The chukka boot is a menswear staple, casual AND dressy at the same time. Being a shoe originally worn by polo players (where "chukka" is a period of play), they rose to fame in the 40's. The popular "Desert Boots" are derived from them.
You can wear them with chinos, jeans or chords. They might work with a suit as well, but keep in mind, they are more on the casual side of style ;)
The suede version is one of the most popular ones for this particular shoe style. Since these are easy to maintain, you might wanna wear them when clubbing...
They also come along in shell cordovan leather.
With a water resistant upper leather (shown: Alden Chukkas with so called "kudu leather", a heavily oiled leather) and a rubber sole, you can even wear them in winter.
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