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How to Style Your Pencil Skirts and Dresses with Ankle Boots

Ankle boots are one of those pieces that can be tricky to style, depending on the shape and cut of your boot; the shape, height and width of your leg; and also the clothes that you’re wearing with them. I’ve created a whole series about how to style different types of ankle boots, starting with wearing them with jeans here, here, here, and here, and then wearing them with your A-line skirts and dresses here.

Now let’s talk about those pencil skirts and dresses that hug your curves and end right around your kneecap. Should you wear them with ankle boots? Why or why not? Let me show you three pairs of my ankle boots, and tell you how to best style them with these hip hugging skirts and dresses.

For your low-cut or lace-up ankle boots, you can definitely combine them with your pencil skirts and dresses. The most important thing about ankle boots is making sure they flatter your leg line. So with low-cut boots, the smallest part of your ankle is visible, and with pencil dresses, the thinnest part of your leg (just below your knee) is visible. This style of boot, even if it doesn’t have much of a heel, will keep your legs looking long and lean.

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Tall ankle boots can get tricky, so let’s talk about when they do work and when they don’t work. Tall ankle boots can cut off the line of your leg and make them look stumpy, so be careful when wearing them with skirts. These ones don’t cut off the line of my leg because they’re neutral in color (making my legs look longer) and they have cut-outs, which gives a little glimpse of my ankle and keeps my legs from looking cut off.

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These ones below don’t work as well because they are a dark color and create a very stark line on my leg, making the bare section of my legs look very short and stumpy. If your boots are lighter in color, the dip at the front of the ankle boot can be helpful in elongating the leg, but in this case it doesn’t help much. Make these work by throwing on a pair of dark tights so the contrast from boot to leg is very subtle!

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Find more of Merrick’s style and writing at Merrick’s Art

You can also find her on Facebook and Twitter

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