Wardrobe Wednesday | How to Wear Ankle Booties

It’s right about now that I want to be in ankle booties daily, but being as short as I am, I didn’t think I could pull them off.  I’m happy to report I’ve sound several styles of ankle booties that are flattering on all heights, including us shorties! 😉
It’s true that booties can cut off the visual line of your leg, but if you style your booties in a flattering way, you can wear booties with so many things from jeans to dresses to shorts and pants.  Below I’m sharing five of my favorite pair of ankle booties and how to wear them, so you have lots of outfit options and ideas!
How to wear ankle booties - 5 bootie styles and 15 different outfit ideas

First up, the booties I know and love are (as seen from top to bottom in the picture above):
Vince Camuto Maves Bootie (on sale)
Sole Society Talisha Tassel Bootie (current fave, under $100)
Kristin Cavallari Laurel Peep Toe Bootie (nude color on sale)
Baila Ashton Wedge Ankle Bootie
Mine are old Vince Camuto, this is the new version Vince Camuto Saron Bootie

*On all of these booties, I order a 1/2 size up so I can fit at least a thin sock or a “no show” sock if I need to.

But, in case my booties are sold out or unavailable in your size, I found some similar, reasonably priced options below.


Suede Casual Booties


How to wear suede casual booties- lots of outfit ideas
A moderate ankle bootie such as the Vince Camuto Maves Bootie is a definite casual go-to.  The heel is about 2 inches, so high enough to give you some lift, but not so high that your feet are dying by the end of the day.  The heel is stable too, but not too chunky.  They come in red, green and black also, but the “beige suede” seems to go with everything (even black and grey)!
Vince Camuto Maves Bootie- perfect "go to" casual bootie for everyday with outfit ideas to go with them!
The key to almost any type of bootie is pant length or skirt style.  If you’re wearing jeans, you’ll most likely want to roll the cuff and a tiny bit of ankle showing is a good thing!  Of course, these are not hard and fast rules, and with a boot like this that has a wider leg opening, you can also tuck your pant leg, leggings, or jeans inside.
This first look is the boot with a military pant.  The olive green and tan are a great combo and because the pant is a skinny leg, it fits right into the opening of the boot.
Fall Fashion - military pants, tunic top, and suede booties
A dark skinny jean and loose fitting cardigan over a tank or fitted top is an easy outfit for Fall.  You can roll your jeans in a “messy” sort of way, so they don’t look too perfect at the bottom.  It’s a casual vibe you’re going for here.


Fall fashion - dark skinny jeans, cardigan sweater, and suede booties
Don’t forget that you absolutely CAN wear your ankle booties with a dress and with or without tights.  This dress is a flannelish plaid, so the heavier fabrics work well together and the colors go great together.
Fall fashion - love mixing a plaid shirtdress with a low bootie

Tassel Booties

I must say I’m super loving these tassel booties at the moment.  Mine are the “taupe suede” and they are the cutest with the little side tassel.  The wooden heel is a bit higher (3 1/2 inch), but perfect for adding extra height and lengthening the look of your leg.  And since the front of the bootie dips down, it’s also a leg-lengthening cute.  Because the heel opening is slimmer, I definitely like to show a little ankle above the bootie, like in the photos below.
Sole Society Talisha Tassel Bootie- so cute! & outfit ideas to go with them!
To achieve this rolled jean cuff, I actually fold the jeans underneath, then flip outward so just the bottom hem is showing. Of course, this is because my jeans are actually long enough to do this on.  You’ll need a little extra jean length to achieve the rolled cuff look.
Fall fashion - super cute kissing fox sweater with rolled jeans and tassel bootie


Fall fashion - the colors in that scarf! and under $25! with a tassel bootie!


Fall fashion - rolled jeans, wrap cardigan and tassel booties - easy weekend outfit

Black Booties (Wedge and Heeled)

Black Heeled Ankle Booties

With these super low ankle booties, I either forgo socks or wear a thin, “no show” sock that won’t show above the shoe.  This pair (3 for $16) comes in black, tan or white and has loads of positive reviews.
Mine are old Vince Camuto, this is the new version Vince Camuto Saron Bootie
A cigarette pant in black is slimming with these types of booties and you can layer on top a button down and sweater for more visual interest.
or you can wear your bootcut jeans over them.
Fall fashion - bootcut jeans with heeled booties
Fall fashion - black heeled booties with jeans- her blog shows lots of options for how to wear your booties
skinny jeans | red top | Rocksbox necklace – get 1st month free with code HONEYWEREHOMEXOXO
old tee from Loft | leopard skinny belt

Black Wedge Booties

These wedge booties are awesome!  I love the style and fit and they can be dressed up or dressed down, depending on your mood and the look you want to achieve.
Baila Ashton Wedge Ankle Bootie- awesome! & outfit ideas to go with them!
I like these wedges with a skirt and opaque tight for a casual dressed-up look, and adding a denim jacket adds to the casual factor.
Fall fashion - great way to wear skirt with wedge booties & lots of other bootie outfits on her blog too
black skirt (similar)  | black opaque tights | jean jacket (similar) | striped sweater (similar) | necklace
Cutoff jean shorts and a button-down top is also an easy weekend look when you’re transitioning between the seasons.
Fall fashion - button down shirt + cutoff jean shorts + booties, great for transitioning from summer to fall
jean shorts | Old Navy button down (similar)
Peep Toe Booties
These peep toe booties were a “had to have” moment and I’m so glad I bought them.  These shoes look awesome with jeans or dresses.  The peep toe nature of the boot adds a little sexiness to the look, but don’t forget to paint those toes!
Kristin Cavallari Laurel Peep Toe Bootie - love these! & outfit ideas to go with them!
Fall fashion - perfect for transitioning from summer with a tunic top, distressed jeans and booties
Fall fashion - love pairing a shirtdress with peep toe booties!
Fall fashion - love this racerback dress with peep toe booties and super cute Kendra Scott necklace
Racerback Shift Dress (under $50 and 8 colors) | Kendra Scott necklace | clutch

:: shop the looks ::



How to wear ankle booties - 5 bootie styles and 15 different outfit ideas


Which ankle booties are your favorite? 
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Meet Megan

Hi! I’m Megan, mom to a thoughtful teenager and spunky young girl. We call Houston home and recently moved into our dream home. I traded my lawyer hat to become a full-time blogger in 2010. I love sharing my passion for affordable fashion, home decor, organization, & fitness to help inspire you to take care of you!


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