10 Ways to Wear Ankle Boots

I love summer but it’s been a hot one so I am ready to start wearing layers and boots. It’s looking more and more like fall every day so I thought I’d throw together a post on one of my favorite trends for fall: the ankle boot. They are great for creating a long, lean leg while still being modern and fresh. I love that they aren’t as restricting or confusing as knee high boots but still give me some much needed height and leg length. They come in so many styles, heel heights, and colors so finding a pair that works for you is going to be no problem at all. As a boot they are versatile and can be paired with so many outfits which is great for this transition into fall as well as all through the cold season (California has a cold season?). Below I’ve compiled a list of my favorite ways to wear ankle boots and linked each photo to its respective blogger so you can check out their amazing style as well. Later on I will be posting my top picks for ankle boots.

With Cuffed Jeans

This is such a great look for transitioning to fall because you can pair it with your summer tops for a cooler look. Cuffing your jeans is a great way to break up the leg line in a modern way and add some dimension. For shorties like me this is a great way to create the illusion of a long lean leg because your eye is drawn to the cuff making the rest of your leg appear longer. Its a great, stylish way to break out your jeans and start working them into your wardrobe.

Over Socks

This look is hard to get onboard with because it conjured images of my parents in the 70s wearing ankle heigh hiking boots with thick wool socks and thick rim glasses (you know what I’m talking about!). The key is to choose socks that are thin so they don’t create a chunky ankle. It works well with skinnies or leggings and can be paired with a long top or even a dress. I love how bohemian and laid back this look can be without being straight-outta-REI.

With Shorts

Currently this is how I am wearing mine. I’m shamelessly holding onto the last rays of summer by refusing to give up my shorts. This is such a great look because it still gives you that long leg-line while showing off those toned summer legs your worked so hard for. Choosing an ankle boot that doesn’t cut straight across your ankle for this look is key because it helps to add length, for those who are already vertically blessed its a chic-er more polished look.

All Dressed Up

I love the idea of working booties into a dressy outfit to give it a more bohemian feel. Leather or suede just adds a little bulk and substance to a dressy outfit which is a break for the usual. The laid back, flower child look is coming back. Pick a bootie that has got some heigh to it to give you that dressed up feel. Pointed toe, country western, sleek black leather-there are so many styles that can work for a dressy outfit so play around and find which one works for you.

With Wide Leg Denim

Hands down this is probably one of my favorite ways to wear wide leg denim because it gives you that long lean leg and then flares out at the bottom to add some dimension. I have always loved the look so I’m so excited its in style. This is a great way to wear your ankle boots in an unexpected way. Not only are they perfect for replacing wedge sandals but they look great with bootcut/wide leg denim. Its a fun way to sneak them into yet another outfit. This looks great with a long cardigan or vest.

All Dressed Down

Pairing ankle booties with your summer dresses is a no-brainer. It’s the perfect way to take your sun dresses into fall while the weather is still warm. You still get that long leg while showing that bronzed summer skin that will be gone before you know it. Add a jacket or vest for some layering action and you are good to go. This is a great way to try out different styles of boots because casual dresses look great with both flat and heeled boots.

With Skinnies

The perfect pair of cropped or ankle jeans in the key to pulling off this look. You don’t want to cut off your ankle completely because that is what makes the long leg-line possible. Instead you want a pair that hits at or just above your ankle so there is a break before your boots start. Choose a boot that doesn’t cut straight across is key. This is such a great look for transitioning your jeans into your wardrobe because you can pair it with any top and still look put together. My favorite jeans for this look are Paige Denim Skyline Ankle, I’m a shorties so these are the perfect length for this look.

Over Leggings 

Black leggings are a great addition to your transitional wardrobe because they are flattering and comfy. I’m not going to address the issue of leggings not being pants and people choosing the wrong type of leggings because thats just too much for me to handle. Leggings look great with ankle boots because they give you that long lean leg by continuing into the boot instead of stopping at the ankle. They are thin enough to not bunch at the ankle and make it chunky which is a big issue with jeans. The look I posted above is the perfect way to wear them, faux leather leggings go to well with the suede boots and don’t look like spandex.

With a Maxi

This is another great transitional look to take your maxis into fall. I just love how long and lean it makes your leg while still maintaining that floor length hemline. They key is to choose a maxi that has a slit to show some skin or to choose one that ends just above your ankle boot. Having that bit of skin to break up the outfit keeps it form looking frumpy and bulky.

As a Statement

Pretty much your ankle boots can work with just about anything, its all about how you put it together. I love the idea of the classic ankle boot because it is versatile and easy to wear but sometimes you just need that pair that stands out. Details like fringe or buckles can be a great way to draw attention to your shoes and make them the focal point of your outfit.

Let me know in the comments how you will be wearing your ankle boots?


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