what shoes to wear with jeans

The Best Shoes to Wear with Different Types of Jeans

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Any day of the year, jeans are my top choice for what to wear out of the house. And these days we have a lot of options about the style of jeans we wear. From straight-leg to bootcut, flare, mom jeans, and wide-leg blue jeans. And even the hotly debated, skinny jeans.

When it comes to pairing the right shoes with your favorite pair of denim, things can get a little tricky. Don’t worry though, I’m here to be your style guide as you navigate the world of jeans and shoe combinations.

In this post, I’ll show you 6 of the most popular jean styles paired with 6 different styles of shoes. You’ll see straight leg, kick crop, wide leg, flare, bootcut, and skinny jeans. I’m showing you outfits using the same 6 pairs of shoes, so you can see the best shoes and also see shoes that don’t work and my thoughts about each. Plus I have a few additional pictures of shoe and jean combinations that are a total home run. I also include links to shop the jeans and shoes.

Ready to dive in? First up, straight-leg jeans.  

Shoes with straight-leg jeans

Straight-leg jeans are fitted in the hips and thighs and then fall straight from the knee to the ankle. Many styles will call themselves straight jeans when they aren’t, making it harder to pair them with shoes. To see if you have true straight jeans, fold the hem up to the knee. If the hem is the same width as the knee then they are true straight leg jeans. 

Straight-leg jeans are the most classic and timeless style of jeans. The hem tends to hit right at the ankle. I’m 5’6” and a 28” inseam is the perfect ankle length for me. They create a silhouette similar to the cute ankle pants Audrey Hepburn wore. Which is a look I’ve always loved. They’re also a fresh alternative to skinny jeans. 

Classic straight leg jeans are a great choice if you want to pair them with a variety of classic and modern styles of shoes.

Let’s take a look at some jeans and shoes combinations. 

  1. Chunky loafers. Given the ankle length of these jeans and a slightly wider hem, these more modern and trendy patent leather chunky loafers definitely work here. More classic penny loafers would work too. Be careful with platform loafers with a very chunky high heel as they may make your feet look like concrete blocks in comparison to slim legs. 
  2. Cap-toe ballet flats. Chanel-inspired cap-toe flats are another great option with straight jeans. The ankle length perfectly shows off the shoes and they don’t get lost in a long jeans hem. 
  3. Classic ankle boots. When you match your ankle boots to your skin tone, it lengthens the look of the legs. I’d like this look even better if the jeans were shorter and you could see the entire ankle of the boot like you can with the next pair of jeans.
  4. Chelsea boots. I love these flat chunky sole Chelsea boots with straight jeans. The hem falls straight down over the shaft of the boot maintaining the long leg of the hem.
  5. Black Adidas tennis shoes. These slim Adidas tennis shoes are a great match for these slim-fitting jeans. The jean legs look nice and long and the sneakers are proportionate to the jeans. I love wearing sneakers with jeans for a casual look. 
  6. Clogs. These 2-inch heel clogs aren’t too bulky and add a little height to this look. They show off the flattering inside of the ankle and match the proportions of the jean hem.

If you struggle to find ankle boots that work with your straight jeans, try sock boots. Sock boots have a shaft made of stretchy material that hugs the ankle and fits easily up under the hem of these jeans.

Shoes with kick crop jeans

Kick crop jeans have been gaining in popularity. I personally love them in the warmer months and colder weather! They are cropped and hit an inch or two above the ankle. These kick crop jeans from the Gap have a 26.25-inch inseam.  They have a slight flare from the knee to the hem. As someone who is larger on the bottom, the wider hem helps to balance the proportions of wider hips. I’m 5’6″ and have a size 12 rear and love the balance they provide. I love them so much, I also own them in a longer 28″ length.

Many people are worried that the cropped length makes the legs look shorter. If you choose a pair with a higher waist rise, you gain an inch or two at the waist that offsets the length you lose at the ankles. 

The kick crop flare is a fun and fresh take on straight jeans. I also find them really easy to pair with a ton of different shoe styles. Shorter jeans really show off your shoes.  

One note of caution, if you don’t love showing your ankles, you may not love this style of jeans. 

Let’s look at these jeans with different styles of shoes.

  1. Chunky loafers. Chunky loafers are a perfect match with these wider hem jeans. Showing a little ankle with a wider hem creates a smart look and draws attention to these fun patent leather loafers. 
  2. Cap-toe ballet flats. If you want to show off your classic-style ballet flats, this is the perfect way to do it. 
  3. Clogs. This is another winning look for a Boho, laid-back feel. These slim clogs show off the ankle and add a little height. 
  4. Classic tan ankle boots. I love these ankle boots with kick crop jeans even more than with the straight jeans we saw in the last look. The hem of the jeans hits right at the top of the ankle of the boot. Showing the full ankle of the boot shows off the slimmest and most flattering part of the boot.
  5. Chelsea boots. This is another winning pairing. The hem of the jeans slips right down over the top of the boots showing off the ankle of the boot. The lug soles aren’t so chunky so they don’t create a block-heavy look in the opening of the hem of the jeans.  
  6. Black Adidas tennis shoes. These jeans are the perfect length to show off your sleek sneakers and create a relaxed look. White sneakers would also be great here.

Since these jeans are so great at showing off your shoes, they’re also the perfect choice with ankle wrap flat sandals in the summer.


Next up, let’s look at longer jeans with shoes, starting with flare jeans.

Shoes with flare jeans

Flare jeans are fitted in the hips and thighs, often have a high waist, and come to the floor or just above it. The hem kicks out in a flare from the knee to the floor. Again, if you’re larger on the bottom like I am, the flare helps to balance out wider hips. 

Choosing shoes with flares gets a little trickier. Let’s take a look.

  1. Classic ankle boots. Shoes with heels really let your flare jeans shine. The drama of wearing flare jeans comes from the hem of the flare falling straight to the floor with an inch or two of space between the floor and the hem for a leg-lengthening effect. Block heel ankle boots of any height are a great option with your flare jeans. These would be even better with a taller heel. 
  2. Clogs. This isn’t bad. These clogs have a platform and lower heel than the last look but still offer some height. The hem of the jeans breaks or folds slightly indicating a slightly higher heel would be better. Platforms are great options for adding comfy height with flares. 
  3. Chelsea boots. You may be surprised that I actually like Chelsea boots with flare jeans. Why? The lug sole adds height. And also the toe box is long and flat so they have some presence under the flared hem. But the hem of the jeans does pool a bit on the top of the shoe.
  4. Chunky loafers. These chunky loafers get a little lost under the hem of these jeans. The material pools at the hemline. They have a hard time competing with the width of the flare of the hem.
  5. Cap-toe ballet flats. Because these ballet flats are so flat, the hem of the jeans bunch and pool so the flare doesn’t get a chance to fall gracefully and create legs for days. If your jeans are shorter or have a narrower flare, this may work. Also, pointy-toe flats are a good option to try with shorter flare jeans. A pointy toe extends the leg line. 
  6. Black Adidas tennis shoes. I love creating a sporty chic moment by wearing Adidas and long jeans. But this creates a lot of pooling at the ankles and I wouldn’t be comfortable wearing this look out of the house. If I hemmed the jeans, I would totally wear this.

These 3-inch stacked heel knee-high boots are my new favorite way to wear flare jeans. They’re gorgeous with them.

Stacked heel boots with flare jeans

Pointy toe ankle boots are another great option since they extend the leg line.

Shoes with bootcut jeans

Bootcut jeans are universally flattering thanks to their slight flare at the bottom. They’re ideal for pairing with a variety of shoe styles since the flare isn’t as wide as with flare jeans. I purposely bought mine in a shorter 30-inch length because I wanted to easily wear them with flat shoes. 

Let’s explore the different shoe options and how they work with bootcut jeans.

  1. Cap-toe ballet flats. I love ballet flats with bootcut jeans. The hem of the jeans falls straight down without any pooling or bunching. And they’re super comfortable to wear. 
  2. Black Adidas tennis shoes. Here’s another look that I love. The flare of the hem doesn’t overwhelm and bunch or pool and you can see a good amount of the sporty cuteness of these sneakers. 
  3. Chunky loafers. I don’t love these black patent leather loafers with these bootcuts. Because of the narrower hemline, so much of the black shoes show that the black stops the leg line and they look out of place here. I’d pass on this look. 
  4. Clogs. This is another look that works with them. The modest heel and slim clog give a Boho look. A Boho blouse would be the perfect top with these clogs.  
  5. Chelsea boots. The rise of the foot box of these Chelsea boots is nice and flat, creating the appearance of a longer toe box. This is a look that works.
  6. Classic ankle boots. When you match your shoes to your skin tone, it lengthens the leg line. And these ankle boots do that with these bootcuts. I’d like this look even more wearing bootcut jeans that are 2 inches longer so the jeans drape over the toe box.

Shoes with wide leg jeans

Wide-leg jeans are relaxed in the hips and thighs and all the way down to the hemline. You get to decide if you prefer your wide-leg jeans with heels so they fall straight down hitting right above the floor, or if you’ll let them pool at the top of the shoes. Embracing the volume and letting them pool creates a relaxed, laid-back look.

  1. Chelsea boots. Chunky boots are a great option with wide-leg jeans. They add a cool element and the chunkiness balances the width of the hem. They stand up to the volume of the wide hemline.  
  2. Classic ankle boots. Ankle boots with a heel are another great option. These tan boots just peek out from under the hemline creating the look of legs for days. 
  3. Clogs. While these platform clogs have a slim appearance, they hold up to the wide leg because of the platform and the heel. This works.  
  4. Black Adidas tennis shoes. Wide-leg jeans create a cool and casual outfit with these Adidas sneakers. The white sole contrasting with the black sneaker grounds the look and draws in the eye. They pool down around the foot and create a sporty fresh vibe. 
  5. Black loafers. Loafers are all the rage these days. And chunkier loafers work with wide leg jeans since they have some presence in the hemline.
  6. Cap-toe ballet flats. These ballet flats aren’t my first pick with these jeans. Since they’re flat and have a narrow silhouette they get lost in this outfit and rather than looking laid back, they look like they’re drowning. If you’re going for a shoe with a narrow silhouette, try one with a heel (see the clogs or ankle boots).


Last but not least, skinny jeans. 

Shoes with skinny jeans

Skinny jeans have been at the center of controversy these days. One moment they’re in and then they’re out. As I mentioned in this Instagram post, at the end of the pandemic, skinny jeans were gathering dust in many closets because they were so tight at the ankles. And a ton of other jean styles came on the scene. But for some people, skinny jeans are still the style of choice if you don’t want your frame to be overwhelmed by fabric. 

Let’s look at shoe options with skinny jeans.

  1. Chunky loafers. Skinny jeans end around the ankle and since they fit slim, it’s common to wear them with an oversized blazer, sweater, or top to balance the slimness on the bottom. Here these chunky loafers work because I’m wearing a long double-breasted blazer. The chunky soles balance the blazer. 
  2. Cap-toe ballet flats. This is another look I can get behind. The shoes have a slim silhouette that works with the slim legs of the jeans. And the black toe ties in with the blazer. 
  3. Clogs. These are okay here. I’m not over the moon about them. The brown front of the clog looks heavy and a bit clunky as compared to the slim ankle and jeans. It may also be that I wouldn’t normally pair this blazer with these clogs. There’s nothing that really ties them into the look. 
  4. Black Adidas tennis shoes. I’m totally biased about my Adidas and love combining sporty slim sneakers with this long double-breasted blazer. The legs look nice and long in these skinny jeans.
  5. Classic ankle boots. This look is a miss for me. I folded under the skinny jeans so they hit the top of the ankle boots. And that makes the legs look shorter. This combination makes me think of elf shoes with tight leggings and curvy boots. Booties that reveal the ankle are a better match with skinny jeans.
  6. Chelsea boots. I rolled under the hem of the jeans for this look too. And it’s another one I’m not super fond of. With Chelsea boots, I prefer a pair of jeans with a wider hemline so they come down over the top of the boot and the leg line stays longer. Booties with a low shaft are a better match with skinny jeans. 

Booties with a low shaft stop around your ankle and hit below the hem of the skinny jeans.

While skinny jeans have taken a back seat to so many other styles of jeans, they’re still the perfect match for knee-high boots. So definitely don’t get rid of them. Just make sure they fit over the top of your jeans without any bunching. 

There are a ton of different shoe options to play with when you’re choosing shoes to wear with jeans. Play with it and find the combination that feels most like you and matches your personal style. 

Hi, Friend. I'm Marya. I'm so glad you're here!

I’m here to help women feel good inside and out through approachable everyday style inspiration and encouragement for midlife. Once upon a time, I worked as a therapist and coach. Now, I’m a holistic style blogger studying style coaching! Be So You celebrates leaning into who we were meant to be! 

Read about my  journey to self-discovery at 40. Follow me on Instagram here and Pinterest here. Send me a quick question through my contact page here.  

Fit Note: I’m midsized at 5’6″, 160 pounds, with size 12 jeans.

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