Choosing the Right Pair of Ankle Boots

In the Style Help Survey a bunch of people asked questions about ankle boots.  How do you wear them?  Is there a trick to making them look good with jeans?  What are some outfit ideas with skirts and dresses?  How can you make them appropriate for work or conservative settings?  And the list goes on.

The honest answer is that in many ways they still perplex me too.  But, I’ve tried a million different pairs and feel like I’ve learned a few things from trial and error.  Maybe other ankle boot savvy readers can fill in some blanks, too.

I’m breaking this up into multiple posts.  Today we’ll discuss different ankle boot options as they pertain to a) different cuts and heights, and b) different styles and how they affect your overall look.  Just the basics.

Cut of the Boot
I’ve found that the cut of the boot makes the most difference in whether or not I think I can pull off ankle boots or whether they make me think, “I guess I’m just not an ankle boot person!”  Some boots make my legs look stumpy while others don’t because of how they are cut.

Of course, this is up to preference.  Some people don’t care about legs appearing longer or shorter or leaner or not, and that is totally fine.  In fact, it’s more than fine–it’s awesome.  It’s probably even better because you can freely wear whatever pairs you want without stress or worry!  Unfortunately, I’m not that kind of person and I am conscious of my legs looking stumpy.

For me, it’s all about where the boots hit in relation to my ankles.  The confusing part is that while some look more okay than others with dresses, that same pair of boots could look terrible with jeans and vice versa.  We’ll talk about wearing ankle boots with jeans and dresses/skirts next time, but for now these are just examples of different boot heights.

Top Row – Flat
1.  Low ankle.  Hits the middle of my ankle bone.
2.  Slightly higher low ankle.  Hits the very top of my ankle bone.  This pair is also kind of higher on the outside than the inside.  No idea why, but that’s what it is.
3.  Slightly higher than #2, just high enough to cover my ankle bone completely.

Flat boots are very hard for me because most of them cut off my legs.  Of these, #1 is my favorite because I think it elongates my leg the most.  (However, I think I am returning them due to the color not being what I want.  Sad!)  The second one is alright, and I don’t mind it so much, but I still prefer #1.  The third is my least favorite, even though I’ve totally worn this boot with dresses before.  Because of where it hits my ankles and with my ankles being narrow and having more curve to my calves, the looseness around the ankle kind of makes me feel like I’m wearing elf shoes.  Haha!  Maybe I’m nitpicking, but #3 looks too clunky and sloppy to me, especially compared to #1.

Bottom Row – Heeled
4.  Cut out in front.
5.  About an inch above my ankle.
6.  A few inches above my ankle.

Heeled boots instantly look better than almost all flat boots on me because the heel naturally elongates your leg which gives you more wiggle room with how high the top of the boot is.

Pair #4 is my very favorite pair of ankle boots.  It has a little cutout in the front which allows more of your leg to show.  It was this pair of boots that, once I found them, gave me a little hope that I could pull off ankle boots.  (They’re from Target a few years ago, but there’s a similar version on 4 colors HERE.)  These are also the easiest for me to wear with jeans because they automatically show a peek of skin without having to roll your jeans much.  (We talk about that HERE.)  I also really like that the top of the boot hugs my ankles because I feel like it helps balance out the curve of my calves, similar to how wearing straight legged jeans helps balance out and streamline curvier hips.

Pair #5 hits about where #4 does, except there’s no cutout.  If my skirts are above the knee, I feel okaaaay about these, especially because the part around the ankle is fitted.  Pair #6 lands a couple of inches above my ankles and feels too bulky for my taste.  While I did show this pair with my striped Old Navy purple swing dress recently, I didn’t particularly like how much they cut off my legs.  I was trying to ignore it and be the kind of person I talked about earlier and not care.  But like I said–I’m not that person, and I care!

Which type flatters YOU is entirely dependent on your body and how it mixes with a particular boot you’re trying.  And for some lucky people out there, everything will be flattering on you.  The point was simply to illustrate that not all boots are cut the same, and just because one type doesn’t look good on you doesn’t mean all ankle boots won’t work for you.  Keep trying different cuts!  There are so many that you’re bound to find one that looks good on you.

All in all, as you can hear in everything I said, I can get pretty picky about ankle boots.  But you don’t have to stress as much about it!  I’d just recommend avoiding the looks in the last column as the clunkiness seems a little awkward and not as polished.  

Style of the Boot

After nailing which cuts work for you, then you can hone in on styles.  When I talk about “style” I’m referring to things like how many buckles it has, whether or not it has a zipper, how pointed or rounded the toe is, the type of heel, whether it’s suede (like this array HERE) or leather, if it has fringe, bells, and whistles or whatever.  You know, all the kind of stuff that gives the boot character.

Below are a bunch of different styles.  I feel like I only scratched the surface of them, as it can kind of be overwhelming!

About 1/3 of these are budget-friendly from Target while the rest are from Nordstrom, 6pm, etc.  Also, many of them come in different colors!

Links to Shop:
one  |  two  |  three
four  |  five  |  six
seven  |  eight  |  nine
ten  |  eleven  |  twelve

Some work better in a professional setting than others.  The second to last row shows pairs you can wear with slacks or pencil skirts if you need to up the professionalism even more.  
I gravitate more towards classic styles like in Row 1.  Though I wouldn’t mind fringe, like Row 2.  I tried the wedge bootie (number 12) in store and it seemed really comfortable.  I’m also leaning towards a peep toe bootie like the ones in the last row for this fall.  

Anyway, it’s just a visual for more ideas of different ankle boot styles!

Soon to Come
Later we’ll talk about tips for how to make them work with jeans, dresses, and skirts.  After that I’ll put together some outfits with ankle boots.  Stay tuned!  *Edit: That post is now live HERE.  

As I write the next post, do you have anymore questions on ankle boots?

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