The Best Shoes To Wear With Straight Leg Jeans

Straight leg jeans entered the fashion scene a few years ago after a relatively long hiatus during the skinny jean reign. At first, we weren’t exactly sure what to think about this style of jean. But what we can now say is…. YES YES YES! We are fully converted over to the straight leg jean trend and really loving it. There are so many fun ways to style this type of jean. Not to mention, they are quite comfortable! One of the biggest questions we get from clients is… What are the best shoes to wear with straight leg jeans? Well, ladies ~ keep reading!

As we have this conversation today, keep in mind that with fashion and style, there are admittedly “rules”…. But they aren’t actually hard and fast rules. We think of them more like a roadmap of guidelines to help us to of course look our best… But also to help us to figure out our own individual preferences and styles. And so, we will go through some tips and tricks that we tend to lean on as we are styling our straight leg jeans. But remember that you are always free to the best thing, which is to just do you!

The Best Shoes To Wear With Straight Leg Jeans

There are so many types of shoes that work well with straight leg jeans… Chelsea boots, mules, loafers, ballet flats, ankle strap sandals, dressy sandals, sneakers… If we covered all of these shoes here in this blog post, we would end up writing a small novel! So instead, we are going to focus on a few key categories. For style inspiration for the ones we don’t cover, refer to our photo gallery at the bottom of the blog! And one more little note… If you see a shoe silhouette you like here, be sure to check the link, as most of these pairs of shoes have various color and texture options. We started to list them all in the post, but it became cumbersome and hard to follow! So, let’s take a look at the best shoes to wear with straight leg jeans!

Let’s tackle the more “complicated” shoe category first. We love a good Chelsea boot in general, and especially with straight leg jeans. Not only do we love the look, but we also find Chelsea boots and straight leg jeans to be a very functional elevated casual look for everyday, busy life. Especially for those cold and rainy days we are all dreading!

How To Wear Chelsea Boots With Straight Leg Jeans

For starters, leave a small gap between the bottom of your straight leg jeans and the top of your Chelsea boots. What happens in that gap is up to you… Skin, socks, and fishnet stockings are all good! Consider keeping those cropped jeans out for fall and winter! If needed, cuff your jeans to achieve the proper gap (yes, cuffing is back!). As far as the cuff is concerned, we prefer a medium sized cuff, 1-2 inches or so. However, we are seeing all kinds of differing cuffs – really narrow, really wide… It seems like anything goes!

Remember how we said that fashion rules aren’t really rules at all? Note that you can of course still wear your hemline over the top of the boot – it might just be a little less flattering depending on your height and leg length. But it isn’t a total NO either!

Secondly, choose ankle hugging boots. You don’t want the shaft of your boot standing too far away from your leg. You want the narrow area of your ankle to be accentuated by the boot.

Some Of Our Favorite Chelsea Boots

Lucky for us all, Chelsea boots are on trend this fall! You can get almost any style of Chelsea boot you can imagine – lug sole, block heel, waterproof, suede, leather, rain…. SO many adorable options. We pulled a few of our current favorites for you guys below.

Black Grain Leather Flat Sole Chelsea Boot | Brown Waterproof Low Block Heel Chelsea Boot | Black Leather Low Block Heel Chelsea Boot | Taupe Waterproof Chunky Platform Chelsea Boot | Black Buckle Strap Chelsea Boot | Black Stitch Detail Rain Chelsea Boot | Honey Leather Wooden Block Heel Chelsea Boot | Black Leather Low Lug Sole Chelsea Boot | Cognac Leather & Knit Heeled Lug Sole Chelsea Boot

Loafers And Straight Leg Jeans

We recently did a deep dive into the loafer trend in our recent blog post on the resurgence of so many beloved 90s styles. When it comes to wearing loafers with straight leg jeans, the conversation becomes more simple. You want your jeans to sit above the highest part of your loafer. Showing your ankle bone is another good parameter to think about. It’s easy to remember if you think of it this way…. Wear your jeans at a length that shows off your loafer rather than hides it. We don’t necessarily recommend cuffing your jeans with loafers (although the exception in some cases would be for a heeled loafer mule)… So choose a pair of jeans that naturally sits at the right length. Here are the loafers we shared in that blog post – SO.MANY.GOOD.ONES!

How To Style Mules And Ballet Flats With Straight Leg Jeans

Same idea for mules and straight leg jeans… Keep that jean hemline off of the shoe and show a little skin around the foot and ankle.

Ballet flats are also resurfacing! Our tip for wearing a ballet flat with straight leg jeans? Offset the sweetness of the ballet flat with something more edgy or trendy, such as choosing straight leg jeans that are distressed, or pairing an oversized sweater or leather moto jacket with your straight leg jeans.