6 Foolproof Skirts, Pants, and Dresses to Wear With All Your Ankle Boots

In order to make my stories as helpful as possible, I often reach out to my close friends and colleagues to find out what it is they are struggling with fashion-wise. Sometimes, they need help tracking down the perfect pair of jeans at a certain price point, and other times, they want to know about all the latest trends, but this time, I will admit I was a bit surprised by their current conundrum. It seems that figuring out just the right pieces to style their ankle boots with is proving to be rather difficult, so naturally, I started writing a story on it.

Ankle boots are a wardrobe workhorse, so styling them should be a no-brainer, but the more I thought about it, the more I understood the specific points of confusion that could arise, including flattering hemlines, seasonally appropriate pairings, and everything in between. Ahead, I gathered a handful of outfits that break down the easiest ways to style your ankle boots thanks to some of the industry’s most stylish influencers. So sit back, relax, and get ready to take note of the foolproof ankle boot outfits you need to re-create ASAP.

The length of your skirt is everything when it comes to ankle boot styling, and it just so happens that miniskirts will work with any ankle boot style time and again. This season, stay on trend and try a tweed skirt suit to make even your most basic of ankle boots feel forward.

Midi skirts might be my favorite option to wear with ankle boots. The duo seems to work on a variety of body types and heights, making it a foolproof seasonal outfit to keep on heavy rotation in your closet. Yes, knee-high boots also look incredible with midi skirts, but ankle boots will also do the trick. 

There is nothing sleeker than crisp tailored trousers and cool ankle boots. While more traditional pointed-toe block heels might be your first instinct, we are loving the way chunky lace-up boots look with the classic pant style, especially for winter. 

Jeans can sometimes be the trickiest item to pair with your ankle boots due to varying hems and shaft heights. To ensure your pants always hit your ankle boots just right, opt for a longer pair of jeans that will cover most of the boot, leaving out just the tip of the toe. Trust me.

Mid-length dresses are always going to be your best bet when it comes to ankle boot styling. To ensure you aren’t distracting too much from the dress you’re wearing, we suggest opting for a simpler boot shape that skims the natural line of your leg and ankle, creating sleek proportions with your frock of choice. 

Even in the cooler months, minidresses can be one of the most useful pieces in your wardrobe. Throw on an oversize blazer and platform ankle boots, and instantly, even the most summery dress becomes seasonally appropriate. 

Next up, shop the designer items that are about to go viral in 2020.

The Under-$40 Pants That Will Rival Your Jeans This Winter

Okay, we’ll never fully give up on our jeans. After all, they’re the ultimate staple in our closets and half of our outfits depend on them. But this season more than ever, there’s a rising trend that’s threatening to knock denim off its sartorial high horse. Enter the wide-leg pant trend. From Valentino to Chanel, we saw loose, languid trousers dominate the F/W 19 silhouettes, and fashion girls are only confirming our suspicions, as we’ve spotted them prioritizing the luxurious-looking pants over their beloved jeans.

As we do pretty often when we spot emerging trends, we took it upon ourselves to design our very own version of the wide-leg pant trend for our Who What Wear collection at Target. Thanks to its high waist and satiny-silk texture, our Silky Wide-Leg Pants rival any of their expensive counterparts. Not only are they a cool option to elevate your outfits this fall and winter, but they clock in at just under $40, so there’s no reason not to try them out for yourself.

Keep reading to see how the trend emerged on the runway, fill up on outfit ideas from some of our favorite fashion girls and then, of course, shop our affordable version.

Suiting was given a slouchy update on the Valentino runway. In all-over cream hues, the look feels particularly current.

At Max Mara, thin turtlenecks were tucked into tailored trousers and styled with leather boots. It’s an outfit that we can easily re-create at home, barring the utility accessories, of course.

Chloé models donned long, loose trousers with utility pocket details.

Also available in more sizes.

Also available in more sizes.

Also available in more sizes.

Also available in more sizes.

Also available in more sizes.

Also available in more sizes.

Not quitting your jeans anytime soon? Let these denim outfits from Rihanna, J.Lo, and more celebs inspired you.

PSA: Free People Is Having a Flash Sale, and We’re Running

Holiday party season is all fun and games until you glance at your fridge and see invites for your company party, Friendsgiving, Thanksgiving, New Years Eve and…you get the point. But panic really sets in when I think about all the looks I need for each (I don’t want to be known as a serial outfit repeater!) on top of all the gifts I still need to buy.

But, it’s a holiday miracle: Free People is offering 20% off all purchases over $250 and 25% off all purchases over $500 for one day only. So, yeah, I’m scrambling to get all of my outfits (and presents) checked off my list so I can just chill for the rest of the season. Looking to do the same? Keep scrolling to see all the things I’m eyeing. 

Shop now and get 20% off your purchase when you spend $250+ and 25% off when you spend $500+. 

Up next, Taylor Swift Wore a Cozy Free People Dress With Designer It Boots.