The 10 Best Chukka Boots Money Can Buy

Allen Edmonds Higgins Mill Boot with Chromexcel Leather

Have you ever wished that you could get your hands on a pair of good chukka boots, the ankle high leather boots that many people think are the most comfortable footwear they have ever owned? It’s easy to see why you might have daydreams about owning a pair of boots like this. Some people have the misconception that these boots are always more expensive than the overwhelming majority of the public is willing to pay. That simply isn’t true. Granted, some are more expensive than others but a lot of them are reasonably priced. If you’re curious, check out the list below. It features the top 10 chukka boots that money can buy.

Beckett Simonon Laval Chukka Boots in Brown

10. Beckett Simonon Laval Chukka Boots in Brown ($239)

If you think $239 is a lot of money to pay for a pair of boots, consider this fact. These boots have traditionally sold for as much as $400. It’s easy to understand why. They’re made from full-grain leather and they’re upscale enough to be worn with a suit, yet durable and comfortable enough to be worn for a day spent walking around. This particular variety can be purchased in five different colors and in sizes ranging from 7 to 14.

Allen Edmonds Higgins Mill Boot with Chromexcel Leather

9. Allen Edmonds Higgins Mill Boot with Chromexcel Leather ($311.50)

This particular boot is a high-quality workman-style boot made from imported materials and manufactured in the United States. It’s available in brown and in sizes 6.5 to 15. There are even four different widths the boot can be purchased in, something that is virtually unheard of. For anyone who is suffering from sticker shock from the $300 price, it’s important to know that most customers can pay in installments, with four consecutive payments of $78.88.

Veldskoen Men’s Leather Hand-Crafted Chukka Boot

8. Veldskoen Men’s Leather Hand-Crafted Chukka Boot ($179)

This is another boot that could easily fit in several different roles. It looks good enough to be worn with business casual attire, but it also works equally well for working on a ranch or a farm. By the same token, a lot of people use these types of boots to go hiking. They’re comfortable, so they’re excellent for long walks, especially when those walks exist over uneven terrain. It’s brown in color and is currently available in sizes 4 to 15.

Peter Millar Excursionist Men’s Chukka Boots

7. Peter Millar Excursionist Men’s Chukka Boots ($298)

These shoes have a lot going for them. For starters, they’re designed to look like a high-end suede shoe and they’re available in a number of different colors. For example, the colors available include espresso, avio blue, terrace (gray), vermouth (red) and dark amber. By the same token, you can get them in sizes ranging from 8 to 13. The shoes ship the next business day, so you won’t have to wait long to get a pair of your own.

Freebird Ace

6. Freebird ACE ($245)

The thing that is genuinely surprising here is that the boots are designed to look like they have been worn and weathered for a number of years. It gives them character. From a practical perspective, it also makes leather boots more comfortable because all of that weathering has a tendency to make them feel like they’re broken in the moment you take them out of the box. If you want to get your hands on a pair of these, you’ll have to act quickly. Currently, they only have them available in stone and the only size that they have in stock is 13.

Apex Men’s Hudson Chukka Boot in Brown

5. Apex Men’s Hudson Chukka Boot in Brown ($162.95)

There are a lot of things that make these particular boots special. Perhaps the most important thing is that they were designed specifically to help with certain conditions, including things like heel pain, hammer toe and bunions. By the same token, they can also help alleviate some of the pain caused by plantar fasciitis and even more serious diseases such as diabetes, neuropathy, and even some cancers. The shoe itself is brown in color and is currently available in sizes 4 to 14.

Beckett Simonon Nolan Brogue Boots in Tan

4. Beckett Simonon Nolan Brogue Boots in Tan ($239)

These are sturdy boots that can be worn on a variety of different occasions. They are tan in color with broguing on both the toes and heels. They come in sizes ranging from 7 all the way to 14. As is the case with some of the other chukka boots made by this particular company, the asking price of $239 is a real bargain. Typically, they go for $400.

Daytripper Chukka Boots Waxed Brown Nisolo

3. Daytripper Chukka Boots Waxed Brown Nisolo ($160)

Available in sizes 8 to 10, these suede boots are made from reclaimed materials and are easy to clean up, even when they’ve really been put through the ringer. They’re also comfortable. This means they can be worn for special events, in the office or when spending virtually the entire day on your feet.

Kramerr Tan Leather Boots by Steve Madden

2. Kramerr Tan Leather Boots by Steve Madden ($159.95)

Perhaps the greatest thing about these boots is that they look like they’ve been broken in just enough to be comfortable, yet not so much that they look like it’s time to replace them. Better still, you can purchase them without paying anything upfront, as the company allows you to wait until two weeks after your purchase date to make your first payment. This gives you plenty of time to try them out for yourself.

1. Frye Murray Chukka Men’s Lace-Up Boots ($297.90)

These boots fit true to size and they’re supple enough to conform to the shape of your foot quickly and easily. They also look great, so you can even wear them to work in most cases. They’re currently available in select sizes, so you may want to snatch a pair before your size is out of stock.

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