How to Wear Ankle Boots for Fall
Ankle boots and fall go together like peanut butter and jelly – they’re a perfect combination. That begs the question: what’s the best way to wear a pair of these fall booties? The short answer? There is no best way. Ankle boots are incredibly versatile so you can wear them with basically anything: jeans, skirts, tailored pants, dresses – you name it; it all depends on your personal style and what you’re most comfortable in.
And with that out of the way, let’s look at some of the ways you can style your favorite ankle boots for any occasion on your calendar!
Types of Ankle Boots for Women
Before we get into HOW to wear them, let’s talk about some of the different types of ankle boots for women that exist:
The Flat Ankle Boot
Think of these as your everyday, wear-everywhere staple. Like their name suggests, they lack any kind of lifted heel which them the ideal shoe for the women on-the-go. They’re comfortable, stylish, and oh-so-versatile – you can wear them with everything from jeans to dresses. Since they do lack a heel, most people don’t feel they’re dressy enough to wear to formal or professional events so they’re definitely a style you’d wear with more casual looks. Style-wise these are often a Chelsea boot or even a combat boot (or both).
The High Heeled Ankle Boot
If flat ankle boots are your everyday staple, then these would be your statement-makers. Weddings, galas, date nights – if you’re trying to make a lasting impression, these ankle boots are your best friend. Typically characterized by a high, slim heel these are boots that mean business. These usually come if a few different styles, from your neutral black ankle boots that are more business focused to rhinestone encrusted boots that really bring that “wow” factor.
The Block Heel Ankle Boot
Also known as chunky heel boots, this iteration of ankle boots gives you a more lift than a pair of flats would but more support than high-heeled ankle boots (so, basically, the best of both worlds). These are the styles that put the fun in function – their block heel is comfortable enough to wear all day, while their heel helps give them a more elevated (literally) feel that’s perfect for more formal or professional occasions. Style-wise you have a ton of options with these women's boots: you can channel your inner cowgirl with a pair of Western boots, give your look a little edge with a pair of moto boots, or stick with the tried-and-true a little black booties.
How to Style Ankle Boots
How to Wear Ankle Boots with Jeans
Jeans are a fall staple and, let’s be honest, are what you’re probably going to spend most of your time in this season (and for good reason; jeans are comfortable, stylish, and oh-so versatile). But that is also why you need to put a little extra thought into how you’re going to style your fall booties while wearing a pair of jeans.
First thing to think about? Wearing the right ankle boot for the right occasion. You’re probably not going to wear the same pair of boots pumpkin picking that you would to a girls’ night out, so you need to be mindful of that. Then you also have to consider how your jeans sit at the bottom – jeans with a longer inseam require you to wear a lower ankle boot, whereas cropped jeans or pairs with shorter inseams you can really showcase the details of higher ankle styles and make them the focal point of your outfit.
Pro-tip: if your jeans are too long for your favorite pair of ankle boots, try rolling or cuffing your jeans. That way you can still rock your favorite pair of denim AND show off that new pair of Western boots you just picked up.
How to Wear Ankle Boots with Skirts and Dresses
The good news: you’ve got options! The bad news: you’ve got options.
With dresses and skirts, you’re usually showing a fair amount of bare leg, which means you can wear literally any pair of ankle boots in your closet and not worry about your outfit hiding them. But that blessing is also a curse because it draws more focus to your footwear – if something doesn’t fit as well and doesn’t really match the rest of your outfit people are going to notice. So, your main goal when shopping for a pair of fall booties to wear with your favorite dress of skirt is this: you want something that both flatters and works with your legs natural shape.
After that, you just need to decide what you’re trying to do with your boot: do you want something that works with your outfit, or something that is your outfit. For the former, you probably want to keep your ankle boots simple – maybe a simple black ankle boots or neutral bootie that won’t draw too much attention away from the rest of your outfit. If you’re looking for the latter, have fun with it! Maybe wear something you wouldn’t typically, like a blinged out western boot or a Chelsea boot with intricate detailed work.
How to Wear Ankle Boots with Trousers
Typically, if you’re wearing ankle boots with trousers it’s going to be for a more formal or professional type of event, which means you’re going to want to go with something that has a little more height to it like a high heeled boot or a block heel. For professional events it’s all about posturing – a neutral heeled boot will give a little added height that helps you standout, whereas a more vibrant, standout boot can help give your look a little bit of an edge and channel that boss-girl energy.
For formal events you can have a little more fun with it. Trying to keep it simple? A little black bootie still gives you that formal look without drawing too much attention or taking away from the rest of your outfit. Want to make a statement? Break out the rhinestone Chelsea boots or the frilled Westerns.
How to Wear Ankle Boots with High Socks
There’s nothing wrong with wearing your ankle boots with no show socks. It’s a classic, tried-and-true style that works. But, if you want to have a little more fun with your look, give the stacked sock look a try. Basically, it just means wearing higher crew, ankle, or knee socks and then scrunching them down so they’re resting just above the top of your boot.
Now there’s a few different ways to rock this trend, but our personal favorite is to pair an edgier ankle boot, like a combat or moto, with a classic pair of white tube socks – the contrast really helps your boots to shine.
Ankle Boots for Women at DSW
Now that you know how to wear them all you need to do is find your perfect pair, or two, or three (and if you need a little help you can check out our Boot Buying Guide). Whether you’re looking for a pair of black ankle boots, Western boots, Chelsea boots, or any other pair of fall booties there’s only one name you need to remember: Designer Shoe Warehouse. DSW is your one-stop-boot-shop for all your fall bootie needs. Oh, and if you need wide-width or wide-calf boot styles, you can find those here, too!