Fall/Winter Fashion
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What Shoes to Wear with All Types of Jeans

After writing several posts about the best denim and shoe combinations for fall, today I’m summing up what shoes to wear with all types of jeans. I even created an infographic of sorts to make it easy to reference.

What Shoes to Wear with All Types of Jeans Women 2022CLICK TO SHOP!

If you’ve been struggling with what shoes to wear with all types of jeans this fall, this should help! It isn’t an exhaustive list of denim and shoe pairings, but it’s a good place to start.

What Shoes to Wear With Straight Leg Jeans

Frame Le High Straight // Franco Sarto Bridget Mules

Straight-leg jeans come in lots of variations, from relaxed and slouchy to sleek and slim-fit; and they can be cropped, ankle length, or full length.

Cropped and ankle length styles have been trending for the past few seasons, but full length styles and more relaxed fits are hitting the mainstream this year. First let’s talk about what shoes to wear with straight crop and straight ankle jeans.

Straight Crop & Straight Ankle Jeans

Crop straight and straight ankle jeans look great with retro fashion sneakers, classic or lug sole loafers and loafer mules, block heel mules, clogs, and ankle boots. It’s hard to find a shoe they don’t work with, but ankle boots can be a bit tricky.

What Shoes to Wear with Straight Ankle JeansFrame Le High Straight Ankle Jeans // Aquatalia Brigitte Luxe Bootie // rag & bone Retro Sneakers // Jeffrey Campbell Velviteen Bit Loafer

The key with pairing straight leg jeans and ankle boots is finding the right combination of denim length and width, and boot shaft height and width. You either want the jeans slide easily over the boots, or end right above the boot shaft so that you expose an inch of skin (or sock). If they’re too close, they will get hung up on the top of the boot and look janky.

HINT: A slim boot shaft works best when wearing the boots under the jeans. You can read more in my post, How to Wear Ankle Boots with Straight Leg Jeans.

Full Length Straight Leg Jeans

In my opinion, full length straight leg jeans look best with a bit of a heel, especially the more relaxed styles. They look really good with heeled ankle boots and clogs, and even a more delicate sandal during the warmer months.

What Shoes to Wear with Straight Leg Jeans AGOLDE Lana Vintage Straight Jeans // Sam Edelman Western Boots // Korks Arielle D’Orsay Clog // rag & bone Retro Sneakers

Relaxed, full length straight leg jeans with retro running sneakers is on trend at the moment, but it’s my opinion that ladies of a certain age run the risk of looking frumpy in that combo. The whole outfit must be styled in a current way to avoid looking frumpy or stuck in a rut, so that’s a look I’m steering clear of for now. Of course, that is subject to change at any time!

Okay, moving on to bootcuts and flares!

What Shoes to Wear with Bootcut & Flare Jeans

AG Farrah Bootcut // Marc Fisher Pointed Toe Bootie

Bootcut jeans and flares are pretty much interchangeable when it comes to shoe pairings, so I’ve lumped them together for the purposes of this post. Like straight leg jeans, bootcuts and flares come in crop, ankle, and full length styles. Let’s start with cropped and ankle length flares.

Demi Boot & Crop Flares

Cropped and ankle length bootcut jeans and flares are great for showing off your shoes and the slimmest part of the leg. Sometimes you will see these called demi boot or crop bootcut or kick crop jeans.

How to Wear Crop Flares for Fall Paige Claudine Ankle Flare // Paige Pointed Toe Bootie // Veja Esplar Sneaker // Steve Madden Pointed Toe Mule

When it comes to ankle length and crop flares, ankle boots are a great option, but you have to play around with the combination of inseam length and shaft height. Just like with straight crops, you don’t want your jeans getting hung up on the back of the boot.

Crop flares also look great with block heel mules, loafer mules, and all types of fashion sneakers. And clogs almost always work. These pairings look best when they allow some ankle to show.

Full Length Flares

Full length flares and bootcut jeans look best with a heel or a platform sole, and even better with a pointed toe heel. And clogs are a great option for a more casual vibe; plus they’re a big trend right now, which keeps your bootcut jeans looking more 2022 than 2002.

How to Wear Bootcut Jeans this Fall 2022 AG Farrah Bootcut // Michael Kors Slingback Heels // Mother Raw Hem Flares // Kork-Ease Darby Clogs // AG Farrah Bootcut // Marc Fisher Pointed Toe Bootie

If you decide to wear full length flares with flats, a pointy toe will look best. And no matter which style of shoe you choose to wear, be sure the jeans are hemmed or cut so they don’t drag on the floor.

I recommend avoiding sneakers and loafers with this style of jean, but do whatever makes you feel comfortable and confident!

What Shoes to Wear with Wide Leg Jeans

What Shoes to Wear with Wide Leg Pants Spanx Wide Leg Pants // Seychelles Wood Heels

Wide leg jeans can be tricky to style, but they generally work best with a heel or platform. Or chunky loafers and platform sneakers look great with them too. Basically, you want a chunkier style of shoe to balance this bold silhouette.

And finally, if we’re going to talk about what shoes to wear with all types of jeans, we can’t leave out the good old skinnies!

What Shoes to Wear With Skinny Jeans

AG Farrah Ankle Skinny Jeans // Marc Fisher Yale Chelsea Boot

While skinny jeans are on the downward slope of the trend cycle, you’ll still find them in stores because many women are still wearing them. If you love your skinnies, be sure to pair them with current tops and shoes to avoid looking dated.

In my opinion, skinny jeans look best (and more importantly, most current) with a lug sole Chelsea boot, retro sneakers, clogs, or chunky loafers… basically anything that is current and on trend. Also, a chunky profile will help balance the narrow silhouette.

Are Skinny Jeans Still In Style for Fall 2022? AG Farrah Ankle Skinny jeans // Kork-Ease Darby Clogs // rag & bone Retro Sneakers // Sam Edelman Christy Loafer

I would steer clear of ballet flats, pumps, low split shaft booties, peep toe booties, and slim Converse. Even though those combinations work, they’re almost guaranteed to look dated because that’s how we wore them for so long.

In Summary

At the end of the day, you have to play around in your closet and try on different combinations to see what works best for you, but hopefully this helps you narrow down your options.

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And if you want more info, see all my posts about 2022 Fall Trends!

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45 thoughts on “What Shoes to Wear with All Types of Jeans

  1. Jolynne, seriously you really the BEST! All time favorite post, well, actually this and the white t shirt/ jeans post.

  2. Wow!!! I’m working at the moment and haven’t even had a chance to read through this but I can already tell I’m going to need to print this graphic and have at the ready! Great post!!

  3. I love, love, love the infographic! I have enjoyed all of your posts about jean/shoe pairings. Such a big help, thank you!

  4. LOVE the graphic. Easy to screenshot and keep it with you on your phone for reference when you’re out shopping.

    Enjoy your night out with girlfriends and I hope Becca has a happy birthday!

  5. Great job on this post. The graphic is going to be used by many. Happy B’day to Becca. Is she 17? Have fun tonight with girl friends.

  6. PS The key really is to just try pairings in our own closet, as the length of the jean really is the deal breaker if it works or doesn’t. As for the skinnies. Its amazing how our eye changes. I was not going to give mine up and now I never reach for them and they look very dated to me, but they did look the best with longer cardigans, which I really like, but feel dumpy in with the newer style jeans. If you plan to still wear your longer cardigan’s, maybe a fun post on how to wear them now without looking frump would be an idea. 🙂

  7. PS I just had to do another PS, as I just noticed the CLICK TO SHOP at the bottom of the graphic. That is so convenient to shop the items on the graphic. Great job and didn’t want anyone to miss it. You really do put in a lot of work Jo-Lynne.

  8. I LOVE this post!!! Thank you so much! I just cleaned out over 45 pieces from my closet and shoes are next on the list. I have added a couple of new jeans to my closet, full length boot cut and cropped flares, and I’m so excited to wear them. This is a priceless guide and it is going on my closet bulletin board today! Thank you again. Have a great weekend!

  9. Jo-Lynne, Thank you so much for doing this post and for putting together the graphic! You have no idea how helpful that is going to be. It sounds like you are going to have a fun weekend. Enjoy, and Happy Early Birthday to Becca!

  10. Another, THANK YOU so much for the helpful post. After spending a day trying on jeans and shoe/boot combinations for an upcoming trip, your post is just what I need to confirm or adjust some of my decisions. Thanks for keeping us current!

  11. I haven’t been able to find a pair of straight-leg ankle jeans that fit me properly. I am petite and short-waisted and everything is so high-waisted. After reading your blog post, I found a mid-rise pair and decided to buy them and cut them off. I wore them yesterday, and they are just perfect. Thanks for your help.

    1. Jen……Do you mind sharing which jean you bought? I have the similar issue and so far have found I do well with Wit and Wisdom jeans, but would like to know the brand you bought that Jo-Lynne recommended. I too have to sometimes cut mine to get the ankle affect.

  12. I am having a fit trying to find the “right” pair of black jeans! Do you find the FRAME Le High to run true to size and that they hold their shape? Also, are the ones linked above the exact match as what you are wearing? I love the somewhat variegated look of the ones you have on in the photo, but on the Bloomingdales site, they look more consistently black.

  13. Well if this blog post isn’t one of your top 10 when you look at your year in review I’ll be shocked! What a great idea!!! I definitely took a screen shot and will refer to it when I’m indecisive getting dressed or out shopping! Thank you and have a great weekend! This is our Canadian thanksgiving so it’s many turkey dinners on the menu and time with friends and family!

  14. Great post! I love the infographic. I’m planning on making a quick stop to look at shoes and denim after I leave the office today and this is so very helpful. Also, thank you for including skinny’s. While I haven’t pulled mine out yet this year, I know I have the perfect pair of boots I can wear with them to keep them looking updated. Plus, I sometimes on Friday used to wear black leggings, a long workout top (that covers my crotch) with a long cardi and knee boots. I’m exicted to try that combo with my lug soles to freshen it up.

  15. WOW!!! You totally knocked it out of the park with this one!!! I saved the graphic and put it in my “Outfits” album on my phone. You put so much time, effort, energy, and work into this and it shows. Thank you!!! Have a wonderful weekend and Happy Birthday to your Becca!!!

  16. Do you think Doc Martens/Combat boots are still in style? I was going order a pair since I’m traveling to a very wet and windy area,having my doubts now lol

    1. Definitely! Very much so. My daughter has a pair she wears a lot during the winter. They pair well with straight leg jeans — especially a relaxed straight with a cuff.

  17. Wow!Just Wow! This is fabulous! Now I really know why you are my favorite blogger. You are the first blog I read every day and always get the best pure fashion advice. Great job.
    I’m so tired of bloggers showing off where they are going, what they are eating, or how fancy their house is.
    I’m just here for help navigating the fashion industry.

  18. The straight crop “category” would be the jeans/shoes collection I would (and do) keep going back-to the most. Happy weekend!

  19. I’m a little late to the party but still wanted to let you know how much I appreciate the work you put into all these denim/shoe pairing posts. This one is the crown jewel! Amazingly helpful! I love the graphic. Thank you so much!

  20. This graphic is so helpful. I love to wear clog type shoes and this is one of the few times I have seen recommendations for them. Also, I have two pairs of jeans with cuffs at the bottom and I struggle to figure out the shoes. One pair is full length and one pair is ankle length – do you have any recommendations?

  21. Jo Lynne,
    This is so helpful. Thank you so very much for doing this. You have been working overtime on these posts. You are the best and I appreciate it. I did order some gifts for my daughter in law, and I want the My Place pot for myself. I am in the market for a solid black pointed toe shoe. Has to be flats. I am in 2 chorale concerts in December and I have to have a flat shoe because of standing for over 2 hours singing. Can you recommend a shoe for me. Again, Thank you for all your great posts this month. Happy Thanksgiving to you and your family. God Bless you all!!!Bev Brown

      1. I absolutely love this! However one style pants and shoe type I don’t know how to pair are winter snow boots! I only know how to pair skinny and maybe straight legs with snow boots. But flares and mom jeans?

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