The Four Ankle Boots You Need For Fall

For me, boots are a lifestyle choice. If you see me out and about on any mildly cool day, chances are, I’ll be rocking a pair of boots. Hell, I even wear boots in the summer. I find that the right boot can instantly elevate any look. This is a trick I employ quite often, as evidenced by the kind homeless man I often greet on my way into work. He doesn’t know my name, he simply calls me, “Boots.”

Regardless of if you wear enough boots to justify adopting their namesake as a moniker or you’re new to ankle-covering footwear, you probably need a new pair for fall. (And if you don’t need some, you want some, and it’s a justifiable purchase, since boots are always necessary.) I’ve been working on slimming my wardrobe and recognized a pattern in my footwear—particularly my ankle boots—so, take it from a pro: these are the four kinds of ankle boots you should probably add to your autumn rotation.

“o1.
Everyday”

Even for those of us who try to change up our look on a fairly regular basis, there are those priceless pieces we can’t help but wear time and time again. For me, it’s my beloved Helmut Lang pointed ankle boots. Leathery butter, timeless shape, and oh so versatile. That versatility is the key when it comes to finding your ideal everyday ankle boot. Though I’ve been known to splurge every so often, I follow a rule when it comes to shoes and bags: it’s called the $1 rule.

Think of it this way: if you paid $1 per wear, would it add up to the cost of that piece you’ve been coveting? $200, $300, or even $400 for a pair of shoes is a lot of money, but if the style and quality can stand the test of time, the price may be worth it, especially when you consider that some less-expensive options may not last as long, and $50 boots once every few seasons could add up to just as much. I made that mistake, which is why when I found these babies, I made them mine. They were exactly the size and shape I’d been looking for—for years!—so I knew I wouldn’t get tired of them. They’re simple enough to not only last a while, but also to wear every day. I wanted to check out my $1 rule in action so I’ve actually been tracking how many times I’ve worn them since I got them in the middle of the summer: it’s been over 50 times! That’s a pair of Zara boots right there—plus I got these secondhand. Kinder to the environment and my wallet. Win, win, win.

When you’re shopping for your everyday boots, keep these practices in mind. If you wear mostly black accessories like I do, stick to black. If you wear brown, go with that. Take a look at your wardrobe and think, “what could I wear to work, hanging out, and running errands?” I went with a slight heel so they’re sleek, chic, and grown-up, but also practical for running up the stairs of the El to catch my train. I also love what a pointed heel does to my legs, (makes them look super long) and the height of these is perfect for jeans and dresses alike.

Alternately, I wear my sock booties a LOT. I bought them on a whim to go with an outfit I had for a special occasion but found myself pairing them with things like jeans and skirts when I wanted some more “trendy” but still practical vibes. They’re generally more affordable and a good vegan option. I’ve linked a few options of these, as well as some of my picks for leather booties.

“02.
Statement”

I’ve never gotten as many compliments on a pair of shoes as I have on these woven ankle boots. They’re unique for sure, and with the right outfit, they certainly steal the show. I like having a few options for statement booties because they can make an otherwise kinda boring outfit into something absolutely Instagram-worthy. Picture this: black jeans, black top, black hat… and a killer pair of faux snakeskin boots.

Things to keep in mind when selecting your statement booties? Keep it interesting, but neutral for your wardrobe. (Black and white, grey, browns, even a subtle floral pattern.) There’s nothing wrong with bold patterns but remember: we’re going for wearability over and over again.

“03.
Elegant”

Elegance is not something that comes easily to me but I do adore the few pieces I have that are dainty and polished. One such example of this would be these darling pointed (surprise) ankle boots with teensy tiny peal details. They’re made of tulle, so I don’t think they look out of place with a cocktail dress or silky jumpsuit for a cold weather wedding.

Pro tip: an elegant bootie is a good thing to look for at the end of the season. They’re not as popular of a sell because they aren’t as versatile, and you won’t wear them as much so… see what I’m getting at here? I bought these on sale, because I don’t wear them as much: just special occasions and when an outfit needs that extra little touch.

For my elegant boot option, I went with black with some nice details but metallic or satin would be good options as well. Maybe look for something with some special added embellishment, such as jewels, pearls, or embroidery.

“04.
Casual”

Last but not least… the casual boot. These are ones that are best for running errands and going out with friends. Some offices may not be Doc Marten friendly, which is a damn shame but, rules are rules, I suppose. I have a small collection of Docs that I rotate in and out, but I also have a well-loved pair of Steve Madden boots leftover from my barista days. They’re kind of covered in milk and coffee stains but I think they’re the perfect shape and they’re wonderfully broken in so I keep wearing them. They look good with simple, flowing dresses, skinny jeans, and even joggers.

They key to a good casual boot is making sure it’s COMFORTABLE. (So yes, Uggs definitely count.)

What do you think? I think it might be time for you to treat yourself to new boots.

xo, e.m.