What Shoes to Wear with Straight Leg Jeans – Both Cropped and Full Length

Some of my all time most popular blog post are about what shoes to wear with what jeans and how. How to wear ankle boots with jeans and how to wear ankle boots with straight leg jeans being the top two. Today I’m sharing all the tips and tricks on what shoes to wear with straight leg jeans including some do’s and don’ts on what makes things work well. These are just my personal preferences based on trial and error. If you like it, wear it! There are no hard and fast rules in fashion.

Jean Tips

Before we dig into shoes, I want to share a little bit about my jeans here. When picking a cropped straight leg jean, I recommend looking for one that hits just above your ankle bone at the narrowest part of your ankle/leg. This is often longer than you would imagine. You want to avoid it hitting higher up on your calf at the wider area. This is for several reasons. First, it will flatter your leg more. Second, it gives more shoe options. As my photo below shows, it allows for ankle boots to more easily tuck under and just overall looks better.

My all time favorite cropped straight leg jeans are my Levi’s Ribcage ankle straight jeans. I buy them off the Levi’s website where they are available in different inseam options. I am 5’10 and wear the 29 inch inseam. They come in so many great wash options. I am wearing the Jazz Pop color here. I also own the black one and love it!

As for a full length straight leg jean, my current favorite are the Madewell 90s straight leg pair. I am wearing the long in my usual Madewell size which is one down from other places. I would recommend getting a full length pair with enough length to have a slight bend in the leg at the bottom. This will allow for enough room for heels while not being too long for sneakers.

What Shoes to Wear with Straight Leg Jeans

Sleek Leather Boots

A great pair of sleek leather boots, whether kitten heel or higher, are a great option for either a cropped or full length pair of straight leg jeans. Something about the sleek leather look of it pairs seamlessly with both jeans. Style with a simple sweater or blouse for an easy everyday outfit. Shop my boots here and use code AMYANN20 for a discount!

• DO pair your straight leg crop jeans with a sleek leather boot
• DO pair your full length straight leg jeans with a sleek leather boot

Short Suede Boot

A shorter heel suede boot can be a little trickier. While I think these work perfectly well with a cropped jean, I do not think they look great with a full length straight leg jean. The added jean length lends to bulk over the boot. Paired with the almost always bulky heel just ends up with a look that feels kind of lacking. I would avoid this combo. I do wear my cropped jeans and boots all the time though!!

• DO wear your cropped straight leg jeans and short suede boots
• DO NOT wear your full length straight leg jeans and short suede boots

Sneakers

Sneakers are without a doubt my most work shoe! As a mom, I just love reaching for a fun sneaker and jean outfit combo. Good news – sneakers work perfectly with everything! Pair them with all your favorite jeans. Hooray! Shop my sweatshirt here.

• DO pair your straight leg crop jeans with a sneaker
• DO pair your full length straight leg jeans with a sneaker

Mule, Loafer, or Flat

Similar to a sneaker, a mule, loafer, or fun flat is my go-to shoe during the spring, summer, and early fall when I am wearing anything that is dressier than what a t-shirt requires. If you work in an office that is jean friendly, these make an ideal shoe too! Both of these work with a cropped or full length straight leg jean as well and look equally polished! Shop my mules and my favorite blazer here.

• DO pair your straight leg crop jeans with mules, loafers, or flats
• DO pair your full length straight leg jeans with a mules, loafers, or flats