How to Wear Ankle Boots with Straight-Leg Jeans: The 411

In the iconic words of Nancy Sinatra: “These boots are made for walkin’ and that’s just what they’ll do.” You can walk, stomp, jump and dance the day away in a great pair of boots. Of all the varying styles, ankle booties are among the most versatile. They go with leggings, dresses and skinny jeans with total ease. Hold up—aren’t skinny jeans considered outdated right now? In some fashion circles, yes. With this in mind, it never hurts to try something new. We don’t encourage you to follow trends blindly but it’s refreshing to modernize your outfits from time to time. From high-end runways to everyday streetwear, looser-fitting jeans are taking the world by storm. Are you unsure of how to wear ankle boots with straight-leg jeans? Well, luckily for you, we’ve put together a collection of top tips to help you flex your fashion IQ.

Even though skinny jeans are on the back burner, they’ll always be a fairly simple clothing item to wear. In contrast, styling straight-leg jeans is notoriously a little trickier, especially if you’re planning to pair them with booties. Are you up for the challenge? Before you give it a go, take a peek at our insider fashion advice below to help guide you along the way.   

Pick the Right Jeans to Complement Your Booties 

There are a few routes you can take when deciding how to wear ankle boots with straight-leg jeans. Before anything else, you’ll need to figure out which style of jeans works best for the look you’re going for. A cropped pair of denim will show off your ankle or the peek-a-boo of a cute sock. However, if they’re too short, they can look like awkward capris. This is especially true if you’re on the hunt for the best jeans for tall women. A longer pair is more versatile. You can cuff them or cut a raw hem to customize the length. Whichever happens to be your personal preference, opt for a wider leg opening. Having more room around the ankle will allow jeans to layer over the boots without catching on the heel tab. 

How to Wear Ankle Boots With Straight-Leg Jeans: 3 Trusty Techniques

In fashion, rules are meant to be broken. You can wear whatever you want, however you want. With that said, it’s nice to avoid minor styling issues that can lead to major frustration. If you’re looking for guidance, having a fashion road map can make all the difference. That’s where we come in. Check out these three handy techniques for hacking how to wear straight-leg jeans with booties

1. Leave a Gap 

Alright ladies let’s dive into our first suggestion about how to wear ankle boots with straight-leg jeans. This technique may take a little bit of trial and error, but don’t let that discourage you. The goal is to leave a small gap between the bottom of your jeans and the tops of your boots. In other words, you want them to almost touch without actually doing so. Here’s an easy-to-remember rule of thumb: the longer the inseam of your jeans, the shorter the boot shaft should be. Capeesh? 

Want to know the perks of leaving a small gap? It allows airflow on warmer days and provides an avenue to master your personal style on colder days. As an edgy style gal, you can let your fishnet stockings have a moment. Is the cottagecore aesthetic more your thing? Dust off those cute forest creature socks that keep your tootsies warm all winter. 

2. Cuff the Hem

Technique number two regarding how to wear ankle boots with straight-leg jeans is arguably the easiest and most popular. A simple solution for jeans that are too long is to simply cuff the hem. Roll the bottom of your jeans (however many times you need) to take your look from sloppy to sleek. There are three different ways to do this. Firstly, utilize the pin-rolling technique where you cinch the excess material by vertically folding over the seam, then cuff upwards. This results in a tapered finish. Secondly, skip the pinching and create a large cuff by folding three to four inches at a time. Finally, cuff an inch or less of your hem for a low-profile look. We encourage you to give each of these techniques a try to see what looks best coupled with your booties. 

3. Choose Ankle-Hugging Boots

Opting for a sock boot is a no-fail solution when you’re unsure about how to wear booties with straight-leg jeans. Well, what is a sock boot, you ask? They’re a style of boot with a soft, sock-like material around the ankle. This allows the boot to hug your leg just like a sock would, which makes for effortless layering. Without the fuss, a slim-fitting bootie will slip right under the bottom of your denim. Alternatively, any ankle boot with a tall, fitted shaft will do. For an added streamlined effect, choose a pair without laces and instead, reach for a slip-on style or hidden zipper.  

How to Wear Flat Ankle Boots with Straight-Leg Jeans

Calling all ladies who prefer flats to heels. Are you wondering how to wear flat ankle boots with straight-leg jeans? The good news is that you can apply all of the same advice we’ve shared above. If you’re worried about adding height, go for a pair of platforms instead. This gives you a lift without the discomfort of heels. To further elongate your legs, match the shade of your shoes to your jeans. For example, black denim looks stellar with black booties to create the illusion that you have legs for days. Amplify this technique with a head-to-toe tonal look in a singular shade for a striking and sophisticated ensemble. 

How to Wear Ankle Boots With Straight-Leg Jeans for Ladies’ Night

Oh, yes, it’s Ladies’ Night, and the feeling’s right. Having a stellar outfit at the ready is key to maximizing on a good time with the gals. When deciding how to wear ankle boots with straight-leg jeans for your next night out, dare to go bold. Try those heeled boots that make you feel like a million bucks. Or, pull out those crimson red booties from your closet that you’ve been dying to wear. Feeling even more adventurous? Explore a current trend like the Americana aesthetic. After all, cowboy booties will keep you light on your feet throughout a long night of line dancing. 

How to Wear Ankle Boots With Straight-Leg Jeans to Work

Here’s one of the first questions you may ask when thinking about denim in the workplace: are jeans business casual? While it depends on a few factors, including your office dress code, a pair of non-distressed jeans is often suitable. With that said, dark- or black-washes are best. Since we’re talking about denim and footwear duos, are you wanting to know how to wear ankle boots with straight-leg jeans? To pull it off, keep an eye out for polished features. A slimmer straight fit provides a tailored effect similar to a well-fitting trouser. Next, skip the cuff method since it leans a bit too casual. This means finding a pair that’s the perfect length for you—right above the ankle bone. Finally, choose a pair of booties that offer a sharper appeal. Think of a pointed toe, patent finish and moderate heel height. 

How to Wear Ankle Boots With Straight-Leg Jeans on a Rainy Day

Depending on where you live and the time of year, avoiding puddles on a walk outside is almost impossible. Other times, it’s fun to forget your age and stomp in every puddle you see. Either way, we want our clothes to stay dry. Curious about how to wear ankle boots with straight-leg jeans on a rainy day and still avoid soggy pant bottoms? The cuff method is your best friend in this case. Pair your rolled jeans with all-weather booties with a slightly taller shaft than normal. Keep your look fun with an unexpected shade like teal green, pastel purple or neon orange. Bonus points for a pair of shearling-lined boots for maximum warmth on frigid days.     

Are you on the hunt for a new pair of ankle boots and straight-leg jeans? Our expert stylists are ready to lend a helping hand. To start, take your style quiz and order your first Fix. Five items will arrive on your doorstep, allowing you to try on everything in the comfort of your own home. Try before you buy, keep what you love and return the rest. While you wait for your pieces to arrive, head over to Stitch Fix Freestyle™ to find items selected for your style and size. Shipping and returns are always free. 

A New Way To Shop

Stitch Fix connects you with personal Stylists to send you looks you’ll love.

Get Your Fix

Need expert fashion advice?

Get a personal stylist

Want more tips, trends & insider news? Follow @stitchfix on Instagram