Ankle boots are a girl’s best friend. Seriously. What could be more functional and stylish than a chic pair of heeled booties? I own ankle boots in multiple colours because they’re so versatile and can be worn with pretty much anything. Jeans, leggings, dresses, skirts – all of these things and more, can be paired with ankle boots and look absolutely amazing. But there are certain ways to wear them that will bring you from stylish gal to full blown fashion guru!
Jeans, for instance, look great when you cuff them to sit on top of the bootie, but they don’t look so great tucked in. And A-line midi skirts look better with ankle boots than slick-to-the-body pencil skirts. When it comes to dresses, ones that come above the knee give off a girly yet edgy vibe when worn with ankle boots, and it’s a look I absolutely love! Leggings are probably the trickiest to master, but just make sure you wear them with tops that are flowy and reach below your behind. And the addition of leg warmers will give the leggings/ankle boot combo some stylish dimension.
Another great thing about ankle boots is that you can wear them in every season. They’re especially awesome for spring and fall, and if you put a good protector on them, they’ll see you through winter too! And while the mid summer day heat may have you living in sliders and gladiators, ankle boots are perfect for cool summer nights with a dress and light denim jacket.
From pants, leggings and jeans to dresses and skirts, here are some of our favorite ankle boots of the season as well as our best tips for wearing them with style.
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How to wear ankle boots with jeans
Ankle boots work with all types of jeans – slim, boot cut, boyfriend, destroyed, etc. but my favourite way to wear them is with skinny jeans. I always roll the cuffs so they sit at the top of the boot as I find that tucking them in looks a bit awkward.
Jeans are casual, so you if you want a cozy look you can throw on an oversized sweater or a plaid or white button-up shirt on crisp spring days. If you want an outfit that’s a little dressier, you can wear a cropped knit over a longer silk shirt. A sweater with an oversized scarf is also a great way to make a stylish statement with jeans and ankle boots.
For cool spring nights, a duster coat will pull together your ensemble, and a leather jacket with jeans is always a good idea. When it starts to warm up, throw on a plain white tee and accessories with dainty jewelry.
How to wear ankle boots with leggings
Leggings have made their way from fitness attire to everyday staple for some people, but you do have to be careful how you wear them. It’s best to wear a looser top that covers your bum – something to keep in mind both with or without ankle boots!
Kimonos are a great option to pair with leggings and ankle boots. They’re light, flowy, and there are so many beautiful designs to choose from! Pair a kimono with a lose yet structured top underneath, since the leggings are so tight to your body. You can also wear an oversized sweater or chambray button-up that covers your backside.
Ponchos are another great option for the cooler months, as are leg warmers! You can scrunch the leg warmers down so they sit just above the top of the boot. This gives some nice dimension to the outfit.
How to wear ankle boots with a dress
The dress and ankle boot combo is so darn cute! It’s actually one of my favourite looks. It’s feminine and edgy, and I find wearing them together usually gives off a slightly western vibe. If you like that country look, a pair of brown boots is best, coupled with a dress that comes above the knee, and finished off with a denim vest or jacket.
You can also wear a maxi dress with a slit at the side to show off the boots underneath, or one that comes right above the ankle. For spring, you can wear a dress on its own, or throw on a topper in the form of a light jacket, cool cardigan, or fancy kimono.
How to wear ankle boots with skirts
Similar to the dress and ankle boot pairing, skirts with ankle boots give you even more to work with. Skirts of all lengths pair well with ankle boots, and although I like the look of them better with A-line and flowy skirts, they can work with pencil skirts as well.
For cool spring days, wear tights with ankle boots and a mini skirt – I absolutely love that look! Wear it with a tucked shirt or untucked crop sweater or tee. Ankle boots also look amazing with midi skirts. I wouldn’t suggest wearing tights, though. Wear the combo with a nice blouse for a date night out, or a graphic tee for brunch with friends!
I’m also obsessed with suede fringed skirts right now -they’re perfect as we head into spring – and they look best with ankle boots. Tuck in a t-shirt or loose tank and take on the city in style!
How to wear ankle boots with pants
When wearing ankle boos with pants, it’s best to wear ankle grazing trousers that allow some skin to show. It’s a chic look, and worn with a structured top, is perfect for the office. You can also throw on a fitted or oversized jacket for a more business-casual vibe.
Another way to wear ankle boots is with flared pants. Either cropped or reaching down longer over the boot, flares nod to the seventies in a totally modern way. Keep your top more fitted since the pants billow out at the bottom, and you can even tuck the top into the flares for a pulled together look!
See? I told you ankle boots are versatile and can be worn with pretty much anything. All it takes is a little know-how and you can pull the look off with everything in your closet.
Well, almost everything…
