6 Tips for Styling Ankle Boots

Striking the perfect balance between functional and fashionable, we know there’s a good chance that your cute ankle boots act as your all-rounders that you wear every day for every activity — which is why this isn’t a “Ways to Wear Ankle Boots” article that tells you what to wear them with. We aren’t here to change your wardrobe, change your look or rob you of the stamp that you put into your style. Instead, we’re here to help you rock your ankle boots with any outfit as easily and as effectively as possible. Whether you’re dressing up for a night out on the town or dressing down for a day out on the hiking trails, our tips remain the same!

Pick the Perfect Pair

Picking the perfect pair of ankle boots will be the most important step in styling them successfully. This will allow you to make outfits around them as easily as you can make outfits and add them. To find your most flattering and new-favorite booties, consider the following with your fashion desires and functional needs equally in mind. Along with finding the perfect pair, this will also help you understand outfit compatibility and what features may be impacting your outfit! 

  • Ankle Height: The top of your boot will create a solid line across your leg, so the more narrow or wide that line looks, the more narrow or wide your legs will look overall. Generally speaking, this means that the most flattering boot height will be one that cuts across a narrower part of your leg — but it all depends on what you want to showcase!
  • Ankle Width: Styles that hug the leg with a slimmer ankle width are for you if you tend to wear jeans or pants that are cropped or wide, as they sit perfectly underneath the ankle. Wide ankle booties, on the other hand, will suit the skinny jean wearers well as they will allow you to tuck your jeans inside them with ease. 
  • Heel Height: Comfortable heels for women can compliment any outfit and can go a long way if you’d like to elongate your leg and blend your boot into your outfit. A flat ankle boot, on the other hand, can have a shortening effect on your appearance (and clear comfort) that is adored by many.
  • Heel Shape: A slim heel such as a stiletto can look unbalanced on those who carry more of their weight on the bottom half. Likewise, a chunky heel can look unbalanced on those with very slim legs. While this can always be balanced through your outfit, purchasing a proper balance will mean that you don’t have to!  
  • Toe Shape: Pointed toes tend to elongate the legs, while rounded and square toes tend to shorten them. Style-wise, a pointed toe may be easier to dress up, and a rounded or squared toe will likely create a much more casual look. 

Create a Coherent and Balanced Style   

For this tip, we will use hiking boots as an example. Hiking boots have an awesome utilitarian aesthetic. To blend and balance this aesthetic with your own (and MAKE it your own), you’ll want to pair it with something equally casual and functional, but incorporate a complementary and possibly even contrasting aesthetic like very fashion-forward pieces and accents. As an example, you could combine your functional and casual hiking boots with equally functional and casual jeans and crew and then balance the look with a cute and fashionable scarf, earrings and socks poking out from over your boots. In this case, adding a fashionable element ensures that the functionality of the hiking boots is well-balanced. 

If the masculinity of the boots is what catches your eye more than the utilitarianism, then consider contrasting that in a complementary and coherent way — for instance, by incorporating feminine pieces, accents and colors. Likewise, if these aesthetics are true to you and you plan on fully embracing them, then do it wholeheartedly! No matter what the boot is, it’s about identifying what it showcases and either rolling with that style or integrating it with your own in a coherent and balanced way. In other words, you can’t implement a style through your footwear alone.

Blend Your Colors 

Even when you’re working with an outfit where its saving grace is a long stretch of leg in between your bottom hemline and the top of your boot, you still want to put the effort into blending your clothing and boot colors. If you’re particularly good at creating balance, beautiful boot and top combos can absolutely be created; otherwise, it’s a good idea to stick to a simple tried and true tip: black boots pair best with black or gray bottoms, whereas beige, tan and brown boots should stick with like shades of beige, tan, brown and cream. We recommend finding washable shoes for women to preserve colors when possible!

Balance Bottom Hemlines and Boot Heights 

When it comes to how far down the hem of your pants, skirts and dresses fall, you likely know your personal preferences and have come to learn what’s flattering on you. If you’re one of the people from above who’s been wearing your ankle boots to their full potential, though, you’ve probably had your perception of hemlines changed. 

This is because when you wear your ankle boots often, you run into problems pairing them even more often — and you come to realize that where the hemline of your bottoms fall will make a MAJOR impact on the way your boots look, and how high up the leg your boot comes will make a MAJOR impact on how your bottoms sit and look. 

As a rule of thumb, you should keep a sliver of skin showing between the top of your boots and the bottom of longer skirts and dresses, as well as with loose and flowy pants. If the overall look is still too heavy, consider pants, dresses or skirts that have a slit up the side to allow for more open and airy gaps between pieces. 

If You’re Still Struggling… Start From the Bottom  

Your shoes set the tone for your ensemble — and in the case of the ankle boot, it can often be a tone that’s hard to harmonize with. If you find yourself struggling still, it helps to start styling from the shoe up. Starting with whatever boot you want to wear will allow you to dress proportionately to your boots much easier, and even possibly begin to have some fun with it in the process. If your boots boast any bright colors, stylish silhouettes, bold details or striking accents, this holds especially true!

Anshu Dev: Internet trailblazer. Travel ninja. Social media evangelist. Incurable explorer. Subtly charming organizer. Tv scholar. Alcohol geek. Certified creator.

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