Best Chukka Boots for Men Under $50

Best Chukka Boots for Men Under $50

Posted by Issa on

We scour Amazon's large inventory of chukka shoes (affiliate link) to bring you the best-looking shoes priced below $50 that are totally worth it! To be honest, there's not much choices with this price range — maybe less than a hundred pair.

Note: This list is updated weekly to reflect changes in prices and availability.

1. Tommy Hilfiger Men's Monroe Chukka Boot

Price: $41.97

Tommy Hilfiger Men's Monroe Chukka Boot

A pair is made of 100% leather coupled with a synthetic sole. The rugged simplicity of its form is perfect for casual outfit. You can't go wrong with either grey or navy colors.

2. Steve Madden Men's Halloway Chukka Boot

Price: $29.89

Steve Madden Men's Halloway Chukka Boot

It comes in three different colors: tan, navy and camo. This boot is a great alternative to pricey business-casual chukka (except the camo, of course). It has the sleek form to pull it off. But if you're looking for an all-leather alternative by the same maker, check out Steve Madden Men's Harsen Chukka Boot (affiliate link).

3. Timberland Men's EK Hookset Camp Canvas Chukka

Price: $27.67

Timberland Men's EK Hookset Camp Canvas Chukka

Timberland has long been my favorite go-to shoemaker for affordable shoes. A pair of this canvas chukka offers the same sole-soul the company has been building. The rubber sole is made with shock-absorbing material and paired with a footbed engineered for all day comfort. And it comes with 5 different colors: Camo (pictured), Olive washed, Navy washed, Grey washed and Black.

4. Vans Unisex Chukka Slim Sweater Sneakers

Price: $40.99

Vans Unisex Chukka Slim Sweater Sneakers

I have to be honest. I never owned a pair of Vans before. I have always associated Vans with low-top sneakers. How naive. Imagine my surprise when I found this handsome shoes while browsing Amazon. The textile pattern on the upper that's made of cotton looks really good. But if you're looking for other colors, bad news. It only comes in this white/gray mix.