Come fall and winter, a pair of boots and jeans are a go-to outfit combination. Boots are also essential in the colder months to keep your feet warm and dry in the elements. No matter where you live thought, having great boots in your closet that pairs with all your jeans helps to make getting dressed easier.
There are definitely certain boots to wear with certain types of jeans. Not every boot can go with every style of jean, but some boots can go with many. I’m here to break them all down for you so you can easily shop for the right boots to work with your most loved jeans. Or find the jeans you need to pair with your favorite boots in your closet.
9 Boots To Wear With Jeans
One of the main things I want to emphasize when choosing new boots for your closet in these current style times, is to keep shaft height in mind. In the early 2010s, the low shaft boot was all the rage. A skinny jean paired with an ankle boot that showed off some skin. We are not doing that anymore. Many of our denim styles now are ging to work best with a slightly higher boot shaft. Keep this in mind when shopping to ensure your boots and jeans work well together.
Flat Chelsea Boots
A Chelsea boot is defined as an elastic sided ankle boot. They come in so many styles too. A flat Chelsea boot is a common option to pair with your jeans from skinny jeans, to straight leg. Flat Chelsea boots can come in a sleek design, or a more lug sole chunky silhouette.
This style works best with skinny jeans, pending the shaft of the boot goes up high enough, and straight leg or wide straight leg slightly cropped jeans. You can maybe get away with a flat Chelsea boot if it has an elongated toe box and pair with a wide leg jean.
- Skinny Jeans
- Straight Leg Jeans
- Wide Leg Cropped Jeans
Heeled Chelsea Boots
The Chelsea boot also comes in heeled versions and can vary from casual heeled boots with chunky soles, to more feminine and dressier options with stiletto heels and pointed toes. For the most part, a heeled Chelsea boot can work with your favorite super wide leg jeans, straight leg and even a skinny. It just all depends on the shaft of the boot. If it’s super snug to the body, I’d skip the skinny pairing. But if they’re a wider opening, they can work with just about every jean style.
- Skinny Jeans
- Straight Leg Jeans
- Wide Leg Cropped Jeans
- Wide Leg And Flared Jeans
Ankle Boots
Ankle boots are going to be a lower cut boot that hits around the ankle. They don’t go high up on the leg which limits their use with many of the current denim trends. In the early 2010s, we wore the ankle boot with skinnies, but that look is long over. Instead, you can still wear your ankle boots with wide leg jeans that cover the boot. When I think about how to wear ankle boots in the current trends, I’m mostly skipping over them. Out of all the boots on this list, these are the most outdated.
- Wide Leg Jeans
- Flared Jeans
- Full Length Straight Jeans
*Notice we are covering the entire shoe here…that’s on purpose.
Knee High Boots
A knee high boot is a favorite option to pair with some of my jeans. A pair of knee high boots are perfect to style with skinny jeans. I know I’ve said to get rid of the skinny jeans (for the most part) and it’s for this exact reason. I’d stick to dark wash skinny jean share. But a knee high boot really is the perfect pairing. You can also wear your knee high boots under wide leg jeans. They add a layer of warmth as well which is a total plus in cold weather.
Flat boots, or riding boots, and really any other style, work well with a skinny jean or a slim straight leg. And to pair with wider leg options, I’d stick to heeled knee high boots and ones that have a pointed or somewhat elongated toe box for a perfect pairing.
- Skinny Jeans
- Straight Leg Jeans
- Wide Leg Cropped Jeans
- Wide Leg Jeans
Combat Boots & Dr Martens
Combat boots and Dr Marten’s are a great option to style with your straight leg jeans or wide leg cropped jeans. Choosing a slightly cropped pair of jeans is key to showing off the boot a little as these are a heavier style and more chunky, so showing off the ankle of the boot helps to create more shape and doesn’t overwhelm the whole outfit with more denim puddling over it.
- Skinny Jeans
- Straight Leg Jeans
- Wide And Straight Leg Cropped Jeans
Pointed Toe Booties And Elongated Square Booties
A pointed to bootie is a great option for just about every jean style. Pointed toe boots are great because they elongate the body and feel a bit dressier. I’d wear these under the jeans so having the shaft of the boot more snug to the body is key.
- Straight Leg Jeans
- Wide And Straight Cropped Jeans
- Wide Leg And Flared Jeans
Heeled Booties
Heeled booties can come in so many styles. From classic stiletto and pointed toe versions, to Chelsea boot styles. It will depend on the shaft height and style of the boot to determine what type of jean these will work with. But generally speaking, most will have a slightly higher shaft and will likely work with all jean styles except skinny jeans.
Cowboy Boots
A cowboy boot can come in a few variations from a shorter boot to a taller one and have really unique details and designs on them. These are really fun to pair with skinny or straight leg jeans to wear over them. And for a cropped straight or wide leg to show them off.
- Skinny Jeans
- Straight Leg Jeans
- Wide And Straight Cropped Jeans
- Wide Leg And Flared Jeans
Sock Booties or Glove Booties
A sock bootie or glove bootie is a boot that is usually made out of softer material and hugs the ankle and leg. These are best with straight leg jeans so they slide nicely under your jean and are tight to the body.
- Straight Leg Jeans
- Wide And Straight Cropped Jeans
- Wide Leg And Flared Jeans
How To Wear Boots With Jeans
Let’s dive into how to wear boots with jeans with some more examples. There’s so many jean styles to choose from, but these seem to be the most popular. You can probably combine kick flare with your straight leg along with boyfriend jeans. Use this jean style guide to better understand fits too.
Boots To Wear With Wide Leg Jeans – Full Length Jeans
Style With A Heel
For your super wide leg jeans that are full length, think bell bottoms and flares, these are your best boot options. I like a heel best with these to help elongate your legs and usually, these jeans are longer and need a heel. But depending on your height, you may choose not to which is totally fine.
Elongated Toe Box – Pointed Toe Or Elongated Square Toe
The other general rule of thumb I like to apply here is an elongated toe box if possible. Pointed toes or elongated, rounded or square toes peeking out of the bottom of your jeans helps to elongate your leg and not have the jeans just cut your outfit off at the bottom by hiding your shoe entirely. The only time I think a more chunky and rounded toe boot works, is when it’s more of a slim wide, and not super wide. When you have lots of fabric combined with chunky heavy shoes, it can feel a bit messy. But a slim fit or tailored leg can sometimes work with the right rounded toe boot.
Try A Knee High Boot
Since wide leg jeans are loose from the knee down, you can get away with any shaft height here. You can even do knee high boots to get even more use out of them and keep you warm in the winter.
Boots To Wear With Slim Straight Leg Jeans
Ensure Your Jean Goes Over The Bootie
A slim straight leg jean is going to be similar to a skinny but slightly relaxed in the opening. These are your most simple denim update from the skinny jean. Another option that works with these boot options too are the kick flare jeans. The trick with these is to ensure your bootie is going under the jean and up your leg enough to not expose your skin when standing. You’ll see sock booties or glove booties that have a higher more snug shaft, and these are perfect. Any heel height works here as well.
Pair Knee High Boots With Straight Leg Jeans Too
You can also pair your slim straight leg jeans with your knee high boots. This is the best option if you got rid of your skinny jeans and want to still do jeans with knee high boots. In the above image, the knee high boots are to be worn on the OUTSIDE of the jeans, the others are to be worn UNDER the jeans.
What Boots To Wear With Skinny Jeans
Knee High Boots Are Best With Skinny Jeans
While we have been saying the skinny jeans are out, and the straight leg is in, you can still keep a pair or two. I’ve been preaching that since day one when we did our major Millennial style swaps. Knee high boots are perfect to pair with skinny jeans. We know that combination well.
Choose Slightly Taller Boot Shafts When Wearing Booties
But for your shorter boots, I’d still opt for a slightly taller boot shaft. We are not doing short ankle booties where our ankles are actually exposed. You can see all of these ankle booties are a bit higher over the ankle making them perfect to pair with skinny jeans. And yes, the boot goes OVER the jean!
Boots To Wear With Wide Leg Cropped Jeans
Whether it’s a wide leg cropped, or slim straight crop, the boots are fairly similar here. You can maybe get away with a knee high if it’s comfortable, but otherwise, these are my favorite style of booties to pair with either options when they are cropped around the ankle.
Fitted Taller Boot Shafts Work Best
You’ll want to find booties that go up on the leg and have a higher shaft to cover your skin when standing. You don’t see these more combat or Chelsea lug sole style boots paired with a wide leg full length, but are styled here with a cropped, because you show off the ankle of the boot.
The thinnest part of the boot and your outfit gets shown which helps to balance the proportions. If you wore a pair of boots that were more chunky with a rounded toe with a wide leg full length jean, you would look sloppy at the bottom. It’s a look you can do, but I think this style of boot works best with a slight crop. This is a similar rule we hear a lot if you’re wearing oversized clothing, show off your ankles, wrists and neckline. The same rule applies here with chunky boots paired with jeans. Show off the thinnest part of the silhouette to create balance.
There you have it, your ultimate boot and jean pairing guide. Are there any other boot or jean styles you have questions about?
