While saying adios to summer can be a drag, I love preparing for the cooler months that will soon be among us. My addiction? Boots – boots of all varieties, and this year won't be any different. One boot that made a premier comeback last year was the over-the-knee or thigh-high boot. You can dress this boot over leggings, jeans or with a skirt (like this Fashionista did). Try a heel for dressier occasions, but regardless, they are a super chic and very wearable item this year. Another type to watch out for is the bootie. I've seen several adorable versions on the shelves already, and they are perfect paired with tights.

To get the most wear out of your new boot, pair them with a skirt (sans the tights) now, and add the pants when the weather cools down. Plus they will transition well into winter—just remember to treat them for the famous Oregon rain!

Hint: Try these over-the-knee Frye boots great with jeans and skirts, or, for a more affordable and versatile type, try these black flat boots by Rampage.

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