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The Do’s and Don’ts of Cuffing Your Jeans with Ankle Boots (Part 3)

The last few days I’ve posted Part 1 and Part 2 of the Do’s and Don’ts of Cuffing Your Jeans with Ankle Boots. We’ve made it to Part three, and this time we’re covering how to wear dipped front ankle boots. The pair I have has a taller shaft with a dipped front, but there are a lot of other pairs out there that are shorter at the ankle and then dipped in front, like this pair from DSW. But whatever height your dip is, these are the types of boots we’re talking about today.

In Part 2 I talked about how the reason it’s important to cuff your jeans when wearing ankle boots is because these types of shoes cover up your entire foot and can make your legs look stumpy if you don’t see any of your leg. Some dipped ones show a little more of the top of your foot, so some pairs can be worn without cuffing your jeans. So this first picture is a “wrong,” but if your shoes have a super low dip that shows a big section of the top of your foot, then you’re okay to wear your jeans uncuffed. It’s a case by case situation, so try yours on and experiment with uncuffed and cuffed jeans. In my case, they have the dip, but the top of my foot is still not showing because the dip is not low enough, so uncuffed jeans do not work here.

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Since these boots have the dipped front, you don’t need your entire ankle to show to achieve your goal of elongating your legs. Just a small half circle peeking out is enough, as shown. So cuff up at least a little bit so you can see some skin.

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Don’t ever pull your skinny jeans over your ankle boots. The only reason your jeans should ever go over your boots is if they’re long and flared. Otherwise, if they’re straight or boyfriend or skinny, cuff them up and show off those ankles above your boots.

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Rolling your jeans is another good alternative if your jeans are long and a single cuff isn’t enough to show off any of your ankle. The most flattering look is when the bottom of the cuff touches the top of your boot, as mine does. However, this is only the case with taller boots, like mine. Short “shooties” should not touch the bottom of your jeans if they’re cuffed because it makes your legs look stumpy.

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Alternatively, if your boots are tall, like mine, and you cuff your jeans too high, it also makes your legs look stumpy and throws off the proportions of your leg lines. So don’t leave a big gap between your shoes and jeans, but leave a little gap. A little experimenting will help you get the right proportions for your particular pair!

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