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5 Ways How to Wear Ankle Boots

In anticipation of the Fall Fashionista Event, we’ve learned how to wear ankle boots! Thanks to Cobb Hill Shoes for the amazing pair of Ankle boots for this adventure! All opinions are our own. 

How to Wear Ankle Boots in 5 styles

 Autumn has finally found us! The plants are changing color and the leaves are beginning to turn. The temperature is also starting to drop. That means it is time to put away the sandals and pull out the warmer shoes! And this year I just had to get some ankle boots to fit with my fall fashion looks!

I have wanted ankle boots for a long time. I have a huge fetish with boots. I just love dress boots. And while my fetish isn’t as bad as my obsession with dangle earrings, it is still pretty bad. I often find myself stopping on the street to gawk at the newest boots in the department store window. Or even a little drool escaping as I dream of how I will style my looks with the newest pair of boots I see online. Yes, I love boot season!

So I finally got myself a pair of Sienna Ankle boots from Cobb Hill. The Sienna is a feminine ankle boot that gives a sleek nod to motorcycle styling. The wraparound strap is punctuated by an antiqued buckle and metal rivets.

How to Wear Ankle Boots | Fall Fashionista event Sponsor Cobb Hill

It also features a comfortable 2″ heel (cause we all know how much I obsess over comfort meeting fashion on level footing). And it flaunts a convenient side zipper and adjustable ankle shaft that are guaranteed to get your feet excited.

So I finally got my new ankle boots. And I’ve been loving them. Until I hit the question, “How do you wear ankle boots?”

I’ve been playing with a bit of different looks and doing my research online. There are a lot of different ways you can wear ankle boots! And it has me quite excited that I will be wearing the Sienna ankle boots quite a lot this season!

How to wear ankle boots

Style 1: With Jeans. The first style was from my years of life in Wyoming. You wear boots with jeans. It’s a given. Ankle boots are great for wearing with jeans because htey don’t overheat your legs like longer boots do. But they still give that great boot look peaking out from under the pant legs. And it offers a much more comfortable feel.

How to Wear Ankle Boots in 5 styles How to Wear Ankle Boots in 5 styles

Style 2: With leggings. A another great style is wearing leggings or skinny jeans the ankle boots. Anything that is tight around the ankle so that it will tuck easily inside the ankle boot, so you can flaunt the look of the boot.

How to Wear Ankle Boots in 5 styles How to Wear Ankle Boots in 5 styles

And I don’t care about that “no browns with blacks” myth. I have a lot of great outfits that blend black and brown in the designs of the tunics or dresses. So when I’m sporting those the black leggings with these Sienna Ankle boots are perfect way to blend that together even more!

Style 3: Short leggings. Another great style that I can’t pull off, but is a great look for ankle boots is to style them with leggings or skinny jeans that are just a little short. Having a gap of skin between the pants ending and the ankle boots beginning is a great way to give your legs a more slender look. Especially the ankle. It draws more attention to your slender ankle and really lets the boots shine. If you don’t have short leggings or jeans, you can always roll the cuff up on your skinny or straight leg jeans to give the same look.

Style 4: A dress/skirt. One of my favorite ways to wear ankle boots is when I am dressed up. I’ve always been a fan of my feet being comfortable when I’m dressed up. So I love that ankle boots style great with skirts and dresses of all lengths. Long and short. They all look great with a great pair of ankle boots!

How to Wear Ankle Boots in 5 styles

How to Wear Ankle Boots in 5 styles How to Wear Ankle Boots in 5 styles

Style 5: Tights! No joke. Tights look great with ankle boots. They are so slim to the leg that they don’t add a lot of bulk around the ankle. And if you are looking for a warm look; it is a great way to wear up while still showing off the sexy ankle boots you just added to your collection! Plus it is a great way to throw in some extra color this autumn too! This is best pairs with a shorter pencil or A-line skirt that reaches about knee length.

How to Wear Ankle Boots in 5 styles

Ankle boots offer just enough hint of country but enough chic to complete any look. Depending on the outfit you wear you can pull off a country look or a city look, all with the same pair of ankle boots! They are a great piece to have in your closet collection because they are so universal in creating great fall fashion looks!

If you are looking for a great pair of ankle boots to complete your fall fashion look, definitely check out Cobb Hill! I adore Cobb Hill shoes because they are quality that is built to last! My last pair of Sadie shoes are over 1.5 years old and they still look amazing. And I have worn them all the time! That is why I’m honored that Cobb Hill is our sponsor for the Fall Fashionista Event! Come back October 9-17th and you will have a chance to win a pair of Cobb Hill shoes of your choice from their entire website! That’s right, any pair of Cobb Hill Shoes! Go ahead, start ogling now!

How to Wear Ankle Boots in 5 styles


What is your favorite way to wear ankle boots?

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