The time has come and I couldn't be happier.
I’m so excited that fall is here because the time has come for my ankle boots or booties to shine. Ankle boots are my favorite type of shoes for the colder seasons!
They are super stylish and can be comfortable too. I personally walked miles in my ankle boots until I visibly wore out the bottom soles! 😅
I’ve owned quite a few pairs over the years. My fall and winter shoe collection would not be complete without them.
That’s why I’m super excited to cover how to wear ankle boots with jeans! Ankle boots and jeans are the ultimate street-style chic combo. Plus, there’s an endless playground of styles and fits–for both jeans and ankle boots–to experiment with.
I’m going to cover in-depth everything you need to know on how to wear ankle boots with jeans–starting with the types of booties all the way to cuffing jeans.
I will also include cute outfits on how to wear ankle boots with jeans that are ready for immediate copying.
Let’s dive right in!
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In This Post ➜
- 3 Types of Ankle Boots You Need To Know
- What Kind of Jeans Go Best With Ankle Boots?
- Ankle Boots + Skinny Jeans
- Ankle Boots + Straight Jeans
- Ankle Boots + Wide Leg, Bootcut, & Flare Leg Jeans
- How To Wear Ankle Boots When You’re Over 50
- How To Wear Ankle Boots With Jeans As A Plus Size
- Frequently Asked Questions
3 Types of Ankle Boots You Need To Know
There are tons of ankle boots styles out there, but they typically come in 3 different ankle or shaft heights (the part that goes up the ankle). The shaft height of ankle boots will make a difference on whether you would tuck in your jeans or not.
Familiarize yourself with these 3 types to make your ankle boots styling experience easier:
- Low Booties
These ankle boots have a shorter shaft that hits below the ankle bone.
- Medium Booties
This is the most common type of ankle boots. The shaft rises about an inch above the ankle bone.
- Tall Booties
These boots have a taller shaft that is a few inches higher than medium booties.
What Kind of Jeans Go Best With Ankle Boots?
Jeans in general look great with ankle boots, but certain styles and fits will work better together than others. It’s also crucial to know when to tuck jeans into boots, cuff them, or do nothing at all.
Keep reading to learn about the different types of jeans and how to style them with ankle boots!
How to Wear Ankle Boots with Skinny Jeans
Skinny jeans are the most flexible when it comes to pairing them with ankle boots. They can be tucked in, cuffed, or left alone depending on the length.
The primary goal is to prevent the jeans from bunching too much–creating a puddle of fabric at the ankles. Not a cute look, right?
Unlike other jeans, skinny jeans hug the legs and fit closer to the ankles. This reduces any fabric bunching.
However, if the jeans bunch at the ankles, it probably means they’re too long. There are two options to reduce bunching:
- Tuck in the jeans into the ankle boots. This will naturally create long, lean lines and streamline the legs.
- Cuff the jeans above the ankle boots, so the hem hits right above the booties when standing still. Some skin should peek through as you move around, which will highlight the narrowest part of your leg and avoid making the legs look stumpy.
I’m a fan of the small single cuff or the double-cuff. The cuff should generally be about one or two inches high. This is equivalent to no more than two or three fingers high in width.
If the jeans end right above the ankle boots, feel free to leave them as they are. This is usually the case with cropped skinny jeans.
Ankle Boots + Skinny Jeans Outfit Ideas
Chelsea ankle boots are timeless and sleek. They look great with skinny jeans!
Alternatively, chunky lug soles or combat boots will add an edgy vibe to the outfit.
Tuck in these skinny jeans for a slimming and lengthening effect.
Keep it edgy and cool with a moto jacket. They look great with ankle boots!
Alternatively, make it casual and comfy with a long neutral cardigan and white tee.
How to Wear Ankle Boots with Straight Leg Jeans
Straight leg jeans are today’s modern jeans. It’s not quite as form-fitting as skinny jeans, but they’re loose enough to highlight curves and be comfortable.
However, be careful when shopping for straight leg jeans. Retailers tend to throw the term around, but they don’t always mean the same thing. Plus, the fit varies across brands.
Test whether the jeans are truly “straight leg” by taking the bottom hem and folding it up to the knee. If they’re the same width, it’s a straight-leg. However, if the width of the hem is wider, then it’s more likely bootcut jeans. If it’s shorter, then more likely skinny jeans.
It’s actually incredibly easy to style ankle boots with straight jeans. They don’t need to be tucked in or cuffed. Simply let the hem skim over the ankle boots.
If they have a cropped length, make sure there isn’t a gap larger than an inch between the hem of the jeans and top of the boots. A large gap can cut off the leg line and establish an awkward, unflattering look.
Ankle Boots + Straight Jeans Outfit Ideas
Block heel ankle boots are incredibly stylish and look so high-fashion with straight-leg jeans. Plus, the block heel elongates the legs and is much easier to walk in.
Get a pair of pointed ankle boots add an extra leg lengthening effect and look so modern.
A classic pair of straight-leg jeans is very street-style chic.
Pair it with a slimming knit blouse for a casual, but refined look.
A denim jacket is a closet staple and will look great layered over the blouse.
How to Wear Ankle Boots with Wide Leg, Bootcut, & Flare Leg Jeans
Wide leg, bootcut, & flare leg jeans are not the most popular option for ankle boots, but they can look incredibly high-fashion when done right.
They’re the easiest to style with ankle boots because you don’t have to cuff them or tuck them in. The wider leg opening at the hem just doesn’t allow that. Simply wear them over your boots!
The key here is to wear a longer length that covers the top of the boots and ends midway down the back of the heel. Avoid jean lengths that bunch up near your toes or drag on the floor.
Also, make sure the shaft (the part that goes up the ankle) of the bootie is under the jeans. You also want the shaft to hug the ankle closely. Sock booties would be a great option in this instance. You don’t want the hem of your jeans to get caught on top of your boots!
Although wide leg, bootcut, and flare jeans share a similar wide bottom hem, there are specific differences that you should be aware of:
- Bootcut Jeans
Bootcut jeans are slimming from the hips to the thighs and have a slight flare from the knees to the ankles. They are narrow at the knees in comparison to the leg opening.
- Wide Leg Jeans
Wide leg jeans are wider at the knee and leg opening. They have a slightly more relaxed fit throughout the legs.
- Flare Jeans
Flare jeans are similar to wide leg jeans, but they are narrower at the knee. There is a bigger difference in the knee and leg opening, which gives it that “flare” effect.
Ankle Boots + Bootcut, Wide Leg, & Flare Jeans Outfit Ideas
Sock booties hug the ankles closely, which creates a slimming and lengthening effect. Perfect for jeans with a wider leg opening!
Obtain the high-fashion look by letting your jeans drape over your boots. This will also make your legs look longer.
Wear a form-fitting top to balance out the wider bottom-half. A cute off-shoulder top would do the trick!
Alternatively, make it a cozy outfit with a cropped sweater instead.
How To Wear Ankle Boots When You’re Over 50
Just because you are older, doesn’t mean that you have to give up wearing ankle boots! There’s no rule or limit on when you should stop wearing ankle boots.
I know that I will keep wearing ankle boots for as long as I possibly can, so don’t be afraid to wear ankle boots with jeans, even if you’re over 50.
The real question is–how do you wear ankle boots with a more sophisticated or mature look?
Here’s a few easy tips to help you find the perfect ankle boots when you’re over 50:
- Look for ankle boots in a neutral color, such as black, gray, taupe, and brown. These colors are sophisticated, timeless, and coordinate well with any outfit.
- Avoid any trendy and loud embellishments, such as spiky studs or tons of faux fur. Small details, such as some lacing or flat studs are ok. You don’t want to feel like you’re wearing outrageous runway shoes.
- Look for ankle boots with a block heel for casual everyday looks and one with a medium stiletto heel for dressier events.
- Pay attention to the toe shape. Round toe shapes are classic and great for just about any occasion. Pointed toe shapes are great for dressier events.
- Tuck in your jeans if they’re long enough. If your jeans are short, feel free to leave them hanging over the ankle boots or cuff them about ½ inch above the boots.
How To Wear Ankle Boots With Jeans As A Plus Size
Ankle boots look great on any body type and size! They can help elongate and make your legs appear slimmer.
The key to wearing ankle boots with jeans as a plus size is to know when to tuck in or cuff the jeans. If your jeans are long, tuck them in. You’ll know that your jeans are long enough if the tuck doesn’t come undone when you walk.
If they are a bit shorter, try to cuff them about ½ inch above the boots. Don’t cuff them too high or your proportions will feel off!
I also recommend getting ankle boots with a block heel. It doesn’t need to be very high–even 2-3 inches would work. The heel really helps lift and elongate the legs, which can be very flattering for plus sizes.
Finally, when shopping for ankle boots, look for boots with a wider shaft or opening. A good tip is to specifically look for ankle boots designed for wide feet. This would make it easier to slip into and more comfortable while walking.
Frequently Asked Questions
Where Should Jeans Sit With Ankle Boots? (Roll Or Tuck?)
The part where your jeans end and when the ankle boots begin tend to draw the eye’s attention. Therefore, it’s crucial to know when to tuck in your jeans, cuff them, or just let them hang over the boots.
The general rule is to leave about a ½ inch to 1 inch of your ankle showing above your ankle boots, if you cuff them. You also have the option to tuck your jeans in, if they are long enough to stay securely tucked in all day.
Skinny jeans are generally easier to tuck into ankle boots because they fit very close to the ankles. However, you can also roll or tuck them about ½ to 1 inch above your ankle boots if they’re too short to tuck in.
Moreover, you can leave your jeans hanging over the ankle boots. This generally works well with straight-leg jeans or jeans that have a wider bottom hem.
Just make sure that the jeans don’t bunch up when you leave them over your boots. The extra bunched up fabric can be unflattering.
Are Ankle Boots Still In Style For 2022?
Yes, ankle boots are still in style! They seem to defy any trends and are timeless shoes. While I cover the many different ways that ankle boots can pair with jeans, they also go great with dresses, shorts, skirts, and pants.
They’re also very versatile and can be worn for almost any occasion–from everyday casual to dressy events.
Ankle boots come in a variety of different toe shapes, heels types, colors, patterns, and embellishments. There’s so much room to play around with. Ankle boots are not retiring in the fashion scene anytime soon!
Why Is Styling Ankle Boots With Jeans So Confusing?
I get it, it’s super confusing! There’s a variety of jean styles and fits. Ankle boots also come in many colors, styles, and shaft lengths.
The key to styling ankle boots with jeans is to familiarize yourself with the basic styles first. Review the main types of jeans that I listed above. Moreover, know when to cuff, tuck in, or do nothing with your jeans.
The key to styling ankle boots with jeans is to familiarize yourself with the basic styles first.
Everything you need to know about styling ankle boots with jeans is in this post. Read through my tips to understand how ankle boots and different jeans work together. You’ll be well equipped to style your next outfit!
Do You Wear Boots Over Or Under Jeans?
You can wear boots over or under jeans, but it depends on what type of jeans. For skinny jeans, I recommend wearing boots over jeans to create a long, lean line that elongates the legs.
If they are cropped skinny jeans, the bottom hemline typically falls above the ankle bootie, so you can leave it as it is. You can also cuff the bottom hem of skinny jeans so that the jeans end above the ankle boots.
In addition, wear boots under jeans for straight leg, wide leg, flared, and bootcut jeans. It’s better to wear boots under jeans when the jeans’ leg opening is wider.
Do You Wear Socks With Ankle Boots?
Yes, I highly recommend wearing socks with ankle boots for hygiene purposes! Our feet will sweat over time and this can make your boots stink.
Wear socks that have antibacterial properties and wicks away moisture to prevent odor-causing bacteria from growing. Also, a good pair of socks prevent blisters and sores. They will provide some cushioning and keep your feet dry in warmer weather. Trust me, your feet and nose will thank you.
Yes, I highly recommend wearing socks with ankle boots for hygiene purposes!
Moreover, ankle boots are a great way to show off cute socks. Add a pop of color or cute pattern by letting your socks peek out from the top of the boots.
If you want your socks hidden, wear colors that match your boots. Moreover, you can fold the socks down if they are too long.
Should Ankle Boots Be Tight Or Loose?
A good pair of ankle boots should be tight enough to support your foot, but loose enough to let your foot flex. The goal is to find a pair that fits you just right. It shouldn’t be too tight or loose.
Leave enough room in your boots for socks. If the boot is a little loose, you can compensate by wearing thick socks or insoles. Ankle boots that are too loose will cause blisters, heel slippage, and chafing.
Can I Wear Ankle Boots With Leggings?
Yes, ankle boots can be worn with leggings–even jeggings too! Similar to skinny jeans, leggings are body hugging. They accentuate your curves and help make the legs appear slimmer.
The best part about leggings is that they make it super easy to tuck into your ankle boots.
In fact, you might not have to do anything since leggings fit so tightly around your ankles–just slip into your ankle boots and you’re done!
Disclosure: This post may contain affiliate links, meaning I get a commission if you decide to make a purchase through my links, at no cost to you. Please read my disclaimer for more info.
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