How to Wear Ankle Boots

This post has now been updated for 2014! Click here to see it.


It’s time for the long-awaited next installment of “How to Wear”! This time I’m talking ankle boots or booties. They’re so darn adorable, but they can be hard to wear. They cut off your legs at the ankle (as you might have guessed), which can make you look shorter, which in turn can make you look fatter. I don’t mean to speak for all women, but I tend to shoot to look more like Gisele and less like Danny Devito. The key to wearing ankle boots is elongating your legs as much as you can while still showing off the shape of the shoe.

Your ankle boot styling options depend on the kind of heel you’re working with, so I’ve split my examples into 3 categories: wedges, flats, and heels.

Wedge ankle boots


Wedge boots are my favorite so I put them first! You get extra height, which makes them easier to wear, but they’re still comfortable. I wear my wedge ankle boots with cuffed skinny jeans all the time. Skinny jeans make my short legs look as long as they’ll ever look (still not that long). But cuffing them a bit helps show off the shoe. If you have cropped skinny jeans, that would work too.


Wedge ankle boots can work with a skirt or dress too, as long as the hem falls a few inches above the knee. The more leg that’s showing, the longer your legs look. Just keep it decent, OK ladies?

Shop Wedge Ankle Boots: Save // Spend // Splurge

Flat ankle boots


Flat ankle boots are the hardest. They accentuate my lack of height, but I still love them! I wear them with cuffed skinny jeans just like my wedges. You’ll notice in both of the above outfits I tucked in my shirt – if you’re already cutting off the leg line at the bottom, you don’t want to do it at the top too!


Friends don’t let friends wear leggings as pants. Always cover your junk. That said, leggings can be very slimming on your stems, and you can get away with a short tunic. Flat booties with leggings can be a fun alternative to sneakers or flip flops with a super casual outfit.

Shop Flat Ankle Boots: Save // Spend // Splurge

Heeled ankle boots


Heeled ankle boots can be worn almost any way you would wear regular old pumps. They’re a great option for the winter because they’re a little sturdier than pumps and you get more coverage on your chilly feet.

Shop Heeled Ankle Boots: Save // Spend // Splurge

See more How to Wear posts:

Army Jacket     Oxford Shirt     Denim Jacket     Flared Skirt

“Maybe I’ll Put on Pants Today”






20121020-231859.jpgWe took these pictures right after I got my hair done, which means this is the best my locks will look for the next eight weeks. Go ahead and enjoy it now. My stylist (and friend) reads my blog and she told me it’s inspired her to make an effort to dress better! Apparently to her this means simple things like putting on real pants, but hey…baby steps. (Brandy’s probably reading this right now thinking, “Dammit Sarah…next time I’m giving you blue highlights muahaha!”)

But seriously, I love it when people tell me I inspired them to try something new or to put on pants. It makes me feel very powerful. You are all my minions.

So minions, your tidbit for the day is on wearing flat ankle boots! I’m a fan of this style, but on shorties like me (I’m 5’3″ and proud), they can make legs look stumpy. It takes some experimenting. I read in a magazine recently that jeans should always cover the top of an ankle boot, but I personally think that looks a little funny sometimes. Plus, ankle boots are cute because they’re ankle boots, and how will anyone know they’re ankle boots if you cover the top? Anyway, I like cuffing skinny jeans right above the top of the boot. Just make sure your socks don’t clash because they’ll show when you sit down. If I still look a little stumpy, well…it’s because I am.

Top: Kohl’s (old, similar)

Jeans: Ann Taylor

Belt: Target

Boots: DV by Dolce Vita

Hello Again







Don’t you love it when you find something in your closet that you forgot you had? That’s what happened today with this necklace. It was hiding behind some big chunky things, poor little guy. I don’t even remember where I got it, but I like that it’s simple, yet still makes a statement. What kind of statement? I’m not exactly sure. Probably something like, “Hello. I am a necklace.” I don’t think jewelry is especially eloquent.

Anyway, about this little dress. As far as I can tell, it is a dress…which someone younger and with nicer legs might wear on its own. But I – being a professional student in my late twenties who hasn’t worked out in a while – always wear something under and/or over it.  In the summer, I’ve worn it with a crew neck t-shirt underneath, but for October this leggings and cardigan combo is working out quite nicely.

Dress: Zac Posen for Target (old)

Cardigan: LOFT (old, similar)

Boots: Nine West (old, similar)

Necklace: similar