How To Wear The Ankle Boot

Last week on my Tie It Together Thursday picture, I showed this picture with black ankle boots. Krista, who sent the picture of the dress, had mentioned wearing ankle boots with it in the fall.

Several of you asked about the ankle boots. How do you wear them? Do you wear tights, what color, etc.

How to Wear the ankle boot

I’m not sure I would wear boots with this dress. If I did wear ankle boots, I would wear black tights but I would have to try this on to make sure it looked right.

I decided to do some researching and thinking about how to wear the ankle boot. It looks like they’ll be popular again this fall/winter season.

Let remind you, just because it’s in style doesn’t mean we have to wear it. Not everyone looks good in ankle boots.

Here are some things to consider:

~~Ankle boots cut your legs off at the ankle so if you have short legs, it will make them look shorter.

~~Try to wear an ankle boot that is close to your skin color to avoid them cutting off your legs.

~~Ankle boots accentuate the ankle, so if you have large ankles, you may not want to wear them with a dress.

~~Ankle boots look great with skinny jeans.

I found some pictures with ankle boots that I liked. These are great examples of how to wear the ankle boot.

How To Wear The Ankle Boot


How To Wear The Ankle Boot


How To Wear The Ankle Boot


How To Wear The Ankle Boot


How To Wear The Ankle Boot


How To Wear The Ankle Boot


How To Wear The Ankle Boot


Now, here’s the question. Can women over 40 wear ankle boots? The answer is yes! We can wear them but make sure they look appropriate with the outfit you’re wearing.

I usually ask myself, “Does this look classy or trashy?” Of course if it’s trashy stay clear of it! :-)

So what do you think of the ankle boot? Do you wear them, do you like them? Let me know!

Beauty For the Heart~~I recently found a book of my Mom’s called HOPE, pure and simple by Max Lucado. It has so many good quotes and that’s what I’ve been using for my Beauty For the Heart. I hope you like them!

“God hasn’t given up on you. He hasn’t turned away. He believes in you.” -Max Lucado. I’m so thankful God hasn’t given up on me!! I’m still a work in progress.

Have a blessed day!

Share on Facebook3Google+0Pin on Pinterest0Tweet about this on Twitter0Email to someone


  1. says

    I’m kinda ready for this trend to pass. In the last two years, they’ve exploded. IMHO, neither ankle boots nor gladiator sandals are flattering on most legs. Women’s ankles are so pretty and covering them up seems to make legs look heavier than they are – even the thinnest of legs.

    Again, just my opinion…

  2. Judith Hall says

    I love ankle boots and I think the right pair with the right dress can look really great! In my opinion, I don’t care for the ankle boot/dress look on women over 40.
    Pants or jeans are an entirely different situation. I think any age group can look quite fashionable and well put together in ankle boots with jeans or pants. Cyndi, you make a great point we all need to remind ourselves of once and again, “just because something is in style doesn’t mean one has to wear it.” Words of fashion wisdom.

  3. says

    I too am thankful God has not given up on me! I would wear ankle boots with pants but at 63 I would not wear them with anything else. I don’t wear skinny jeans either but do wear a straight leg which on me is skinny enough :-) to wear with boots and look good.

  4. says

    Hi Cyndi.

    Yes! I am definitely a big fan of the ankle boot. I have a couple pair, and plan to add another pair or two this fall. Of all the looks/sources you show, the one with the cuffed jeans and cobalt sweater and coat is exactly how I usually wear them. If I’m not wearing a straight leg jean, I’ll wear them with skinny jeans. Stitch Fix sent me a pair of Kensie Ankle Bitter jeans, and I also wear them with those. One of my favorite fashion items is boots…all of them. :) I plan to try ankle boots with a LBD soon, so we’ll see how that goes.

    Hope you have an amazing week. Thanks for sharing the helpful hints.

  5. Kelly says

    I’m a fan of the ankle boots with skinny jeans. I MAY step out of my box and try them with same color tights this year. We’ll see how adventurous this 51yo Mimi can be:)

  6. says

    I discovered these last fall with skirts and dresses but prefer to wear them with tights the same color as the boot to accamodate my petite heigth.. This quickly became one of my favorite looks. Wearing them with skinny jeans rolled up is going to be big this year in my opinion.

  7. Krista says

    Thank you Cyndi for great information! I like the skinny jeans and brown/tan boots. I really like the cobalt skirt with the black tights and boots. Those boots don’t come up as high on the ankle and seem to give a longer line. This tutorial, however, has made my mind up completely… While I think this look is cute… It’s not for me! At only 5’2″ I will look like an elf!! My teen daughters are both taller than me and I think they will look adorable in this this look. I’m going to share your pictures with them. I have the pumps, handbag and bracelet you showed with my dress on order and I can’t wait for them to arrive! Should be this week:) I also love Max Lucado. Thank you again for your inspiring and fun blog! Blessings Krista

  8. Cindy D says

    I think they look cute with tights or pants…sadly, they don’t look right on I do love that jean jacket though-the one on the right (#1). I think that is on my list for fall!

  9. Liz says

    I have several pairs…love them! They look great with the textured tights too! I actually prefer ones with a heel rather than the flatter ones…that’s when you might be mistaken for an elf! I’m in my early 50’s and I think they allow me to be stylish and still classy and age appropriate!

  10. Rondell says

    I can’t wait to wear them with skinny pants and jeans, if a dress I’d go with black tights, ankle boots and black turtleneck sweater or top:) One slim look all the way up!

  11. Beth Ann says

    This is a great tutorial, nothing beats visuals to figure out how to wear this. I think I would try it with skinny jeans or tights in the same color as the boot. The ankle boot selection on Zappos is so cute, I especially love the ones from Clark and Born, as I imagine they would be comfortable.

  12. bobbi Griffith says

    I love them with pants and I love the pictures with the cobalt blue skirt and black tights I do not like them with short skirt without tights it reminds me of elves

Leave a Reply

Your email address will not be published. Required fields are marked *