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...
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
cardigan [size down one, wearing an XS] // tee [true to size] // jeans [true to size] 
wedges [true to size] // necklace // purse
baseball tee [true to size] // jacket [size down one, wearing an XS] // white jeans [true to size] 
floral tunic [wearing a medium] // ankle booties [true to size]

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]
shoes [similar] // choker 
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]
maxi dress [true to size, wearing small] // wedges [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...
top [true to size, wearing a small] // pants similar // ankle booties similar // purse

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 - several of you asked about the whole sock situation. If they have cutouts or openings on the sides, obviously socks aren't going to happen. I have discovered Foot Petals which you can put in the bottom of your shoes when not wearing socks and they are breathable plus can be taken out and washed in the washing machine which is awesome. For more information on those you can see my blog post here. Now, if they are ankle booties that don't have any cutouts or openings on the side, you can wear short little socks. Make sure they are the "no show" kind that you can't see - you can find several different styles here. Due to not typically wearing socks that will cover your heels, a few of you expressed concern about your heels rubbing the back of the booties. Thankfully there are these Foot Petals Heavenly Heels that will prevent rubbing!

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

2. Additional tan + colors under $100

3. Black and grey under $100

4. Tan under $200 

5. Grey under $200

6. Black and grey under $200 

Hope you found this beneficial! As always, thanks for stopping by - now if you'll excuse me I have a hot date to chick-fil-a to get to ;) 



  1. Thanks for a great blog post on wearing booties! Here in Pennsylvania, we wore boots with socks from September all the way through something like the second week in May last winter. I love many of the cut-outs you show, but here they're just not a good investment. I also can't see investing in a high-end bootie such as Frye because the slush and salt ruin everything here! However, your recommendations for rolling jeans, etc. are appreciated and all of your outfits look so cute! I'll be emulating some of them as soon as the weather starts to turn!

  2. Love this post...I'm late to the bootie game, but fully embraced them last fall. I have a few go-to outfits, but just got a great Nordstrom dress today that I'm hoping to pair with my gray-ish Sam Edelman booties. Just hoping I can pull that look off (I'm not as young as you are!��).

  3. Thanks! Useful information. Now if you'll excuse me I have some shopping to do😀

  4. Great post! Do you own Navy? I think they are cute but am unsure. Thanks

    1. I don't! I think they could be super cute though! Rock em' girlfriend!

  5. these are all so cute but at 6'0 i can't do any sort of heel! so sad.

    1. there are several great options that are flat! hopefully you can find something!

  6. I'm dying over the Rozina booties. I want black AND brown. Ugh. The problems!! Do you have a suggestion either way? Do you love & wear them all the time? Please help me rationalize (or not) this purchase.. :) Thanks!

    1. I do love them and wear them all the time! I have a lot of brown shoes which is why I went with the black, however either are great options (you can't go wrong with whichever you pick!) Here's a thought! You could get the black and then these brown are on sale (same brand/style, just not cut out): http://bit.ly/2bWaeOR

  7. What advice do you have on shaft height? (Lol, but for real.) I am 5'5 but have a long torso and shorter legs, ankle length jeans in a 27-28 inseam are regular on me and crop length of 25-26 work great as ankle length on me. I have a few pairs of ankle boots but they all seem like they come up to high on my leg and then when cuffing the jeans to get them up there my legs look even shorter. And advice on how high up on the leg/ankle the booties should go?


I read and appreciate every one of your comments. Thanks for stopping by my space and sharing a piece of yourself on this huge ole internet. I meant that in the least creepy way possible. I'm just good at making everything awkward. Anyhow, thank you for your comments. They make me smile :)