Kicking off my what every guy needs series: Every guy should own at least a single pair of Chukka Boots. The chukkas and desert boots look a lot alike (similar heritage) but chukkas are the more adaptable.

Chukka boots get their name from polo – a chukka is a period in that sport. They’re a two- or three-eyehole ankle-high boot like the dark brown ones pictured above. They can be made in anything from canvas to shell cordovan, it’s their form that makes them chukkas. Desert boots are a specific subset of chukka boots. Like chinos, their popularity stems from WWII soldiers (and surplus-sellers) bringing them home from the war, and the emergence of casual style in the 1950s. They’re based on the boots worn in desert campaigns by British soldiers. They always have crepe rubber soles. [from Put this On]

While they are primarily “casual” boots, they are extremely versatile, especially if you work in say creative or technology industries. And I do. When worn with dark jeans and a simple white shirt, they help give a sense of feeling dressed up. Jeans and plaid shirts – they are great for looking (and more importantly feeling) casual. Wear them with simple chinos and they make the whole attire look casually formal. The chukkas make formal pants a little less formal and give a touch of whimsical. Chukkas are what you buy when you are ready to chuck your sneakers – or at least stop wearing them to work.

There are many different varieties of chukkas and they come in a range of materials and prices. I like the ones made from suede, for the full leather chukkas are too formal for my taste. I recently bought a pair of suede chukka boots from Alden, a company that makes high-quality shoes that last nearly a lifetime. I love this shoe because it works well during the warmer months as the shoes are unlined. They are fairly priced – about $450 – and are of extremely high quality. There are other more (or less) expensive brands such as Church’s and Cole Haan. Also check out New York-based Leffot — they got some really good (though expensive) brands including the Aldens.