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Do’s and Don’ts of Cuffing Your Jeans with Ankle Boots (Part 4)

You made it to the final installment of Cuffing Your Jeans with Ankle Boots! Part 1, Part 2, and Part 3 covered how to cuff your jeans with classic ankle boots, short ankle boots, and dipped front ankle boots. So for Part 4, let’s talk about tall ankle boots. These have become increasingly popular in the last year, and many of you probably own a pair. There are some rules that are slightly different depending on the heel height (flat boots and 4-inch heel boots are not created equal), but we’ll cover that as we go along.

First up, for those tall ankle boots, don’t tuck your jeans in. This is not ALWAYS the case. For my pair, no, I shouldn’t tuck them, especially because you can see the jeans through the cut-outs. But if your boots are flat and tall, like this pair from Gap, tucking is okay. But for dressier and heeled pairs like mine, skip the tucking. Also DO NOT put your jeans over the top of these boots unless they are flared and long jeans.

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For the last three installments of these posts, I’ve talked about the importance of showing off your ankle when wearing ankle boots. But for these tall pairs, the rules are slightly different. For these tall and thin boots, like mine, your ankle doesn’t need to show. The boot itself is elongating your leg, especially if it’s in a neutral color like brown or gray. So since you don’t have to show your ankle, the following photos are a few good ideas for cuffing your jeans with this style of boot. Instead of a cuff, try bunching up the bottom of your skinny jean so it sits nicely on top of the boot shaft. It’s a perfectly casual and slightly undone look that I really love.

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Another alternative is the single cuff. This one cuff helps break up the line of the leg and creates a little space between the shoe and the jeans that your skin usually does. No skin showing here is necessary … have your cuff sit right at the top of your shoe and you’re good to go!

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This style of cuffing will look good depending on your style of boot. Experiment with yours and see if the tall cuff works with your boot. Typically it works better for a heeled boot, rather than flat.

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Whew! Did you make it through all four parts?? If you have any questions about your style of boots, please ask away! Happy boot wearing and cuffing!

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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