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

Baby Boom





20121122-193557.jpgYou’re looking at me standing in the lobby of Union Hospital in Terre Haute, IN, where I went to visit two different friends who had babies this week! I got to see both moms and one baby (the other was in the NICU but is doing fine). I figured a great outfit was appropriate for the occasion since hospitals are pretty much the most fashion-starved places ever. Everyone’s in scrubs or hospital gowns. Normally, there are still regularly dressed people visiting, but the residents of Terre Haute are not exactly the best looking crowd (except for my friends, obviously). Actually, in Terre Haute, scrubs and hospital gowns might be an improvement over the norm.

Still, I’m happy to say that one little girl named Dylan got her first style lesson from me! (I also got her her first copy of Vogue, so she’s all set.) Congrats to all the parents! Better you than me!

Sweater: J. Crew Factory

Skirt: Anthropologie (on sale!)

Boots: Target (on sale!)

Bracelets: Forever 21 and Nordstrom

Tune in later today for the official announcement of the Gems & Jam Giveaway winner!

I’m Not Tired of You Yet





20121115-115042.jpgI hope you guys aren’t tired of seeing this boys’ polo, because I am so not done wearing it. I just love it. So comfy, great fit, and it’s striped! I’m a sucker for anything striped. Or with bows. Or leopard print. Or mint. OK, I’m just a sucker.

I wore this for a day at the mall, but don’t worry. The majority of the time was spent sitting at Starbucks working on a paper that’s due Sunday night (11 pages down, 9 to go). The rest of the time was spent doing a little Christmas shopping. Pretty soon I’ll be knee-deep in finals and I won’t be able to think about Christmas until it’s too late to get everything done. Oy. I know there’s a light at the end of the tunnel, but the tunnel is really freakin’ long and curvy so I can’t quite see it yet.

Shirt: J. Crew boys’ department (similar for grownups)

Sweater: Isaac Mizrahi for Target, old (similar)

Jeans: Seven

Boots: Target

Necklace: I.N.C. (similar, similar)

Watch: Anne Klein (similar)

Bracelet: Stephan & Co. via Nordstrom

Earrings: Kate Spade

A week from today, the winner of the Gems and Jam Giveaway will be announced. It could be you! But only if you enter, dummy. Do it here.

Comfy Cozy





I try not to walk out of the house looking like a box of free crayons from Applebee’s, but sometimes it just happens. I decided I’m OK with it, especially when it’s cute and cozy like this outfit.

I wore this Saturday to class and then to dinner with friends before I changed into my Halloween costume for the night (but you don’t get to see that until tomorrow).

On another note, I hope all of you on the east coast kept safe during the storm yesterday. Mother Nature is a moody bitch sometimes. If you know anyone who was in the path of Sandy, be sure to call and check on them! And if you’re feeling charitable, you can donate to the Red Cross here.

Turtleneck: Target, old

Puffer vest: Forever 21, old (similar)

Scarf: Target, old (similar)

Jeans: LOFT (similar)

Boots: Target

Watch: Anne Klein (similar)

Don’t Sweat It





20120924-203005.jpgHow excited am I about finding this polka dot sweatshirt? So excited that I’m erupting in random fits of laughter, as seen above. When you’re all cozied up in a sweatshirt but, at the same time, you’re managing to not look like an obese couch potato who buys generic Cheetos in bulk and eats them while watching the Maury show, it’s hard not to be a good mood. (Man, Cheetos sound really good now…Moving on…)

‘Twas a chilly but sunny fall day yesterday, the perfect excuse to wear a scarf and boots. It’s outfits like this that make me happy even in the midst of political ad season. And that’s saying something.

Happy sweatshirt available at Madewell

Jeans are 7 for All Mankind (similar)

Boots available at Target (run small)

Scarf from Charming Charlie (similar)

These Boots Were Made for Yellow






I’m happy to announce yet another successful fulfillment of my fall shopping list: wedge ankle boots. I originally had my eye (both of my eyes, actually) on the new TOMS boots, but I found these very similar ones at Target for less than half the price. Although, when you think about, with TOMS you’re actually buying two pairs of shoes, and you’re helping someone in need. However, I have several big-ish ticket items on the list, so I wanted to save where I could. Don’t worry, I’ll donate some money to charity around Christmas or something 😉

This is what I wore to class on Saturday (it’s been 4 weeks but “class” and “Saturday” still don’t sound like they should go together). The boots were super comfortable and I didn’t feel like I was wearing a heel, which is definitely important when I’m carrying around all the extra weight of books and a laptop. And can we talk about how the color looks so great with mustard yellow? Because it does.

Boots available at Target, also in black

Jeans available at LOFT in various colors

Shirt available at Forever 21