Look, I’m pretty sure I’ve made it very clear at this point that I love fall fashion, but this is the Internet, and there’s always something new to talk about. Today’s topic: Shoes. Who doesn’t love shoes? One of my favorite things about fall is that you’re not really restricted when it comes to footwear: It’s not so hot that you feel like your feet are sweating if you’re not wearing sandals, but you also don’t need to throw on the winter boots at the first sign of dropping temperatures. Perhaps the most perfect transition shoe is the ankle bootie. They have all the style of a classic fall closed-toe shoe with potential for exposed legs of summer—what’s not to love?
I can pretty much guarantee that you’ll be seeing ankle booties everywhere you turn this season, and that number of options can be pretty overwhelming. Quite frankly, I find it impossible to go into a great shoe sale at a major department store and have any success if I don’t have someone there with me for moral support. So, since you’re likely going to be attempting to take advantage of the Labor Day sales that extend way into the middle of the month, let me be your moral support! I’ve provided an example of different ankle booties of every heel height to help give you an idea of what you want. The best part? If you like what I’ve suggested, you don’t even need to leave your couch to buy them! I’m so nice, guys.
Check out some of my must-have ankle booties for fall:
ASOS Airbound Leather Chelsea Ankle Boots ($72, ASOS)
You’re probably familiar with this cut of the boot by now, as it’s taken the fashion world by storm this summer, but if you’re not, allow me to introduce you: This is what we like to call a Chelsea boot. You’ll be seeing a lot of boots claiming to be Chelsea boots in an effort to be on-trend, but the official definition of the term is “an elastic-sided, ankle-height boot,” of which this particular ASOS shoe is the epitome.
Cut-Out Ankle Boots ($195, & Other Stories)
This is for the girl who just isn’t ready to let go of her summer sandals. I know, letting go is hard, but this boot will act as a nice little gateway shoe into all the big, bad fall shoes that are waiting just around the river bend. Or corner. Honestly, I don’t know what type of environment you find yourself in.
Pointy Toe Ankle Boot ($79, Urban Outfitters)
I’m not normally one for Dr. Martens or anything like that, but I do appreciate a good lace-up boot, and I feel like the pointed toe on these gives them a more updated look as opposed to a grungy, military-esque one.
Franco Sarto Skylar Leather Booties ($129, Lord & Taylor)
This is the epitome of the fancy low-heel ankle bootie, and it’s all because of the gold zipper. And, well, because of the high-quality leather, too—these are Franco Sarto, after all. That’s another thing: There are a few lower-priced booties on here, and I’m all for bargain shopping, but please (PLEASE) try to invest in a good, sturdy pair, even if it is a little bit pricier than you’d like. You’re likely going to wear them out pretty quickly, and it’s easy and worth it to re-sole a bootie that you know you invested in than one that’s just a throwaway pair. Plus, I’ve been told that fake leather shoes start to smell after you wear them a lot, and while an odor-eliminating sneaker ball tends to help with that, there’s no reason to just try to avoid that occurrence altogether.
Rozamare ($99.95, Steve Madden)
Caramel-colored boots are probably my favorite neutral piece of all time. They seriously go with everything and have a way of making every outfit a good, chic, thought-out kind of casual.
Sam Edelman Jodie Chelsea Boot ($89.95, DSW)
I’ve had a deep, undying love for Sam Edelman ever since he put out a pair of spiked (and, quite frankly, probably weaponized) heels a few years back. Carrie Underwood wore them and looked like a total badass, and I could never get my hands on them because life isn’t fair sometimes.
Cutout-Heel Faux Leather Booties ($34.90, Forever 21)
Who said bootie detail had to come from zippers and studs? A metal cutout heel like this adds a ton of visual interest without over-accessorizing the boot. It’s subtle, yet still exciting and unique.
ASOS Radio Star Pointed Ankle Boots ($81, ASOS)
Hey, cobalt is one of the biggest color trends for fall, right? Instead of going for a sweater or bright nail polish (like I’m wearing right now, BTW), go for a pair of suede, cobalt booties. Like most suede products, they’ll require a lot of care (do NOT wear them when it’s raining out, you’ll regret the semi-permanent water stains immediately), but what’s a little upkeep in the name of a great shoe?
Vince Camuto Debra Bootie ($79.95, Nordstrom Rack)
This is about as simple as you can get, and I’m sure you’ve seen booties just like this at H&M. That said, Vince Camuto shoes really are little foot miracles—I got a pair for my birthday during my freshman year of college, and I’m still tromping around in them to this day.
Ecote Short Suede Boot ($79, Urban Outfitters)
Again, be careful with the suede, but the higher heel and simple design on these tan booties allow you the opportunity to dress them up a bit.
Cutout Faux Leather Booties ($32.90, Forever 21)
The chunky stacked heel may make it seem like these boots are lower than they actually are, but trust me, these are no laughing matter in terms of height. I can definitely see these working for the office or a date, and you can always pair them with tights if you’re worried about your feet getting cold.
Jessica Simpson Zerellah Bootie ($79.95, DSW)
I’m a sucker for a well-placed stud, and anyone who’s never tried on a pair of Jessica Simpson shoes is in for a very welcome surprise. Her shoes are universally comfortable and surprisingly long-lasting, and these are a good way to edge up an otherwise simple outfit.
Strap Ankle Boots ($195, & Other Stories)
Oxblood is always a good choice for fall, and I can guarantee you’re going to be seeing this color everywhere (after all, Pantone gave it their official seal of approval, though that was admittedly Marsala, not Oxblood).
Tried And Troubadour Bootie in Black ($69.99, ModCloth)
You’ve probably seen this kind of strappy (is that the right word to use?) design on a lot of booties over the years, but all the ones that I’ve seen lately have straps that are a different color from the base of the boot. While I don’t necessarily have a problem with that, I’m a big fan of more subtle detail, and this all-black pair is on point.
Lasso Heeled Bootie ($59.90, Express)
Okay, I’ll make an exception for these olive booties. They’re just so darn cute.
Sara Sheikh is a professional engineer and loves to design and embraces modesty in everyday life. She founded covered bliss in 2013.