How to Wear Cropped Jeans (11 Outfit Ideas!)

Cropped jeans? You’ve seen them everywhere but how do you actually wear them without looking ridiculous? Well you’re in the right spot because today I’m going to share some tips and trick for how to wear cropped jeans.

The first thing you need to realize is this. If it’s been a minute since you’ve worn a pair of cropped jeans whether they’re cropped flare jeans, cropped straight leg jeans, cropped wide leg jeans or any other type of cropped pants, you’re likely going to feel a bit out of your comfort zone. They’re new. You’re not used to them…yet.

Part of trying new trends is getting the confidence to wear them out in public. Start by wearing them around your house a bit to get used to them.

Take photos of yourself in the mirror to see what you think in photos. Sometimes seeing a photo of yourself in them makes you love them way more than just seeing a reflection in the mirror.

(Sound crazy, I know, but try it!)

Nobody has the same body type and everyone has different style so today I’m going to share a variety of outfit ideas to inspire your next cropped jean outfit! From casual to dressy, I hope these outfits get you excited to try out your very own stylish outfits featuring a pair of cropped jeans.

11 Cropped Jean Outfit Ideas

Paisley + Sparrow is a participant in the Amazon Services LLC Associates Program. This post may include affiliate links which means I may earn a small commission if you shop using the links below at no additional cost to you. 

Here’s some of my favorite cropped jeans!

Let’s get started with some outfit ideas.

1. With a Ruffle Sleeve Top and Boots

cropped jeans and floral top

Shop this look: Jeans | Long Sleeve | Boots (sold out, similar here)

Want a trendy look? This is a great look for you! This fun floral print top has ruffle detailing on the shoulders and a button down back to dress up what could be a casual look. Tuck the shirt in tight for a sleek look and throw on a pair of booties for some height. You’re ready to rock your day!

I prefer to have booties that are high enough to be fully covered by my jeans rather than having a bit of skin showing. This will depend a bit on the where your jeans fall!

2. With a T-Shirt and Gladiator Heels

cropped jeans and tshirt

Shop this look: Jeans | T-shirt (sold out – similar here) | Heels (sold out – similar here and here)

Take the jeans from above and make it spring appropriate! An easy way to transition from winter to spring is to swap a long sleeve for a short sleeve and boots for sandals.

I like these gladiator heels since I have short legs and they elongate my legs a bit but the simple tee keeps the look nice and casual.

3. Basic White Tee & Sneakers

cropped jeans and nike sneakers

Shop the look: Jeans | T-shirt | Sneakers (sold out, similar here)

Casual yet chic? Yes, please! The best way to ease into a new trend is to keep the rest of your outfit neutral (yet chic!). A neutral t-shirt with cute shoes (like these Nikes) will get your comfortable with cropped jeans before you go all out with a more wild outfit!

This simple yet pulled together look is perfect for grabbing coffee with a friend or running errands! Easily swap the fun sneakers for a pair of white sneakers or flat sandals!

4. White Tee, Fleece Zip Up & Sneakers

cropped jeans and fleece

Shop the look: Jeans | T-shirt | Fleece (sold out, similar here) | Sneakers (sold out, similar here)

On a cooler day throw on a fleece zip up over your white top for an extra layer of warmth! Tuck or knot your t-shirt to show your waistline and create a more flattering look, especially for jeans with a higher rise.

Throw on your favorite sneakers (opt for a low cut sneaker over a high top) and out you go!

5. Blazer & Heels

cropped jeans and blazer

Shop the look: Jeans | T-shirt | Blazer (sold out similar here and here) | Heels (sold out, similar here)

I’m a big fan of blazer – maybe you are too! If you’re looking for an outfit for date night or the office, try this combination! Blazers are trending right now and look amazing when paired with cropped length pants and a pair of high heels. Wear black under the blazer for a slim look and to keep things professional if heading to the office.

Swap the colored heels for black or nude high heels if you need something more muted like casual Fridays at the office!

6. Black Boots & Bat Wing Cardigan

cropped jeans and batwing cardigan

Shop the look: Jeans | T-shirt | Cardigan (sold out – similar here) | Boots

Another easy look is cropped jeans with a cardigan! Petite women often feel like they can’t pull off longer cardigans like this one. Some tips are to wear heels or heeled boots to create long lines and tuck in your top to define your waist.

Be sure to skip the super wide leg pants if you’re opting for a longer length cardigan so you’re not swimming in fabric.

7. Denim Jacket & Chelsea Boots

cropped jeans denim jacket

Shop the look: Jeans | T-shirt | Denim Jacket | Chelsea Boots

Chelsea boots are hot right now and obviously so are cropped jeans. Combining them is a great option! If you’re layering a jacket over the top, especially if it’s an oversized one like this one, always try to define your waist in some way.

I tucked in my t-shirt to give my waist some definition or you could try a cropped top (if you’re comfortable with that). There’s a variety of different ways to knot or tuck your shirt but doing so shows off your waist to create a more flattering look!

Find more Chelsea Boot outfits here!

8. Sweatshirt & Chelsea Boots

cropped jeans and sweatshirt

Shop the look: Jeans | Sweatshirt | Boots

Need a throw on and go kind look? This one is just for you! Cropped jeans and a sweatshirt make a perfect pair – you’re able to feel cozy and casual but still look chic with a trendy style of jean.

Throw on a pair of Chelsea Boots to complete the look!

*Find more Chelsea Boots outfit ideas here!

9. Sweatshirt & Nikes

cropped jeans and sweatshirt

Shop the look: Jeans | Sweatshirt | Sneakers (sold out, similar here)

Is the weather too warm for Chelsea Boots but you still want to wear a sweatshirt and cropped pants? Don’t worry! Swap the ankle boots for Nike sneakers and you’re good to go!

10. All Dark

cropped jeans and bodysuit

Shop this look: Jeans | Bodysuit | Boots (sold out, similar here and here and here)

When in doubt, go dark! When trying a new trend sticking with subtle hues is your best friend! These grey wide leg crop pants look super chic with my black bodysuit. If you’ve never tried a bodysuit yet – you need to! They create the perfect fit for a tucked in top kinda look.

Throw on a pair of white booties if you’re feeling funky or black if you want a monochromatic look (with a black bag to complete the look)!

11. Cozy Cardigan Sweater

cropped jeans, white booties and cropped white cardigan

Shop this look: Jeans | Cardigan | Boots (sold out, similar here and here and here)

An oversized sweater and cropped jeans can work well together! Here’s a few tips. Opt for a shorter top over a longer top if you’re jeans are on the wider side (if they’re skinny jeans you can go with a longer top)!

Want more white bootie outfit ideas? Head here!

Need tips on tucking your shirt? Read this!

There you go! I hope these 11 outfit ideas inspired your next cropped jean outfit and allow you to get more use out of what’s in your closet.

If you need some inspiration on other cropped jeans, check these out!

If you want more posts like these, check out one of these!

About Jen

Jen is a mom of 3 who loves frozen cookie dough, plants and a generous pour of creamer in her coffee. Her biggest joy is helping others find joy in their life, style and home through tips, tutorials and encouragement. She also runs 2 additional blogs. Feel free to send Jen a message or join the fun on Instagram!

Leave a Comment

7 Cropped Jeans Outfits to Try Today
7 Cropped Jeans Outfits to Try Today