What to Wear With Women’s Ankle Boots

Finding the perfect pair of women’s ankle boots is like the holy grail of shoes! Something that you can throw on confidently, knowing that they’ll be both stylish and comfortable and provide that finishing touch to your outfit. You might not even know what you want to wear but are confident that with your favorite ankle boots on your feet, all will be well.

Is it possible though to find the perfect pair of ankle booties that will work with just about everything? What does it take to make the bootie work and are there any important do’s and don’ts that you need to be aware of? We’re going to be looking today at what to wear with ankle boots.

As with men’s dress boots, before we can begin to answer this question, we need to consider the different types of ankle boots that exist. It might be that a wedge works better with a dress while a pointed toe goes better with ankle-grazing jeans. So let’s run through some of the most popular types of ankle boots and what to wear with them.

The ankle boot is a versatile piece of footwear

When it comes to ankle boots, there are lots of distinguishing features that differentiate the styles, and while they might all generically be called an ankle boot on account of their length, they can differ quite dramatically. The most common options are the shaft height and style, the heel style and its height, the material type, and it’s color, what shape of toe your ankle boot has, including whether it’s an open or closed toe design.

You can get any combo of all these elements, and the overall final look will be significantly altered just by switching up a few of these critical factors, as will their suitability to be worn with individual styles of outfits.

Closed toe vs. peep-toe ankle boots

Whether you opt for a closed-toe or a peep-toe will affect how you style your ensemble and what you wear with your boots. The more popular and versatile choice is a closed toe as you can wear this style regardless of the weather. With a peep-toe, you will be limited to spring or summer as you’re unlikely to want to have your toes out during the colder winter months. This in itself already starts to dictate what you might wear with them.

Closed-toe shoes also have more options within that category itself with pointed, broad-rounded, and even roper-shaped toe-bed options. Automatically a pointed toe will elevate an outfit and make it look more refined and elegant whereas a very rounded-toe will lend more of a casual air, especially if you’ve also opted for a softer material.

Add on some embellishments and detailing though and once again, your boot can take on a whole new lease of life.

Let’s look at how to wear an ankle boot according to the height and style

One of the most significant limitations (or advantages depending upon how you choose to look at it) when you are styling an outfit, is the heel height. The block heel is a stacked heel, usually about 3 inches high and gives this kind of ankle boot a dressier feel, regardless of whether it’s made from leather or suede. It’s the height that brings the wow factor yet being a block style; this is also a more comfortable ankle boot to wear for more extended periods too.

You really can wear this kind of boot with just about anything, but some great recommendations for simple outfits are to team with rolled up jeans, skirts, and dresses or even a nicely tailored pair of shorts. The extra height of the block heel is great for elongating the leg and giving the illusion of length, but you won’t feel over-dressed. Everyone should have a pair of block-heeled ankle boots in their wardrobe.

Lower block heel ankle boots for every day

If you opt for a lower heel with the same block style design, you will have the perfect everyday wear bootie. This is a real style staple and the preferred casual boot of the majority of people on account of its comfort and versatility. Lower block heels look great with jeans, even double rolled-up hems to show off the boot but also with swing style dresses and skirts for a more casual, off-duty look.

If you find a pair you love, then pick them out in different colors or consider getting the same boot in both leather and suede. You won’t regret it, and the outfit options are endless.

What about the popular wedge?

While this has to be one of the most popular and fashionable styles of ankle boots, it’s not the most versatile or practical, but when worn with aplomb, they can create a seriously stylish, statement outfit. A wedge goes great with a pair of black leggings or skinny jeans tucked in so that you can show off the full design of the boot. They’re also super cute worn in the winter with thick black tights and an oversized jumper dress for a very chic yet casual daytime look.

How about styling up the stiletto heel ankle boot?

Automatically adding more va va voom to an outfit and elevating your look to a whole new sophisticated level, the stiletto boot never fails to look sensational and to deliver an upscale vibe. Best worn at night for when you want to make an entrance or know that you won’t have too much standing around to do!

A gorgeous dressy stiletto ankle bootie will go with a sharply tailored and tapered trouser suit, a pair of leather trousers or with a little black cocktail dress. This style of ankle boot will deliver a polished finish to a daytime look or bring real drama and elegance to your dressier nighttime styles.

A final thought about flats

No heel or flat ankle boots can be more challenging to carry off, especially if you happen to be on the more petite side. You definitely wouldn’t want to pair these kinds of shoes with anything dressy or glamorous.

The flat is best worn in the summer with shorts, in the spring with a swing dress and the winter with your jeans. This type of boot is also loved by the Boho self-styled girl who loves a long floating maxi style dress with a pair of strategic flats for a very casual but still chic vibe.


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