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The real question is: What can’t you wear with ankle boots?

As one of fall’s must-haves, ankle boots/booties can be paired with a huge variety of different looks. The versatility of the ankle boot is perfect for the season. If you’re headed to school and want to be casual or you’re going out for a dinner date, ankle boots can be the perfect shoe to complete your fit. Whether flat, cut out, wedge or heeled, say hello to ankle boots this season!

ankle booties

One of my favorite pairs of ankle boots, is the cut out. It’s a great summer to fall transitional staple and looks good with pretty much everything. I prefer black leather, but I’ve seen cut outs executed well in various colors. Rock a pair of cutout booties with a sweater or t-shirt and finish the look off with a statement necklace.



I love pointy toe booties! They’re so sleek and sexy and can be worn from day to night. This Burgundy pair from H&M is a great color and can be worn with a pair of black jeans and leather jacket and wide brim fedora if you want to be casual. For the night, this would look great with a pair of cigarette pants and a simple blouse.

Ankle boots also go well with shorts. And if you’re thinking, “but it’s fall, I can’t wear shorts now,” know this: you totally can! Before it gets too cold, throw on a pair of shorts with stockings and a cute pair of ankle boots. Seal the deal with a heavy knit sweater or cardigan and a denim top.


Lastly, when you feel like sporting a laid back look with your ankle booties, opt to do so with a pair of boyfriend jeans, cropped sweater and parka. As always, you can add the finishing touches with a chain or hoop earrings!