They’re the epitome of smart-casual, but how do you work Chelsea boots into your wardrobe?.

This week, we turn our attention to foot(wear) paths less trodden with a question from an Instagram follower about the Chelsea boot. Neither particularly formal nor casual, this sharp shoe can be a tricky thing to work into one’s wardrobe in comparison to, say, the trusty Derby or Oxford. Yet, with its origins in Victorian Britain, and made popular again in the 1960s by The Beatles and The Rolling Stones, it’s a classic style that can give you an edge. Below, our US editor tells us how to make it work.

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How to style Chelsea boots?

edwarrrd.jiang, via Instagram

We feel very comfortable around anything that was cool in the 1960s, and there is ample imagery from which to get some styling inspiration. Not that you necessarily want to go full Blow-Up in a pair of Chelsea boots. Or do you? Anyway, something to keep in mind when picking up a pair of boots is the width of the welt – the bit that the sole will stick out from the perimeter of the upper. Generally, the wider the welt, the more rugged-looking and less formal the boot. Because of its single-cut shape, a Chelsea is already going to cut a rather elegant silhouette. You can totally ride it in that direction, with a calf or even patent-leather boot and the leanest of welts for a formal, even black-tie vibe. In this case, make sure your trousers are similar in colour and tapered nice and lean with little, if any, break. On the other hand, if you’d like a pair of clompers to wear with your favourite jeans, pick out a nice suede boot that will develop some patina. Again, keep the trouser leg lean, but leave them a tad longer so that you get a nice little gather (not quite a puddle) of pant around the ankle. We’d opt against a turn-up, for width’s sake, but, as with everything, experiment and season to taste. Now – time to hit the town.

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