Chukka boots trace their roots back to the desert boots donned by British soldiers during the battles in Egypt and Libya in World War II. However, it wasn’t until 1949 when Clarks introduced their iconic Desert Boot with a crepe sole that this style truly gained commercial prominence. Over time, it became a fashion staple, particularly in the UK, where it played a significant role in the mod culture of the 1960s.

1. Loro Piana, Open Wintery Walk
Loro Piana’s flagship model, the Open Walk, is well-known to loyal customers. However, what might be news to you is the company’s winter edition, lined with luxurious cashmere and equipped with a slightly more rugged sole. Priced at $1, 100 USD.

2. CQP, Plana Dark Brown Suede
Swedish footwear brand CQP continues to impress with its innovative releases. The Plana model offers a blend of casual style and elegance, featuring a sturdy black rubber sole. Priced at $340 USD.

3. Drake’s, Crosby Moc-Toe Chukka Boots in Tobacco
British brand Drake’s unveiled the Crosby model nearly five years ago, but it truly garnered attention when Daniel Craig sported them with a casual cotton suit in the latest Bond film, “No Time to Die.” Priced at $405 USD.

4. Clarks, Desert Boots in Sand Suede
The original chukka boot hails from Clarks and is recognized for its relaxed vibe, rounded shape, and crepe sole made of natural rubber. It may be the most affordable option in the lineup, but is it still the best? That’s for you to decide. Price: $165 USD.