Finding over-the-knee boots is a task that I, like most shoppers, dread: It’s so hard to find boots that actually fit real calves when you’re not Karlie Kloss’s height. So when I found out about Stuart Weitzman’s new “Ultimate Boot Guide,” I thought I’d give it a try; it allows you to compare which kind of boots will give you the best fit, and the pros and cons of each. The customer chooses the color, material, sole type, toe shape, and heel height to determine not only the kind of boot you like best, but the kind you actually need. For that kind of luxury, you’ll have to pay more than you would for the average fast-fashion shoe, but it’s worth it to have boots tailored to your lifestyle. Just think how smart you’ll feel when you’re not hobbling around with sore feet this winter, or throwing out a battered pair of boots after one measly season.
And contrary to popular belief, when styled correctly, over-the-knee boots can elongate your legs and provide extra warmth on cold days. The trick is to balance out the proportions of what you wear with them — whether it’s a simple sweater and slim-fit jeans that will tuck into the boot seamlessly, or a chunky sweater dress and jacket. Scroll down below to see the best picks.
With a nice suede Bordeaux finish, this boot really says “It’s fall” in an elegant way. The signature-stretch suede molds to your legs without suffocating them, and the tie-back detail lets you adjust the length at the top of your calves.
If you’re looking for a practical boot that looks as sleek as its six-inch counterpart but has the comfort of a kitten heel, we’ve found it. The front panel is made of suede, but the back consists of micro-stretch elastic, which makes it super comfortable. And the best part? The heel is only three inches, so you can wear them all day and night.
Flat boots that elongate your legs? It’s possible when made with the right materials, as is the case with these thigh-high stretch and suede boots in a cool navy blue. The material resembles leggings, but contours your legs in a flattering manner.
The Highland boots are by far the sexiest pair on this list, and make for a good option when you want an over-the-knee boot that hits your mid-thigh and gives you some height.
A combination of trendy and practical, the LeggyLady boot in velvet feels timely for fall and the holidays, but will also fit into your existing wardrobe with ease. There’s not a skirt, dress, or pair of pants it won’t complement.
Dubbed the most “leg-lengthening” boot because of its mid-height heel and mid-thigh length, the TieLand boot has a nice natural suede tone and a block heel that feels fresh.
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