How to Style Your Contemporary Ankle Boots

How to Style Your Contemporary Ankle Boots

Every year when the leaves start to turn, the ankle boots come out. Can you blame everyone for loving this style year after year? A great pair of ankle boots simply works brilliantly as a tonal and textural contrast to your favorite pair of skinny jeans with a chunky sweater or coat. It’s an ideal recipe for Fall style and coziness.

But let’s be honest, sometimes you spot some fantastic suede boots that have been ruined by some loose jeans or other style mishaps. The best ankle boot style might look effortless, but there’s actually some key details you need to get right. So we’re here to break down which ankle boots you should be looking at this season and how to style them.

The best ankle boots this season

Of course “ankle boots” encompasses a wide variety of shoes, so let’s start by breaking down your best options for this season and which might be best for you.

The high heels

One of the downsides of ankle boots is that they can be harder to pull off for shorter women. That’s where a pump heel can make a big difference. By creating a longer leg silhouette (the kind that tends to make ankle boots look their best) and sticking with a thicker heel, these ankle boots let you stay comfortable and practical.

The Oxford ankle boots

Plain suede and leather ankle boots are classics at this point, but the Oxford ankle boot makes a strong case that it belongs in that camp as well. With a nod to classic collegiate mens wear and subtle leather details that can balance out an outfit, these boots do a lot of work.

The chunky flat ankle boots

Chunky boots and shoes are still going strong and they’re leaving a major mark here as well. From combat boots to more classy chelsea boots, thick chunky heels can provide a nice anchor to an outfit and contrast well with thin lines created by something like a pair of skinny jeans. Plus, they’re great for rough winter weather and there’s just no denying it: they make you feel like you can take on the world.

How to style your ankle boots

Once you’ve found the perfect pair of ankle boots, it’s just as important to avoid the style-traps that come with them. After all, there’s a lot of ways to pull off ankle boots depending on your style, height, type of trousers, etc. So, let’s break down the 4 main looks you’ll want to consider and talk about how to get them just right.

The Crop Trousers Look

For a lot of us, skinny jeans are simply a non-starter. That’s where you’ll want to turn to cropped trousers or even culottes. Ankle boots look better when the length of your legs is accentuated, so ensuring your trousers or jeans cut off at the right point can help even those of us with shorter legs pull off a great look. But where exactly should that cutoff be?

Opinions differ, but we’d say avoid jeans that cover up your shoes and go with a cutoff at least 2 centimeters (about .75 inches) above the boot. Some more daring styles with culottes will go 2-3 times higher up. Sometimes it looks fantastic, but it’s more of a high-fashion look that not everyone can pull off, so proceed with caution.

The Skinny Jeans Outfit

There’s just no denying it, skinny jeans with some leather ankle boots is just a great look. Fortunately, there’s a few ways to approach it. You can always tuck your skinny jeans into the boot. If your jeans are on the shorter side, you can also cuff or cut them and even show a bit of ankle (another great technique for making your legs look longer). Or, if you can’t cuff your jeans and they’re a bit shorter, letting them rest just above the boots to show that bit of ankle also works well.

The Friday Night Dress Look

While we tend to associate ankle boots more with trousers and jeans, they can look fantastic with a dress as well. The key element is again the length. Generally, dresses and African skirts look best with ankle boots when they, again, accentuate the length of your legs. So a shorter skirt or a dress which cuts off just below the knee work best because you still have some leg to show before hitting the boot. The only exception might be something very flowy with a vertical slit to get the same effect with a longer dress.

The Office Business Casual Outfit

One of the nice things about ankle boots is their ability to move seamlessly between more formal and casual looks. Now that doesn’t mean they’re for black tie events, but you can definitely go from business casual to Friday night drinks without a problem. Just about any heeled ankle boot will work here, just avoid the chunkier or western boot styles as those are a bit too casual. Bukela boots are a bit of an edge case and might depend on the outfit.

Suede or leather are perfect choices for that business casual transition. They could be clean single color or incorporate Oxford styling if you want something a bit more expressive but still appropriate for the office.

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