Date Night · Dressing for the office · Shoes

A How-To Guide to Ankle Boots

The single question I get from friends and family above all others is “I love ankle boots, but I don’t know how to wear them!” For all others out there who have similar frustrations, this post is here for you! I am a huge fan of ankle boots and am well-versed in the art of wearing them. The wide world of ankle boots can be confusing and overwhelming so I am going to do my best to simplify it. In my mind there are 3 types of ankle boots: flat, heeled and dressy. And, believe it or not, all 3 can be worn with pants, skirt OR dresses. So really, if you have 1 pair of each type, you are 100% set on ankle boots. A few rules before I dive in:

1. Opt for neutrals – black, taupe or cognac. Colors or patterns can overwhelm even the most experienced ankle boot wearers.

2. Stick with boots that don’t go beyond about 2 inches above your ankle bone. I don’t know who decided that mid calf boots were fashionable, but I am not a fan. However, if you are a fan of this look, please disregard this advice 🙂

3. Take chances! The only way to know if you like a look is to try. So don’t be afraid to try a combo that seems wrong or scary. If you like it, you will pull it off! [Like Ted’s red cowboy boots. I hope many of you get this reference.]

Nowwwwww onto the good stuff. Let’s start with flat – these are best pair with a casual look. Jeans, casual skirts and everyday dresses. Flat ankle boots are super on trend. I’m going to use 2 pairs that I actually have as examples:

1. These by Sam Edelman. Big fan of these – I took them to London…and they hurt my feet. But even my tennis shoes hurt my feet so I don’t think that is measure.




2. These aren’t exactly the same as mine, but they are close. DV by Dolce Vita. (Extra 30% off in black!)



For pants – wear these with skinny jeans for sure! Be sure to roll up the pant leg of your jeans UNLESS you are wearing leggings or jeggings. If you try to tuck them in, they will likely be all wonky and not really fit into the shoe.

Flat Ankle Boots - Jeans

For skirts or dresses, just ensure the styles are pretty casual. Wool mini skirts and day dresses will do the trick!

Flat Ankle Boots - Skirts&Dress

Onto heeled boots – these are great because they can definitely be casual OR dressy. And look great with any leg style of jeans. They can be worn to work, on dates or casual weekend outing. These are my favorites – and I only need 1 pair of versatile heeled boots by Steve Madden to illustrate 🙂


With pants – This style looks great with bootcut jeans [contrary to popular belief, skinny jeans aren’t the ONLY type of jeans to wear! I still rock my bootcut :)] but also with skinny. Roll your skinnies to just above the top of the boot, as with the flat boots.

Heeled Ankle Boots - Jeans

These boots can definitely be  dressed up for work – try a sheath with tights and the boots. And they definitely work with a pencil skirt!

Heeled Ankle Boots - Skirts&Dress

Finally – dressy ankle boots. These are best for events – fancy night out with your significant other, cocktail party, winter wedding. I have a pair of Via Spiga boots very similar to these and love them! Find a pair with a platform to make them wearing for a long night of festivity [and alcohol!].


If you wear these with pants, no need to roll them! Just ensure that the jeans are skinny enough that they smoothly fit into the ankle shaft. Be sure to pair your dress with tights – black tights are very chic!

Dressy Ankle Boots

Well, have I cleared up the great ankle boot mysteries?! Did I miss out on any?

The holidays are coming! Kate Spade, Sephora and Nordstrom have already put together their gift guides. So look for my annual gift guide in the coming weeks!


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