Fall Trend: Ankle Booties (And How To Wear Them)



Mamas!  The easiest way to give your old standbys a modern spin?  Yup – the ankle bootie.  These guys aren’t new…in fact, two years ago, a very pregnant me wrote an article called The Short Boot Dilemma…where I tried to figure out how the heck to wear the various short boots that were popping up.

Well.  Two years later, I’m happy to say that I’ve figured it out.  Feel free to applaud.  Two years in the making, baby.  TWO.

Ok.  Here’s what’s working for me:

Leggings & Tights

This is a no brainer.  Ankle boots look awesome with leggings and tights…AND…the fabric protects your skin from any ankle-boot rubbing.  Best of all?  Leggings and tights are, well, tight enough so there’s no unsightly bunching about the boot.  So yeah.  Easy.   Want a pic?  I wore ankle booties with layered tights here, or with a pretty dress and sheer stockings here.

With Bare Legs

Ankle boots are super cute with bare legs…if you can stand it.  Some of my ankle booties are comfortable enough without socks (these and these), however my newest purchase…IS NOT.  These DV boots are cute, but rub the heck out of my bare skin.  To the rescue?  Cute, patterned socks!  Slightly scrunched.


(wearing: chambray shirt – Anthropologie, sold out here’s similar, shorts – old Gap maternity jeans hacked off, socks – Target, belt – Coach, clutch – Madewell, sunnies – Salt, booties – Java booties DV by Dolce Vita)


I’ve seen some gals rocking a colorful sock with ankle boots…and they totally pull it off.  I’m a bit shorter, and prefer to have my socks blend in (a little bit) with my ankle booties.


With Pants

This is where ankle boots stumped me two years ago.  It seemed as though most of my pants were going to cover the ankle boot totally….or bunch out at the top.  I hate the bunching (makes me look short) and covering up my ankle boots defeated the point.

That said….I’ve found that I’m OK with a little bit of bunching…as long at the skinny pant is tight enough at the ankle.


(wearing: pants – Zara, Java booties – DV by Dolce Vita, Farm Rucksack – Makr, moto jacket – Roots, scarf – Banana Republic)


But for pants like these….the bunching drives me nuts.

As does my hair

(wearing: shirt – Old Navy last season, sweatshirt – Forever 21 old, denim – Abercrombie and Fitch mid-rise super skinny in medium destroyed wash, Java booties – DV by Dolce Vita)


The solution I like (which for some reason didn’t dawn on me two years ago), is to roll my pants!  There are a million ways to roll.  You can do a small roll (turned up 2-3 times)…


I like the small roll with most jean types – from skinny jeans (that are just a little bunchy), to straight leg, to boyfriend jeans.  Or, for something different, try a really wide roll, turned up once or twice:


(wearing: turtleneck – American Apparel and currently on sale for $7, denim – Current/Elliott Slouchy Skinny here’s a similar pair, belt – Coach, Java booties – DV by Dolce Vita, bag – vintage aka my Mom’s)


The other option (especially for dark-wash denim) is to hem them to the very top of the ankle bootie.  This is a really flattering length, a sort of Audrey Hepburnish vibe with flats, a London-rocker with ankle boots.  Looks great with heels, too.


(wearing: pants – AG patched denim,  chambray shirt – Anthropologie, sold out here’s similar, sweater – old from Urban Outfitters, Java booties – DV by Dolce Vita, sunnies – Salt)


What About Socks??

With all of this pant-rolling, at some point, your socks are going to show.  Especially as we’re bending down, picking up the kiddos, crawling around with Hot Wheels, etc etc etc.  You can always do the guy thing, and match your socks to either your pant leg or you boots.  Or….a fun little pattern?


 (wearing:  target socks)

But…I gotta be honest, Mamas.  As much as I like how my little fancy socks look…most days I’m still reaching for my thick Smartwools.  IknowIknowIknow.



See those blue woollies peeking out?  I LOVE them.  This might be a fashion faux-pas, I don’t know.  But whatever.  There are just some things I can’t compromise on.  And thick, woolly socks is one of them.  Are two of them? (Grammar queens, help me out here).

But tell me Mamas…are you thinking of rocking ankle boots this year?  Mine have a small heel, but are still comfortable enough for toddler-chasing…even up the rocks in Central Park (we just did a quick little visit).


I know I’ve seen some fabulous ankle boots that are flat, yet wildly cool.  I pinned a bunch of my favorites to our Coolest Mom-Friendly Shoes board.  Thoughts, Mamas?  Have you found a pair, or are you sticking with just tall boots this Fall?




  1. Hello. I am obsessed with ankle booties and have bought several pairs for this season and appreciate your suggestions. However, I am a working Mama and have to dress the part most days. Do you have any suggestions on how to wear these correctly with dresses, work pants and maybe even a skirt suit? I live in Atlanta so it’s milder here and I’ll wear dresses without tights for most of Fall. Thanks for your help.

  2. Ahhh you look fabulous! I wish I could pull these looks off 🙁 I don’t know what I’m doing wrong but when I pair my ankle booties with my skinny jeans/pants, it just doesn’t look right. I can only wear them under bootcut jeans.

  3. omg, I have been seeing those DV booties all over the blogosphere lately, and coveting. COVETING, I tell you. But I just splurged on this pair of Clarks (linked below), and don’t think there’s another pair of boots in my wardrobe budget (I’m like a bazillion months preggo and am going to need a few key postpartum items)…. hmm, should I return the Clarks? I have no other tall boot, but I do have a wedge bootie I bought last season (see here:http://youfrillme.tumblr.com/post/16351576400/hot-pink-blazer )… comments, gals?

  4. How tall can boots be to qualify as ankle boots? I have a pair that go up to low shin and I’m not sure if these suggestions would work?

  5. I’m nervous to go with tights, because I’m afraid my post-baby body can’t possibly be flattered by them…but I love the look. I definitely want to pick up some ankle boots; I am kind of tired of my tall ones, and I hope I don’t look old-fashioned wearing them!

  6. Freebird by Steven has some great ones out now, and they’re not as heavy as Frye, which is such a relief while running around all day. I bought a pair and love them.
    I have gone with the technique of rolling my pants to avoid the bunching.

  7. Great ankle bootie review! I just got this awesome Born ankle booties (Roslyn). Super comfy and great for running around chasing two toddlers and dressy enough for work. I wear them with sheath dresses, pencil skirts, and pants.

  8. Girls – got mine at Old Navy of all places. Not the wedge ones, the vaguely western ones. And, I have been wearing them straight out of the box, no socks, nada. They have a two inch heel, and I’m not a heel person AT ALL, but these things are super comfy, and super affordable. Word.

  9. The day before reading this post I saw a young woman walking (while I was driving, so no picture). She was wearing a shirt dress, messenger bag, dark brown ankle boots and white, rolled/scrunched socks. It was pretty cute. I might have been staring. Which makes me a bad driver…

  10. @ Liz Law Mama – LOVE those things. Good choice!! (You could rock them now, BTW, with shorts and no socks…)
    @Sara – I’d pair dark, heeled ankle booties with a skirt suit. It’s totally work-appropriate…just gives it a slight edge, which I love. I wear mine with a pencil skirt (and bare legs in the summer) or with tights in the winter. I don’t know if you can do cropped trousers, but ankle boots would look great with a cropped trouser. Something like my Lands End outfit here, but with heeled ankle booties: http://www.aintnomomjeans.com/2012/08/pardon-me-but-do-you-chino.html
    @Miranda – Those are HOT!!
    @Beth – I think so…if your calves are muscular, I’d look for a pair of ankle booties that have a very low rise. And then be sure to show some slim ankle peeking out between the pant leg and the boots.
    @Claudia – Send me a pic. I’d love to help.
    @Fran – AUGH. This is a toughie. Your new Clarks are pretty fabulous (I just pinned them). And you already have a wedge bootie and you are preggo….what’s the weather where you are? If there’s any chance of muck or snow, I’d stick with the Clarks. As much as I love my ankle booties, once winter comes, they are pretty much moved to the back of my closet.
    @Jennifer – It depends on how wide the boot is. I have some mid-shaft boots that I can slip under straight-leg jeans, as long as I do the big cuff I’m showing above (a larger size roll, but rolled fewer times). They also work with boyfriend jeans. However, one of my friends has mid-shaft Fryes that are pretty wide…but could roll bootcut jeans over them. It actually looks pretty good with bootcut – makes them more of a boyfriend jean.
    OK Mamas – I’ve gotta go relieve the sitter. More later. Thanks for the comments!!!! It’s so fun! xoxo

  11. Oh S… ankle boots aside (which you totally rocked and inspired) but THOSE CAMO PANTS!!! I just didn’t think my girl crush could get any bigger, but alas!!!

  12. I agree with Tysie. I am completely obsessed with those camo pants and just snagged a pair. Please feel free to wear them in every post from now on so I get more ideas on how to style them. 🙂

  13. Ok – trying to catch up:
    @Lyn – send me a pic! I’d love to help!
    @Lauren – I think tall boots are a classic. There’s nothing old fashioned about them. Just classic. But that said, I know I’m appreciating the tall-boot break! And tights should be OK with any shape…just find a dress you LOVE. (And I’ve been impressed with Old Navy’s lately…crazy, I know.)
    @Jen – great pick!
    @Gretchen – HOLY CRAP. My new favs. Seriously. I have no words. Just pinned.
    @Boston Mama – thanks for the pick! Love the side detail.
    @Megan – Word to the Old Navy find. Nice.
    @Ashley – AWESOME drive-by sighting! Thanks for sharing.
    @Olivia – I’ve seen all shapes and sizes rocking the ankle boot. The key is finding a pair you feel good in. And when in doubt? Go monchrome. Makes anyone look taller. 🙂
    @Shannon – Yes. Abso-freaking-lutely.
    @Maggie – I love those boots! However, the heel height worries me. I wouldn’t be able to use them most days…..
    @Tysie – Your comments always make my day. 🙂
    @Meg – Ah…yes. You’ll have to hold me back, actually. They are literally ALL I’ve been wearing.
    @Sarah – Awwww….thanks, Chick!

  14. Booties aside, I am super in love with the camo pants. So, I asked my husband if he thinks I can pull them off. I got a look, a near eye-roll and “ugh, no”. Ouch, right?

  15. What about all those cute Zara ankle boots? They all are cute and have the added benefit of being pretty affordable. I like the Flat Chelsea Boot. What’s your favorite, if any ?
    Thanks for your great blog!!! Love your clever descriptions with matching pics!

Leave a Reply