What Shoes To Wear With Straight Leg Jeans

As we slowly peel off our painted on skinny jeans and trade them in for more straight leg silhouettes, the number one question I get is what kinds of shoes can you wear with straight-leg jeans. And while the answer is truly, almost any shoe you probably already own, I think some visuals may help.

While most of your shoes from flats, to sneakers and heels will likely go just fine with your new straight leg jeans, there’s one type of shoe that is definitely more challenging. And it’s the one that I truly think is throwing us Millennials through a loop.

The bootie.

And I think the reason for this is because we are so used to owning a similar type of ankle bootie. And these styles do not, I repeat, do not work with straight-leg jeans.

When I think of all my ankle booties that just never worked with straight-leg jeans, they were all the styles that were designed to be worn with skinny jeans to show off the boot. So let’s dive into all the shoes you can wear with straight leg style jeans and a few outfit ideas to get you inspired.

What Shoes To Wear With Straight Leg Jeans

What Length Should My Straight Leg Denim Be?

Let’s get this one out of the way before we dive into the shoes. While the shoes are the #1 question, this seems to be a close second. I think this is 100% a preference. And many lengths can work with many styles of shoes.

I personally feel like a slight crop is best for me. Hitting at or right above the ankle. You can also have your jeans puddle to the floor like we’re back in high school. And these too would work with all these shoes. It’s just a matter of what YOU like.

I truly don’t believe there’s a better option. I think you just have to try on some jeans and decide what you like best on your body with the majority of your shoes. And I think if you want to wear heels, maybe you’ll want a longer inseam.

Or maybe you prefer a shorter inseam so that you can show off the shoes. It’s all about preference and the overall fit of the straight leg jeans you’re choosing.

Also, there are now many different styles of looser fitting jean. We’re trading in our skinnies for not just slim straight leg (those are my personal favorite and the easiest transition into this new trend) but also truly baggy wider leg jeans. These tips and shoe options work with all these styles.

Sneakers, Any Kind Of Sneaker

You can probably wear just about all your sneakers with your straight-leg denim. Definitely, chunkier sneakers are more on trend at the moment, but you can still wear your favorite Converse.

I really love a dad sneaker like these Adidas, or Madewell Trainers, and of course, my favorite platform Converse with my straight jean styles. This is usually what I’m wearing when running errands these days and feel put-together. And as you can see, any length of straight leg jeans works. Whether you want to show off your ankle and the entire shoe, or not, both work great!

Glove Or Sock Booties

There is a very specific type of boot that works with a straight leg jean, and it’s the glove or sock bootie. It’s just an ankle bootie that is a bit more fitted around the ankle, and goes up a bit higher than the ankle booties that we’re used to.

The ones we had for years were meant to be shown off with skinny jeans. They hit lower on the leg, usually weren’t skin tight to the ankle, and were intended to be shown off! These ankle boots are sleeker in my opinion and have a more modern and clean line look to them.

You can also see in my roundup below of boot options, that there are still plenty of styles to choose from. You can do a chunky flat lug sole, your favorite combat boots, sleek kitten heels, or a fun and sexy high heel pointed toe boot.

The key is simply to look for boots that lay close to the body and go up a bit higher in terms of shaft height. This blog post on how to style boots with straight leg jeans has tons of ideas and outfits too.

Loafers And Ballet Flats

The perfect shoe to pair with your denim are a pair of loafers or the ballet flat which is having a major comeback. This adds a really preppy touch your denim and work nicely with a sweater or blazer. Lug sole loafers are also on trend, but you can go with a classic pair too.

how to style loafers for fall

Flat Sandals Or Heeled Sandals

For spring and summer, a sandal was my go-to for pairing with my straight leg denim. Any easy leather slide, or a flip-flop, all worked nicely. And you can even do a low heel sandal as well for something a little dressier!

Mules, Clogs And Birkenstock Boston Clogs

Yes, you heard me, Birkenstock Boston clogs. They’re back. But no matter what type of mule or clog you want to wear that fits your personal style, they actually pair really well with straight-leg jeans. You can go cropped or longer hemline too here. It’s all a preference. For me and my fall wardrobe, I’m trying these clogs for a more 70s vibe.

Pumps And Heels

When it comes to dressing up your straight leg jeans for business casual looks, date night outfits, or heading out with friends for drinks, add a heel! Any and all types of pumps and heels can work. This is also when I think a longer inseam works well with heels like Brooklyn Blonde did here.

You can even go longer and let the jeans hit the floor if you want. I really love that combination and am personally looking for a good pair of longer straight leg jeans to wear with all my high heels for fall. I think a relaxed 90’s style straight leg jeans is perfect with heels.

As you can see, so many shoes pair with straight leg jeans. From your favorite flats and sneakers, to heels and sandals. And when it comes to pairing a bootie with your straight leg jeans, it’s best to aim for a boot that has a higher shaft and is more snug to the leg.

My general rule of thumb when pairing booties with straight leg jeans is to choose the jeans that have a slightly wider leg opening to allow them to fall nicely over the boot.

Now that you can see how easy it is to pair your straight leg jeans with the majority of your shoes, let’s get to styling your favorite straight leg jeans!