Style Guide: How To Wear Ankle Boots With Jeans

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Thinking of wearing ankle boots for that chic Parisian vibe? If so, check out this style guide on how to best wear ankle boots with jeans.

Imagine this: You just got home from the mall and you’re getting ready for a night out for margaritas with your best friends. When shopping, you stumbled upon a pair of adorable western-inspired ankle boots that you thought would be perfect for tonight’s occasion.

You’ve changed into your favorite jeans and cute top combo, zipped up your new booties, and are standing in front of the mirror thinking “WTF?”.

Something just doesn’t look as you had imagined and you’re in desperate need of some tips on how to style your new ankle boots with jeans. Well…look no further.

How to wear anle boots with jeans: pair them with a black leather jacket with crop top
Get this look on Princess Polly

When styling ankle boots, there are several tips and tricks to keep in mind. Remember that ankle boots can be worn all year round, no matter what the weather is doing. So don’t worry about spending a bit of money on a pair as you’ll definitely get great use out of your investment.

Now, lets get into the top tips about how to style your ankle boots for maximum style points, as well as a few things you should avoid.

How To Wear Ankle Boots With Jeans: The Do’s

1. Match your ankle boots with skinny jeans
How to wear ankle boots: pair them with skinny jeans and a sweater
Get this look on Pink Lily

Even though oversized, high-waisted jeans have become very popular over the last couple of years, ankle boots will always pair flawlessly with skinny jeans. When it comes to skinny jeans, there are usually two lengths: regular and cropped, both of which can be worn with ankle boots.

Regular-length skinnies can be worn as is, with the hem being hidden in the ankle boot. But with cropped skinny jeans, these take a bit more finessing. If the hem isn’t already rolled up, take the hem and roll it upwards about half an inch (the smallest roll you can make), and then do it again so you have two tiny folds.

This should reveal about one to two inches of your sultry, naked ankle before your ankle boot begins. If you’re not keen on the look of the rolls but want to show a bit of skin, jeans can also be rolled under.

Rolling your jeans into a cuff does give the look more of a casual vibe so we suggest avoiding the cuff if you’re heading to a formal event. For fancier occasions, try to go for cropped skinny jeans and ankle boots with a higher shaft or regular length jeans that tuck nicely into the top of the boot.

2. Pair them with mom jeans
How to style ankle boots with mom jeans: go for a relaxed fit sweatshirt
Get these jeans on Mint Julep

If you don’t feel comfortable wearing form-fitting skinny jeans, ankle boots can go with oversized boyfriend-style jeans as well. Ankle boots with a skinnier top and sock-style booties look best with mom jeans as they contract the wide leg of your jeans.

Pointed toe ankle boots also look really chic with oversized mom jeans as they elongate the appearance of your legs. With this style of ankle boot, you can roll up the hem of your jeans or let them hang naturally!

3. Exercise caution with wide leg or flared jeans
How To Wear Ankle Boots With Jeans: Style with white ribbed crop top and flare jeans
Get this look on Princess Polly

This is by far the trickiest style to pull off as only certain styles of ankle boots work well with jeans that have a flared hem. If you’re rockin’ this retro style of jeans, you want to avoid wearing ankle boots with a round toe as it will make you appear stumpy.

You’ll also want to try and find an ankle boot with a bit of a heel for some extra length. The optimal style of ankle boots to wear with flared leg jeans are pointed toe sock boots or pointed-toe boots with a bit of a heel. Western-style ankle boots would work as well.

Our Top Ankle Boot Outfit Picks

If you’re still in need of a little extra guidance, we’ve found three outfits with jeans and ankle boots that demonstrate all of the “do’s” on this list.

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Save these pictures to your phone and use them as a reference point next time you go shopping.

1. Casual

What we love about this outfit is that it looks super comfortable yet exceedingly trendy at the same time. Ankle boots are a footwear that can really be worn year-round, which is demonstrated by this outfit.

They can be worn with dresses and jean shorts in the summer and with leggings or jeans in the winter. Pair your ankle boots with some straight-legged jeans, toss on an oversized sweater, wool coat, and scarf and you’ll be looking very cold-weather chic.

2. Professional

Simply put, we love nothing more than the combination of a black top, blue jeans, and black boots. This look can be worn to the office and then out for happy hour drinks once the clock strikes 3 p.m.

If you’re wanting to elevate the look, add a belt with a detailed buckle and a pair of trendy statement earrings. While the model in this photo is wearing skinny, regular-length jeans that are rolled into a cuff, this outfit can also be recreated with mom jeans or flared denim.

3. For date night

Whoever said you have to show skin to look sexy was completely wrong and clearly never saw this outfit. The combination of the skin-tight, distressed black jeans and the brown leather jacket is extremely sassy and will capture the attention of your date and everyone else in the room.

This outfit is perfect for the fall and winter but if you’re wanting to create something similar in the warmer weather, wear a dainty tank top under the jacket.

4. For coffee with your friends

When you’re meeting your friends for a blueberry scone and vanilla oat milk latte at the local cafe, comfort is key. Wearing a pair of oversized, high-waisted jeans with a pair of ankle boots with a slight block heel will keep you feeling cozy while looking fashionable.

Since you never know if the temperature inside the coffee shop is going to be hot or cold, layering tops or bringing along a jacket is always a wise idea. If you’re wanting to up the ante, throw on a belt with stud detailing and a statement bag that you can shove your scone leftovers in when you head home.

The don’ts Of Ankle Boots With Jeans

1. Don’t let there be too much skin

You know how they say “less is more”? That most definitely applies to the amount of skin you have showing between the top of your ankle boot and the hem of your jeans.

As a rule of thumb, don’t exceed two inches. If your cropped jeans are just too short, you’ll need to purchase a pair of boots that go higher than your ankle or you’ll have to wear them with sneakers instead.

2. Don’t try to tuck in too much excess

If your jeans are way too long for you, don’t try to tuck them into your ankle boots as they will make the top of your shoes look funny. Wear your too-long jeans with your higher boots instead.

3. Don’t let your socks show

Even though you really love your bright pink socks covered in sloths, they won’t look super fashionable peeking out the top of your ankle boots.

When putting together your outfit, opt for ankle socks instead of regular-length socks unless you can push them down into your shoe. But whatever you do, don’t go sock commando as that could result in some seriously painful blisters.

Even though this article is about matching ankle boots with jeans, we have to include a few cautionary points to make sure you don’t commit any fashion crimes.

Avoid wearing ankle boots with A-line mini skirts (go for higher boots instead), long prairie-inspired dresses, structured suiting pieces, or overly baggy jeans.

Our Top Ankle Boot Picks

1. Lulus Ivory Pointed Toe Ankle Booties
White ankle boots from Lulus
Get these boots on Lulus

If you’re yet to own a pair of ankle boots, these pointed-toe booties are the best place to start. They come in six different colors, including ivory, light brown, dark brown, and black.

These adorable ankle boots pair perfectly with jeans and have a 2.5-inch heel, helping you out a little in the height department.

Each pair is made with vegan-friendly materials and has a lightly cushioned inside that will keep your feet happy. These boots only cost $54.

2. Free People Charm Double-V Ankle Bootie
Free People Charm Double-V Ankle Bootie
Get this on Free People

The Free People Charm Double-V Ankle Bootie is casual, trendy, and won’t go out of style for several fashion seasons. Each pair has two Vs cut out on either side, showing off your sexy ankles to the world.

They also have a short stacked heel that’s comfortable enough for everyday wear to school or the office and they come in camel, black, and ink (navy blue). These Free People booties can be added to your footwear collection for $148.

3. Lulus Lennon Black Patent Square Toe Ankle Boots
Lennon Black Patent Square Toe Ankle Boots from Lulus
Get this on Lulus

These ankle boots are a little less on the casual side and a little more on the dressier side but they can be dressed down if need be. Because these ankle boots have a square toe and are made with faux leather, they can be worn to a party, out for dinner, or to a work event.

Each pair has a 3-inch wrapped block heel so if you’re not comfortable walking in heels, perhaps opt for a pair that only has a 1- or 2-inch heel. Fashionistas searching for the perfect ankle boot can choose between two colors: black and ivory. The Lennon Black Patent Square Toe Ankle Boots from Lulus cost $45.

4. Chinese laundry Davinna Booties
Black ankle booties
Get these on Nordstrom

If you’re searching for a pair of ankle boots that are casual and appropriate to wear when you have to walk substantially long distances, the Davinna Boots are a must-have.

Plus, these ankle boots are as versatile as they get: you can pair them with any outfit that you have in your wardrobe! The Davinna ankle booties retail for $89.95.

5. Waylen White Ankle Boots from Lulus
Waylen White Ankle Boots from Lulus
Get this on Lulus

As mentioned above, these ankle boots are great for ladies who are looking for a shorter heel on their booties. These Chelsea style boots are crafted from faux leather, can be easily pulled on, and have a higher shaft, which is wonderful for wearing with cropped skinny jeans or mom jeans.

They have a 2.25-inch rubber block heel and a cushioned inside, making them comfortable enough to wear all day. The Waylen White Ankle Boots from Lulus come in black, ivory, and oxblood, and cost around $48.

We hope you found this ankle bootie and jeans styling guide helpful! For more similar ideas, make sure to check out the posts below.

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