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Octavia High Top Sneaker

While you may not be completely ready to trade in your summer sandals for a pair of fall boots, you've gotta admit that sifting through the new season's shoe selections is kind of exciting. Loeffler Randall's Octavia High Top Sneaker ($250), for example, is a bit of a hybrid shoe; part leather ankle boot and part thick-soled sneaker. You can wear these cap-toed shoes with just about anything, from colored skinnies to denim minis.

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