyone should own a pair. They combine quality and comfort seamlessly. These shoes are well-made, featuring genuine leather and a beeswax coating. I constantly get compliments from others, which is a rarity among guys. The ankle support is fantastic, and they fit perfectly. I just wish I had bought them sooner!"

"I find these boots to be extremely comfortable and they fit perfectly, with no pinch points. The waterproof feature will definitely come in handy for snow and rain."

"My husband is a big fan of these boots. We had to repurchase after our dog chewed through one pair, but they're totally worth it for their comfort and stylish look."

"I bought these for my son for a mission trip because they look dressy yet comfortable. He loved them so much that my husband decided to keep the second pair I ordered!"

"I've been wearing these boots for nearly two years and they are still holding up strong. I use them for both rough terrain and board meetings. It's the first boot that looks decent and hasn't split at the bend or leather. I highly recommend them!"

"I haven't loved a pair of boots like these in ages. They felt amazing even after a whole weekend on my feet. I suggest using mink oil to maintain the leather. I’d even consider buying a second pair just to have a backup!"

"I bought my first pair over six years ago, and I can hardly count the days I haven't worn them! They've survived everything from long office hours to hunting in different weather. They look good with anything and never let me down. Seriously, you should buy a pair!"