The Chukka is just one of those versatile styles you don't need to question, its versatility allows it to be worn with pretty much everything and its a style that works all year long. Oak Street Boot Makers is has got a new Chukka they're debuting exclusively on Bonobos and this is definitely one to put on the list.
Their Desert Chukka is handcrafted in the USA and features Goodyear Welt Construction and the upper is made from a waterproof Natural Roughout Horween Chromexcel leather. A nice option if you love crepe sole Chukkas, but want something that holds up better to the elements.
$425, available at bonobos.com