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Save Steal Splurge: the Riding Boot

You know the drill. Even if you’ve got a pair of boots that you love one fall, when next fall comes around, you get the itch to update. We get it, because although the beloved Stuart Weitzman 50/50 is an investment, sometimes you’ve just got to get something shiny and new. So this season, we’ve picked out some of our favorite tall boots — all with a little bit of equestrian edge. And as a bonus, two of our picks, the Chinese Laundry boot and the Cynthia Vincent option are great for those with a little more of an athletic calf.

So as the weather cools down, slide into these great boots for an instant seasonal update.

Save: Chinese Laundry Fallout ($89.95)

Steal: Steve Madden Ryperr ($170)

Splurge: Cynthia Vincent Hamilton ($495)