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How to Wear An Ankle Bootie

    I was late to the ankle bootie party. When they first came into fashion a few years ago, I thought they were odd looking and I had no idea how to wear them in my regular work-at-home mom life.

    Last fall, I finally came around and bought my first pair.


    As with most new-to-me trends, it takes a few times wearing an outfit that feels awkward and forced before it becomes comfortable. The first few times I wore these booties, I didn’t know quite how to wear them. Do you cuff your jeans? Or double roll them? What kind of socks? Can you wear them with a dress? Bare legs or with tights?  I really wasn’t sure.

    If you look around on pinterest or in magazines, you’ll find countless examples of bootie-wearers. Some outfits are great and mimic-able for the everyday; many are not.

    So since I’m a busy mama who likes to look cute, but doesn’t work too hard at putting together fancy or unrealistic outfits, I thought I’d share with you my thoughts on how to wear an ankle bootie. If you haven’t taken the bootie plunge, perhaps these simple suggestions will win you over.

    How To Wear Ankle Booties / jones design company


    This is the way I wear my booties most often. I appreciate that the chunkier boot adds balance to a skinny jean that tapers down (balancing out the hip/thigh region). I find booties are often times more comfortable and casual looking than skinnies paired with tall boots (although still a look I like).

    To wear, cuff once or roll twice to expose just a bit of your ankle.

    With slightly taller ankle boots, there’s no need to cuff – just tuck your jeans in like you would tall boots. This will elongate the line of your legs which is always a plus.
    rolled skinny jeans + liner socks + ankle booties / jones design company

    SOURCES:  skinny jeans / old navy liner socks / toms wedge booties



    Hooray for bootcut and flare jeans coming back. I suppose they never fully went away, but we’re seeing many more outfits and options with bootcut jeans than we did even a year ago.

    I remember wearing ankle boots in high school with jeans, and this is really no different now. Add height with a heel, or go with flats but just make sure the hem of your jeans hit the base of the shoe. Steer clear of the high-waters.

    bootcut jeans + trouser socks + ankle booties

    SOURCES:  bootcut jeans / gap trouser socks / ankle booties



    Admittedly it has taken me a while to feel comfortable wearing ankle booties with a dress or skirt. Now that I’ve crossed that bridge, I find booties to be a very practical choice for the fall and a great (more casual) alternative to heels.

    Wear bare-legged, with ankle socks (a bit more fashion-forward and probably just for the younger crowd) or opaque tights that match your booties to make your legs look extra long. shift dress + tights + ankle boots / jones design company

    SOURCES:  dress / opaque tights / wedge booties

    25 thoughts on “How to Wear An Ankle Bootie”

    1. You’re the best. Thanks for giving details and multiple examples and saving me the time to looking it all up. I trust your judgment so no need for me to waste my time looking. And apparently I have no time to look because I see ankle booties in the store and think I need to check out this topic before I dive in and well, it’s been months and I’ve yet to do the research. Now I can pin this post and keep trucking on…maybe even in ankle booties one day!

    2. Thank you thank you for this post! I just bought my first pair over the weekend! I too have been on the fence about how to wear! this post helps tremendously!! Now only to get up my confidence to wear with a dress and booties! Not sure this 44 year old mama can pull that off ???

    3. Thank you for this! I have been going back and forth about this look myself and love to see some real life outfits! I’m in love with the sweater + skirt combo!

    4. Love the sweatshirt coat. I remember it from target a while back. Wish I would of grabbed one! Have you seen others that were similar to this one?

    5. They all look great but I can’t wrap my head around boots and bare legs, but that’s just me. FYI, the spare shoes under my desk are black ankle booties!

    6. Emily you look adorable in everything!
      May I ask where you found your button down check shirt & the boots that you paired with the dress? LOVE!!

    7. Any suggestions for flat or low heeled booties? That’s what I can’t wrap my head around and “submit” to my hubbies preferences by not wearing high wedges or heels and towering over him. Any resources would be super helpful.

      1. I just did a quick pinterest search and it looks like you can wear flat booties just the same as heeled ones! Some styles are super cute, too. Now I’m thinking I need some flat ones!

    8. As we used to say in high school, “get out of my brain!” This has been my fashion quand art as fall slowly makes its way into Texas. I love all your suggestions but riddle me this: how do we wear ankle booties with skinny jeans once it gets cold enough outside that a bare ankle is uncomfortable (okay that probably won’t happen in Texas)…do we still roll or cuff and have a cute pair of crew socks peeking out between the top of the boot and the bottom of the Jean? I haven’t seen it anywhere on Pinterest so do I just go for it? I don’t want to be “That 43-year old Mama” that looks like a complete goober. So help me out, oh wise adorable one!

      1. Great question. I think for the most part, my ankles don’t get all that chilly :) But I saw a darling/stylish/younger-than-me friend wearing trouser socks with her booties and her jeans rolled up. The jeans came to the top of the booties, but when she sat, her socks peeked out. They were neutral – almost the same color as her boots. Not sure if that is necessary, but I’ll just copy her.

      2. Hi guys! Emily, this was such a great post! I’m with you about feeling a little uncomfortable when I first tried ankle booties, but now I love ’em. And Brandy, I hear you on the cold ankles—I live in Minnesota and we don’t want ANY exposed skin come January. :) Check out this post about how to wear ankle booties with socks. It is SO helpful (and written by a Texan like you!). Hope it helps!

    9. You are a year ahead of me! Just last week I decided ankle boots are NOT dumb and I can allow myself to wear them… which quickly escalated to I MUST have them, and now you have sealed the deal. DSW, here I come. Thank you, Emily!

    10. I bought your tan boots from an earlier post and love them! Also love your outfit with the skirt and sweater- any links to those? Love following these ideas!

    11. Hi Emily! Can you tell me what color the Kork Ease wedges are? They look like the Morosita Leather, but in your pictures, they look so much lighter. like maybe they are the Desert Leather?

      Thank you!

        1. Thanks for letting me know! I love the distressed look on the taupe — hopefully they will bring it back! I bought the Morosita and I love them; the black are tempting too! Thanks for sharing!

    12. Emily, I really don’t know how you do that: coming up with the answer to the exact same thing I have been wondering about all day. Maybe our minds just work alike?
      I just bought some ankle boots and wore them today for the first time. I like them, but I just could not figure out how to wear them to make them feel right and fashionable. Thank you!

      And I love that flare jeans are coming back too, since they are so flattering and so much easier to wear and pair with shoes ;)


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