How to Wear Cropped Jeans: 4 Ways to Style Them for Fall

How to wear cropped jeans and what to wear with them. Styled 4 ways by Toronto fashion blogger

As a die hard skinny jean lover I cringed when cropped straight leg and flared jeans started growing in popularity. I promptly swore them off immediately. But here we are a few seasons later and I’ve finally decided to join the club. And it turns out, once I figured out how to wear cropped jeans, I quickly fell in love with them.

Being on the petite side, I had stayed away from wearing cropped jeans for so long because I felt like they would visually shorten my already short legs. But when I got these cropped jeans from Numero, they completely changed my mind. They were the perfect blue wash and being so soft and comfortable I found myself wearing them all the time. And while cropped jeans used to baffle me, once I realized how to wear cropped jeans I became completely and utterly obsessed,

I’ve really come to love the relaxed crop jeans feel. And found they were also a little more interesting and on-trend than your average skinny jean. So here are some of my personal styling tips on how to wear cropped jeans along with 4 cropped jean outfits for fall!

Check out more of my fashion posts:

How to Wear Cropped Jeans – Styled 4 Ways

What shoes to wear with cropped jeans: Option #1 mules are great option as they show off a little ankle and lengthen the legs

1. Show a little ankle

When it comes to styling cropped jeans, knowing what shoes to wear with cropped jeans is very key.

If you’re worried about cropped pants truncating your legs, try wearing them with a shoes that shoes a little with of ankle like a mule or slide style sandal. While showing a little ankle is sexy, it also helps to elongate the legs.

I also find wearing cropped jeans with a mule looks very modern in an effortless chic way. It’s one of my personal favourite ways of wearing them.

In this outfit here, I’ve pair my boot cut cropped jeans with an almond toe mule. The almond toe mule helps to lengthen the leg by showing off more of the leg and extending the foot with the almond shape toe.

To keep things casual, for this look I’ve paired my cropped jeans with a simple cami and balloon sleeve sweater. It’s the perfect weekend casual look for fall that’s checks off both boxes for chic and comfortable.

How to wear cropped jeans: 4 types of shoes to wear them with style by fashion blogger Eileen Lazazzera of YesMissy

2. Embrace the Casual Nature

Cropped boot cut jeans have a natural relaxed sense about them. So embrace the casual nature of cropped jeans and rock them with sneakers and a sweater.

Like the previous tip, I like to wear them with a low cut sneaker to show off the ankle and lengthen the leg.

This is one of my go-to daily outfit combinations for when I’m wearing my cropped denim. I love it because it’s an easy look that can be thrown together in a flash, but something about the cropped denim gives adds that it factor.

How to wear cropped boot cut jeans: this look dresses up cropped jeans with a blazer and pointed to sling backs style by YESMISSY

3. Get Elevated

To dress up them your casual cropped denim, try wearing them with a pair of pointed toe shoes. This is a great way to elevate the look, plus wearing a pointed toe shoe is another leg elongating tip. Then throw on a blazer and you’re all set!

For this look, I’ve decided to do a mix of casual and office. I dressed up cropped boot cut denim with some pointed toe sling backs and a blazer, but dressed the look down by pairing them with a casual striped tee and a newsboy cap. Together it’s the perfect combination of every day with a little edge.

How to wear cropped jeans with ankle boots styled by fashion blogger by YESMISSY

4. Boot Up

When it start getting chilly, wearing boots is a great option for how to wear cropped jeans in the winter and those chillier fall days! Just make sure they’re a pair that are slim around the ankle or a lower cut ankle boot. Either of these option creates a more flattering leg lengthening silhouette.

In this look, I’ve styled my boot cut cropped jeans with slim suede ankle boot, a sweater tee layered with a wool coat and accessorized wool floppy hat. It comes together as a great daily fall look that will keep you cozy and comfortable as the weather gets cooler.

Liked this post? Check out more fashion posts here:

How do you like to wear your cropped jeans? Let me know in the comments below!
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Share your thoughts...

  • Danielle
    September 13, 2020

    I love cropped jeans, they are my absolute favourites!


    • Eileen
      September 13, 2020

      Thanks Danielle! I still love my skinnies, but I’ve fallen in love with cropped jeans too!

  • kathrineeldridge1
    September 13, 2020

    You style these jeans so amazing! My fave is the last one with the suede booties and hat. So chic!

    • Eileen
      September 13, 2020

      Thanks so much Kathrine!

  • Anika May
    September 13, 2020

    I love your style! The cropped jeans with boots is definitely my favourite look, perfect for autumn too 🙂

    Anika |

    • Eileen
      September 13, 2020

      Thanks so much Anika!

  • Monica Hein
    September 13, 2020

    Loving all the outfits

  • crystalsandcurls
    September 14, 2020

    Eileen, all of these looks absolutely slay! I love #3 best I think … I’m a big fan of cropped jeans because I hate the look of jeans being bunched at the end xx

    • Eileen
      September 14, 2020

      Thanks Mia! Oh I remember when that was popular too, it was rather unflattering, well on me at least!

  • Hannah
    September 14, 2020

    I don’t tend to wear jeans, and I’m still trying to find my perfect pair. This is so helpful, as I must admit that I’m a bit clueless when it comes to styling them xx

    Hannah |

    • Eileen
      September 14, 2020

      It can feel like finding the perfect pair can be and endless quest, but totally worth it when you find them!

  • Suzan J
    September 14, 2020

    Being taller, jeans tend to be cropped a lot on me, and I’ve really fallen in love with the look! Love this post <3

    • Eileen
      September 14, 2020

      Thanks so much Suzan!

  • shealennon
    September 14, 2020

    Perfect timing! My favorite pair of jeans I just got are a cropped, relaxed and distressed pair, so I am loving all this outfit inspiration for ways to style them!

    • Eileen
      September 14, 2020

      Thanks so much Shealennon! They sound like the perfect pair!

  • Patricia
    September 14, 2020

    I love the cropped jeans look you put together, suits you so well! Bisou from Berlin

  • Desirèe
    September 14, 2020

    Wow great styles!

  • Shauna
    September 14, 2020

    So many fun ways to wear them!


  • Ella pretty blog
    September 15, 2020

    These all look so cozy and perfect for Fall!

  • Cielo Fronteras
    September 16, 2020

    Such great styling… I love everything! =)

    – Cielo
    Mermaid in Heels

    • Eileen
      September 18, 2020

      Thanks so much Cielo!

  • Nikki (@NikLivingLife)
    September 17, 2020

    I have not tried cropped flare pants. But your styling inspo making me want to give it a try. Love all the looks you created and your tip on pairing with pointed toe shoes. Thank you beautiful.


    • Eileen
      September 18, 2020

      Thanks Nikki! You should give them a try, I didn’t love them at first, but now I’m obsessed!

  • Mica
    September 21, 2020

    They are such great jeans on you and I love all 4 ways you’ve worn them! I really like them with the boots especially for cooler weather 🙂

    Hope you had a great weekend 🙂 Thanks so much for joining the #WeekdayWearLinkup!

    • Eileen
      September 23, 2020

      Thanks so much Mica! Have a great week ahead!

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How to Wear Cropped Jeans: 4 Ways to Style Them for Fall