How to Wear Ankle Boots (Plus COMFY Options)

Throughout high school and middle school, I was on the pom pon squad.

Why is this important? Because my knees are completely shot. All those years of pounding on a gym floor left me with knees that can’t handle the gorgeous high heels that I love for more than a couple of hours. Most athletes seem to develop similar problems later on in life, but hey- I try not to sacrifice style when selecting kicks! I need comfy shoes if I am with my kids and ankle boots are the perfect choice (you won’t see me in heels if they are in tow).

My favorite trend this fall, and one I firmly believe will last, is the moto/ankle boot trend. I love pairing these with leggings and a skirt, tights and a dress, skinny jeans, you name it, I can figure out a way to work my motos in. These are my 3 most popular ways:

With a skirt/dress and leggings/tights: Make sure you don’t have elephant ankles (saggy, baggy material around your ankles). Yes, your leggings can be cropped above the ankle, but please don’t do capri leggings! IMHO, capris should be banned. Yes, I said it.

A skinny cuff on slim jeans: Do a double or single roll only; any more and this looks bulky and sloppy.

A wide cuff on slim jeans: This is more of a hipster look, and you can cuff it fairly high. Just keep the peek of skin to about an inch.

BUT PLEASE FOR THE LOVE OF ALL THINGS HOLY/STYLE DO NOT DO THIS; it looks like your jeans are growing out of your boots, like you are wearing denim tights.

***UPDATE- I have had a few comments on this…if you LIKE this style, then by all means wear it! In the words of Salt N Pepa “Opinions are like assholes, and everybody’s got one.” This is just my asshole opinion 🙂

There are a couple of options when selecting shoes that allow you to wear them ALL day long without limping. Since my two preschoolers still like to be carried on occasion (ugh, 70 lbs of child puts a LOT of strain on my poor bod), I need shoes that are up to the task.

Tip: Grab no show socks in the same color as your boots, not nude. Nude rarely blends perfectly with your skin and kills your look when it shows.

First, you can grab any old boots and pop in orthotic inserts. I am SO down with the Dr. Scholl’s kiosk that is in my local Walgreens. When I am waiting for my prescription to be filled, I hop on the FootMapping gizmo and figure out what my issues are and what inserts I should buy. (And no, they aren’t paying me for this…I just think it is genius). They aren’t cheap, but they are tailored to your individual issues and you can get a $10 rebate here. Just make sure you have enough wiggle room in your boots for inserts because they can crowd your tootsies. Bonus: you can use these in multiple pairs of shoes.

Second, if you just want a pair of boots that have built-in support, check out a few options below. Here are the brands that truly focus on comfort and support. No, their boots aren’t cheap, but they aren’t cheaply made either. They will last for years to come.

Vionic: Their supportive technology was developed by a renowned podiatrist and founder of Orthaheel Technology.
Sofft: Features latex footbead and arch cushion as well as dual density cushioning in their extra foam padding.
Børn: They have been in the business for over 20 years, and their shoes feature an arch cushion, air diffusion layer, and dual density foam cushioning in the foot bed.
Birkenstock: Their classic German footbeds mold to your feet and are made from resilient cork and natural latex.

Here are my top picks for comfortable moto ankle boots! Shop via the Maven board below and see my notes for each bootie. I am wearing the Vionic boots in the photos above, and they are AH-MA-ZING.

Disclosure: This post may contain affiliate links, but they do not affect the price you pay.