We are back with the third and final post in our denim series for this fall! So far we’ve talked about 5 Types of Jeans to Wear This Fall to help you decide styles to try given the shift in popular cuts, and I shared 5 Tips for How to Transition From Skinny Jeans to Other Cuts. Today we are talking about how to wear shoes with jeans in different cuts!
A lot can be said about how to pair shoes with jeans, especially when you consider all of the different cuts of jeans out there and all of the different types of shoes. Instead of jumping into a list of specific shoes to pair with specific types of jeans, I want to back up and share some foundational style principles that will help you figure out how to pair shoes with jeans more seamlessly. Knowing a few basic style principles helps you understand the WHY behind everything, which then helps you better troubleshoot on your own why certain pairs of shoes do or don’t work with certain pairs of jeans. So, that’s what we’re focusing on today.
But that said, if you would like further help with specific jeans and shoes combos, jump into the PMT Style Club! It’s such a great place to get your specific questions answered. Plus, you’ll have immediate access to a video lesson that provides more in-depth guidance on How to Pair Shoes + Pants and lists out different types of shoes you can wear with different cuts of pants, including picture examples. More importantly, with the Style Club you’ll have a place to try out all of your jeans-and-shoes combos and get advice from a knowledgeable community that can help with your specific questions. (And, it’s always fun to have a place to share that outfit that made you feel good!)
All right, let’s talk through some fundamental style principles that will help you figure out how to pair shoes with jeans in all those different cuts!
1. Make sure your jeans hit at the right length.
You might recognize this from 5 Tips to Transition From Skinny Jeans to Other Denim Styles. It is sooooo underemphasized but SO CRUCIAL for making jeans look good! You MUST start here, ensuring that your jeans are at the right length, no matter what cut they are!
The main goal for the length of your jeans is to maintain a long, clean leg line, aka eliminate bunching and pooling at the bottom, unless that is a completely intentional look you are going for. Otherwise, aim for the length of your jeans to maintain a clean leg line and look more polished. Plus, starting with these lengths helps immensely with shoe pairings.
The Ankle Length Sweet Spot – Where Ankle Length Jeans Should Hit
As a reminder, for ankle length pants, generally the sweet spot is for them to hit right at the top of your ankle bone to within an inch above, like in the picture above.
This guideline applies to every style of jeans you want to wear at ankle length. Your skinny jeans, slim straight jeans, straight leg jeans, wide leg jeans, crop bootcut jeans, girlfriend jeans. If you’re wearing it at ankle length, aim for this sweet spot.
Where Full Length Jeans Should Hit
For jeans at full length, aim for them to hit right at the top of your instep, not pooling or bunching with shoes on. This applies to non-skinny jeans like straight leg and wide leg cuts at full length. (Have skinnies hit at the ankle-length sweet spot mentioned above!)
Bootcut jeans can be a little longer as it’s recommended to wear them with a heel. Typically you want bootcuts to hit about 1/4″ to 1/2″ off the ground. However, you can fudge that a bit depending on the pair.
Both of these lengths are great starting points that will provide a solid foundation for figuring out shoes!
2. Sneakers – Aim for sneakers with a low profile.
Who says you can’t wear sneakers? Sneakers are more popular and more stylish than ever, but you have to start with the right kind. Low profile sneakers are the best choice for stylish casual outfits. (Opt for this type of sneaker instead of clunky and bulky trainers when it comes to wearing stylish casual outfits with jeans.) Low profile sneakers also go with the majority of denim cuts, whereas sneakers with higher shafts might require you to be more particular with the specific jeans you can pair them with.
Here are two examples of low profile sneakers. The first is a pair of slip-on sneakers. They have a classic and timeless style that goes with nearly everything. Notice how they have a low profile, keeping the ankle area uncluttered, which helps elongate your leg line.
The second pair has laces (though they are meant to be slipped on). And even still, the profile is low and keeps the ankle uncluttered.
Whether a slip-on style or a style with laces, a low profile sneaker works seamlessly with ankle length jeans of ALL cuts. Above I’m wearing them with crop bootcut jeans and girlfriend jeans. The key is that the LENGTH of your jeans hits the sweet spot! Sometimes some of the women we coach wonder why their outfits still look frumpy, and often their jeans are just a tad too long. Make sure your jeans are at the sweet spot, and it can make ALL THE DIFFERENCE!
Bonus Tip: Besides the lower profile, another thing I look for is a low vamp (i.e., the top portion of the shoe). I prefer when the vamp doesn’t come up all the way to my ankle, like you can see with the slip-on pair. I have rounder calves and relatively narrow ankles, and if the vamp is too high, it often cuts off my leg line and makes my legs look shorter and a bit stumpy. If you ever have this issue, then look for shoes with a lower vamp as well. 
Pictured borrowed from How to Wear Booties With Different Cuts of Jeans
3. Choose boots with a high enough and narrow enough shaft to fit under your jeans without bunching up.
Again, this is about keeping the leg line streamlined. With skinny jeans, you may have opted for boots with a lower shaft so you could cuff your jeans and show some of your ankle. That shoe style does not work quite as well with other cuts. (Aggghhh isn’t changing denim styles annoying? 😭)
For straight leg, crop bootcut, full length bootcut, and wide leg jeans, a couple of things to look for when it comes to ankle boots is finding a pair with 1) a narrow enough shaft that allows them to fit under your jeans and stay there, and 2) a high enough shaft that allows them to be covered by your jeans and not come out as you walk, so you don’t have to fix them all day. These guidelines apply whether we’re talking about ankle-length jeans or full-length jeans. If your jeans are ankle-length, the shaft would need to be even higher to compensate for a higher hem.
Bonus Tip: Out of all those denim cuts I just mentioned, I would choose slim straight leg cuts as the first type I test with when considering purchasing a new pair of boots. Out of the denim styles we have been talking about, slim straight jeans have the narrowest leg opening, so they need the narrowest shaft of boots. If the boots are slim enough to fit under your slimmest pair of jeans, they will most likely fit under the cuts with wider leg openings like bootcuts and wide leg jeans.
If a pair of shoes you want to buy doesn’t fit under your slim straight leg jeans, it doesn’t mean you shouldn’t keep them. Instead, make sure they work with at least two other pairs of jeans you own, whether other straight leg cuts, bootcuts, or wide leg jeans.
For more help with pairing booties and jeans, check out How to Wear Booties With Different Cuts of Jeans.
4. Go for shoes with an elongated toe box.
Do you ever pay attention to the toe box? You definitely should! Some toe boxes are longer while others are shorter, and the longer ones elongate your leg line while the shorter ones can make your leg line look stunted.
This applies to shoes in ALL styles, from sandals to flats to sneakers to boots and whatever else. And, it applies to all TOE styles, whether rounded, almond, pointed, square, or whatever. For example, some sneakers have a more squat toe box while others have a more elongated toe box.
Elongated toe boxes visually lengthen your leg line, and that helps create an overall more polished (and less frumpy) look. So, no matter what style of shoe you are going for and no matter if you’re talking about round toes or pointed toes, looking for something with an elongated toe box will help your outfits with jeans and sneakers look better!
Doing these things will help tremendously with all of the different shoe and jeans pairings so you can better pair shoes with jeans no matter what cut of jeans you’re trying!
Join us for Denim School!
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Learn how to pull off the different cuts of jeans based on your body type and get answers to all of your specific questions, like “What shoes can I wear with these jeans that I just bought?” and “Which brand of denim is good for pear shapes?” and more!
Learn more and join us inside the PMT Style Club HERE!
