A little bit Beatles, and a lot model off-duty, the Chelsea boot has long been a wardrobe staple. We’ve always gravitated to Chelsea boots due to their easy wearability, and love that they come in enough styles to justify owning multiple pairs (rain boots, $130, and faux-fur lined Doc Martens, $190? Sold).
So, as we enter into boot season, we scoured the market, reviewed plenty of pairs and talked to two experts to determine the best Chelsea boots for women. Whether you’re looking for the warmest pair to finish off your head-to-toe urban explorer look in the depths of winter (we’ve got the warmest coats covered here at PureWow, too), or need Chelsea boots that are a cinch to pull on and off in the TSA line, the picks below will get your shopping list off to a fall-worthy start.