Ankle boots are probably the most versatile footwear a man can own and we say this having tried to argue for various other options over the years before eventually conceding that nothing else quite covers the same range of situations. They work with jeans of almost any cut because the shorter shaft doesn’t compete with the trouser. They work with chinos and smarter trousers in a way that feels more interesting than a standard dress shoe without being obviously casual. They work with more relaxed outfits without looking like you’ve overdressed your feet. The key variables are the heel height and the toe shape. A slightly chunky sole with a rounded or almond toe is more wearable day to day than a very flat sole or a pointed toe which is more specific in the outfits it works with. Start with something in dark brown or black and build from there.