What Shoes or Boots To Wear with Your Jeans – A COMPLETE Guide!

What Shoes To Wear with Jeans

I’m betting this style dilemma has happened to many of you… you’re standing in front of the mirror wearing your jeans and sweater or top, ready to start your day, but you’re perplexed as to what shoes or boots to wear with your jeans. Can you relate?? It is actually one of the most common questions we get each fall. The confusion is easy to understand. We are no longer only wearing skinny jeans. Now…there are SO many different denim silhouettes that are on-trend: flared, crop-flare, cropped, wide-leg, straight-leg, and even joggers. But, I don’t want you to worry another minute because in this post…we’ve got you covered! Keep scrolling for a simple and complete breakdown…of exactly what shoes or boots to wear with your different types of jeans!

If you want even more tips on how to wear boots with jeans, make sure you check out this post next.

What Shoes To Wear with JeansWhat Shoes To Wear with Flare Jeans


What Shoes To Wear with Flare Jeans

Let’s begin with one of the simplest silhouettes…the flared jeans. I love to wear a pair of flattering flared jeans with some classic pointed-toe booties. But, the beautiful thing about flared jeans is… you can pretty much get away with wearing any shoes or booties because you don’t see much of them anyway…easy peasy! Simply pay attention to the hemline of the jeans in relation to the ground. Ideally, for maximum length, your jeans should be 1/2″ – 3/4″ inches off the ground.

In this look above, I’m wearing a pair of flared jeans by Mother. I have these jeans in a few washes, but I really love this classic denim wash called ‘Meet Cute’. The fit of Mother jeans is SO good. I love the high-rise because it smooths out the mid-section, and the flared leg is super elongating. Adding a pair of dark-toned, pointed-toe booties elongates my legs even more. I love this pair by Schutz. If you’re looking for a pair of basic, but sexy black booties, these are a wonderful option. They have a sexy stiletto heel that’s about 3.5”, a 5” shaft, and they also come in ivory. Schutz makes very chic and stylish shoes that are comfortable, high-quality, and affordable. With flared jeans, I would avoid any boots or booties that are super tall. The shaft will create bulk under your jeans.

turtleneck slit sweaterturtleneck slit sweater with jeans
Black Sweater

I paired the flared jeans with the coolest turtleneck sweater by ASTR the Label. I love the dramatic long length and slit. It’s a really modern sweater that’s easy to style with jeans for a unique look. The weight is also perfect for fall…not too warm but not too cool. Plus, it’s super affordable! I completed the look with some gorgeous new Monica Vinader pieces and a pair of chic, black square sunglasses to add some more drama. Like I always say…I like drama in my clothes, not my life! 😉

Keep scrolling for a game-changing graphic – so you never question what shoes to wear with your jeans again!

What Shoes To Wear With Different Jeans

What Shoes To Wear With Different Jeans

Please use the graphic above as a quick reference guide. You can also use the individual graphics below. During the winter months, you can add a water-resistant bootie where you see a similar style. And, during the warmer months, you can also add heeled and wedge sandals to all of these denim styles.

What Shoes To Wear With Skinny Jeans

What Shoes To Wear With Skinny Jeans

You can wear SO many shoes and boots with skinny jeans! When in doubt tuck the jeans into your booties or try a cuff (more details on how to cuff here). Other options include sneakers, combat boots, any-shaped-toe boots (almond, pointed, round, square), mid-calf boots, high-shaft boots, flats, mules, slingbacks, sandals, wedges, and pumps. I prefer booties with a slightly open or wider shaft so they seamlessly fit over the jeans.

what shoes and boots to wear with straight leg jeans

What Shoes To Wear With Straight-Leg Jeans

Straight-leg jeans have roomier leg openings so it’s easy to pair pretty much any kind of shoe with them too. But unlike skinny jeans, all you have to do is let the jeans hang over the boot or shoe…no tucking or cuffing is required. I wouldn’t wear knee-high boots because they likely won’t fit under your jeans, but sock booties and booties with a regular shaft width and height will work beautifully. More shoes you can wear with straight-leg jeans include sneakers, mules, loafers, sandals, wedges, pumps, flats, lug-sole boots, combat boots, sock booties, loafers, sock booties, and any-shaped-toe booties (almond, pointed, round, square). Again, remember, you don’t want to add bulk under the jeans so pay attention to the height and shaft of the boots.

What shoes and boots to wear with cropped jeans

What Shoes To Wear With Cropped Jeans

Another easy pair of jeans that you don’t have to think much about when it comes to shoe choices is…cropped jeans! I especially love cropped jeans with sock booties or with standout heels. More shoes to wear with cropped jeans include pumps, sandals, wedges, any-shaped-toe booties with a regular shaft, combat boots, mules, loafers, flats, sneakers, lug-sole boots, and sock booties. With your cropped jeans, you generally don’t want the top of your bootie to compete with the hemline of your jeans so pay attention to bootie height and bulk. (NOTE: I wouldn’t wear knee-high boots with this style.) Also, consider that this length really frames the shoe so either go with a similar toned shoe or boot to keep elongate the body or choose a statement shoe option. I didn’t show any statement shoes in the graphics, but they include any bold colors, sculptural details, embellishments, straps, etc.

What shoes and boots to wear with flared jeans

What Shoes To Wear with Flare Jeans

Since you won’t see much of the shoes underneath the longer flared jeans, you can wear pretty much any shoe style! The one exception is knee-high or over-the-knee boots. Those will create too much bulk under the jeans. More shoes to wear with flared jeans include sneakers, loafers, mules, sandals, wedges, pumps, flats, any-shaped-toe boots, combat boots, and sock booties. Remember, if you want your legs to look a mile long, your jean hemline should be 1/2″ to 3/4″ off the ground – almost dusting the ground!

what shoes and boots to wear with wide leg or baggy jeans

What Shoes To Wear With Wide-Leg Jeans

Similar to flare jeans…the same rules apply for wide-leg jeans or any sort of baggier, on-trend jeans styles. Shoes to wear with wide-leg jeans include sneakers, slingbacks, mules, sandals, wedges, pumps, flats, any-shaped-toe boots, combat boots, sock booties, and lug-sole booties. When I wear flared or wide leg jeans, I love to pair them with platform shoes or booties to add maximum height and length.

What shoes or boots to wear with jogger jeans

What Shoes To Wear With Jogger Jeans

We decided to throw this wildcard into the mix in case any of you are experimenting with some of the fun, trendy new denim styles. For jogger jeans, shoes that are more fitted to the ankle are best. It’s very trendy to tuck jogger jeans into knee-high boots right now so we included those for any of you who like to try something fashion-forward and exciting! I recently wore mine with some tall western boots and loved the look! More shoes to wear with jogger jeans include mid-calf boots, high-shaft boots, sneakers, slingbacks, any-shaped-toe style, combat boots, pumps, mules, flats, platform boots, and sock booties. Another trendy style this season are cargo jeans. Simply follow the graphics above to help with shoe choices.

If you have any more questions about what shoes you can wear with different jean styles, please let us know in the comments below!

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8 thoughts on “What Shoes or Boots To Wear with Your Jeans – A COMPLETE Guide!

  1. Thank for the information. I’ve recently discovered the 2.5 heel from poppy barley, but have struggled to know how to style the scalloped top of the bootie with skinnier type jeans.

    1. It can be tricky! We recommend you either choose an ankle length jean that hits just above the scalloped top of the bootie, or a longer straight-leg or wide leg jean that fits over the top of the bootie. If you are planning on wearing skinnies, just cuff the bottom a bit so the shoe details will show. Let us know if that works, Anne!! ~Team Busbee

  2. you explained the flare leg Jean so well and included how far from the ground the hem should hit. For straight leg jeans, it seems as though it should hit at/around your natural heel and it’s ok to show whatever heel height you have (as opposed to wide and flare where you want to hide the high heel to elongate legs). Would you agree?

    I’m five feet tall and I’m forever hemming my jeans (and some wide leg I have hemmed several lengths to match different heel heights) – so wondering if I need to go to these lengths to make my straight jeans perfect, or if 1 length will work with all shoe heights?

    1. You’re absolutely right! You can get away with showing a little more heel when wearing straight-leg jeans. Every pair of jeans and heels is different so you have to play around with it a bit. But you have more leeway when it comes to straight-leg jeans. Hope that’s helpful! Thanks so much for reading! ~Team Busbee

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