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?