Good ole ankle booties - my love for these babies runs deep as I've been a fan and wearer or this boot trend for a couple of years now. While I embrace them and love them now, it did take me a while to get comfortable with how exactly to wear them, what to wear them with, how to wear my jeans with them, whether or not I could wear socks with them and the list goes on. Because I've had a journey with them, I am going to go out on a limb and assume that maybe you too have questions on how to best wear them or are in need of some great quality options at a reasonable price point.
Well guess what ladies and gents [okay, just ladies] today I'm bringing you all of that information, my favorite looks on how to wear these and more. Because we have A LOT to cover I'm going to shut up and get started.
First - the number one question I've had around ankle booties and what the majority of you have been asking is "HOW IN THE WORLD DO I WEAR JEANS WITH THEM?!" except you weren't actually shouting it but for dramatic purposes I thought I would. Do you cuff them, do you tuck them, do you need cropped jeans, what ever do we do with them? Here's my two cents on how to wear your jeans with ankle booties:
1. General rule of thumb, do not tuck. Go to great measures before resorting to tucking. Those great measures being...
2. Buy either cropped ankle length jeans [see my post all about jeans and learning your inseam] or
3. Cuff or roll up your longer jeans to pair with these.
Your jeans should hit above the top of your booties so whatever you gotta do to get your jeans up there, do that. First lets look at ways to wear cropped jeans with booties - my favorite cropped jeans for ankle booties are these, these, these and these. One thing to note - you don't want too much of a gap between your jeans and the booties so be mindful of that. Here's a few looks with cropped jeans and booties.
ps. for reference I am 5'4, prefer a 25-27 inseam for cropped jeans and typically wear a size 26 waist.
cardigan [size down one, wearing an XS] // tee [true to size] // jeans [wearing a 26, if in between sizes go up - I rolled these down one roll to create a little more length due to my booties not having much heel and height] ankle booties [true to size] // purse
Next lets tackle the regular jeans that you cuff - my favorite ones to wear with booties are these, these and these. I typically do one larger cuff with my ankle booties although you can also do 2 smaller rolls or cuffs if you prefer that look. Here's several looks showcasing how to wear them with jeans...
cowl neck sweater [true to size, wearing a small] // jeans [true to size] // ankle booties [true to size]
tee [true to size, wearing a small] // jeans [true to size] // jacket [size down one, wearing an XS]
cardigan [size down one, wearing an XS] // tee [true to size, wearing small] // jeans [true to size]
lucky ankle booties [true to size] // pink top [true to size, wearing small] // lace up sandals [true to size]
cross front top [true to size, wearing small] // jeans [true to size] // lace up sandals [true to size]
vest [true to size, wearing small] // tee [true to size, wearing small] // jeans [wearing a 26, if in between sizes go up] // ankle booties [true to size] // purse
A few of you wanted to know "what else can you wear them with besides jeans?!" Well friends, let's take a look....
First we have dresses....
dress [older from miss chic] // cardigan [size down one, wearing XS] // lace up sandals [true to size]
Then we have shorts...
long sleeve tee [true to size, wearing small] // shorts from target - available in store // black wedges [true to size] // cross front top [wearing a medium] // ankle booties [true to size]
We have colored denim....
sweater [true to size, wearing a small] // jeans [I sized up one to a 4, not sure if that was necessary but my other rockstar jeans shrank so we will see if that was a good call or not] // ankle booties [true to size // purse
We have underneath work pants...
And last but not least, we have with tights underneath skirts or dresses for work [this is typically all I wear in the winter to work!]
tunic [size down one, wearing an XS] // skirt from stitch fix [similar here] // booties similar // purse
PHEW. Do we all have a general idea of different ways to wear ankle booties now? Lord I hope so because I don't think I can take one more mirror selfie.
Next up - let's talk about what seasons ankle booties are appropriate. For those of you who are lucky enough to live in places that don't receive snow or terribly cold weather, it's game on for you year round. For the unfortunate [myself included] I turn to different styles of ankle booties depending what season we are in. If they are open toe or have openings/cutouts I will wear those through the warmer months and fall. As soon as winter hits those go to the back of the closet and I bring forward the ankle booties that are fully enclosed. You can still definitely wear them, you just won't want to wear the more exposed styles in the dead of winter. One thing to also keep in mind for winter is the material - for ankle booties that I know I will be wearing during the cold, snowy months I try to buy leather. For the fall or warmer months, I love suede. Snow and suede don't always mix well so just be mindful of that, unless of course you are treating your suede beforehand [more details on how to do that here].
When thinking about which booties are right for you, fit and comfort is so important. After wearing different brands and styles, my go-to for comfort, looks, price and fit are Vince Camuto, Lucky Brand, Sam Edelman and Jeffrey Campbell. You definitely get what you pay for and when it comes to booties that you want to wear for more than one season that won't kill your feet, paying a little more is more than worth it.
Last but not least before we dive into all of my booties finds, two last things to consider are color and heel height. If ankle booties are going to be a staple in your wardrobe I would suggest starting out with a great pair in the beige family. Tans are so versatile and can be paired and worn so many ways. Other great colors to have on hand are black and grey. It is fun to have a pop of color if that's something you want to experiment with. In regards to heel height - that is going to be a personal preference. I prefer either flats or those with a 3" heel or less. Wedges are another style that are super comfortable for me and easy to wear.
I think that covers every possible thing under the sun when it comes to ankle booties - if I left something out or you have questions please let me know. Below you can find my favorite styles broken down by price and color - it may take a minute for the images to load so patience. Once they load you should see a little + on each pair - when you hover on that it will show the price and then you are able to simply click on the price if you want to be taken to the direct spot to buy! Remember if you like a particular style to click on it because there is a good chance that it will be offered in several different color options as well! Happy ankle bootie shakin it up!
1. Tan under $100