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

Boot Love



You’re looking at a class photo of my boot collection. I didn’t realize I had 16 pairs until I started pulling out all my winter clothes! I think it’s safe to say I am boot-obsessed. Some of these you’ve already seen in action multiple times, and some are still waiting to make their blog debut. But in the meantime, I’ve channelled my love of boots into something worthwhile: finding some bee-yoo-tiful boots for your viewing and/or shopping enjoyment. Tell me your favorites in the comments!
Tall Boots
1.  Express, $79.90 // 2.  Alfani, $99.99 // 3.  LC Lauren Conrad, $64.99
4.  Gomax, $59.99 // 5.  Yves Saint Laurent  (you don’t want to know how much)
Dressy Boots
1.  LAUREN Ralph Lauren, $97.99 // 2.  Steven by Steve Madden, $179.00
3.  Dolce Vita, $179.00 // 4.  Laurence Dacade, $455
Flat & Wedge Booties
1.  Rampage, $39.95 // 2.  MIA, $88.50 // 3.  DV Dolce Vita, $99
4.  Plenty by Tracy Reese, $165 // 5.  Juicy Couture, $250

Old and New






Kristin’s last performance of Rocky Horror was yesterday, so I went to see her in all her raunchy glory one more time. (In case you missed it, here‘s a peek at her costume.) I was a bit overdressed (story of my life) for a Sunday matinee, but I just bought this dress and I was desperate for an excuse to wear it.

Sometimes when I wear something new for the first time, I like to pair it with something old that I haven’t worn in awhile. Maybe I subconsciously feel guilty for neglecting my old clothes in favor of the new ones. It’s kind of like when parents have a second child, and they just let the first one play in traffic and eat cigarette butts. That behavior is generally frowned upon, and so too should ignoring old but cute purple ankle boots like these.

I hope everyone has a great week! In case you were wondering, my week will be spent in sunny Florida! Yep, as you are reading this, I might be flying over you. For the next few days, you can look forward to some vacation photos, including a historic event: my very first visit to Disney World. Stay tuned!

Dress: Target

Coat: J. Crew

Tights: old (similar)

Boots: old (similar)