How to Wear Cropped Pants: Styled Unique Ways

The question of how to wear cropped pants is something I hear from many women. We’ve gotten very used to the skinny jeans and automatically think that this new trend won’t work on us.

BUT STOP!! I want you to think back to when the skinny jeans first came out. Were you a fan at the beginning? If you were anything like me, you thought no way that could you wear them. And yet, the more we saw other women wearing them, the more we thought to try it.

And then? Then we became fans of skinny jeans and found how they could work for our individual body and how to style them with things in our closet.

The same now holds true with any new trend that surfaces. It looks strange to our brains because we haven’t seen them much and we tend to automatically think they won’t work.

The only way to find out how to wear cropped pants is to try them on. AND NOT JUST one pair!! There are going to be differences galore in the styles and brands, so have an open mind!!

And leave it to me to come up with 5 different ways of how to wear cropped pants with contrasting tops, all kinds of color combinations along with a variety of shoe choices.

I'm showcasing 4 ways to style this pair of cropped pants here, and there's an additional outfit on my blog.

These Cropped Pants

This pair of pants was purchased as part of my Target collaboration with 4 other women.

They are available in other colors and even women’s plus sizes. But most of us agreed that they run a tad large, and you should order a size down. I couldn’t do that so my mom helped me out and took in the waist for me.

They are mostly cotton with 2% spandex, and that’s one reason they get wrinkled. Now laugh if you want, but I’m trying to embrace the wrinkles in my clothes AND on my face.

Why should you try the cropped style? I will say that these shorter styles are great for showing off our fabulous shoes. Just like the three of us showed recently with ankle pants, cropped pants, and cropped flares.

Plus if you continue to wear the same silhouette pants when the styles have changed, it can give off an air of frumpy.

Wear a Short Top with a Hem Detail

Of course one way I didn’t showcase here is wearing your top tucked into the cropped pants. But since many women don’t love that idea, I decided to try two different ideas with tops instead.

The first idea is choosing a top that isn’t tight or too long. If it has some kind of flare or detail at the bottom, then it looks intentional that it shouldn’t be tucked in!!

Shoes: I wore my peep toe heels with this version to add in an unexpected color You can see  5 other ways I’ve worn these thrifted shoes recently.

Color: Here I’ve paired the mint pants with a neutral top and added in color with the shoes and accessories.

Insider tip: The idea to layer necklaces could be used if you are worried about how the pants look and want to draw attention up to the top half of your outfit.

Tie Up You Tee

Another way to style a top would be to tie it up so it’s not as long. This idea creates a different proportion than if you had left the shirt hang down.

In fact, I went a step further and tied one of my Gibby’s scarves around the knot. I still have a discount for 25% off Gibby’s scarves if you go through my link.

Insider tip: I talk about 3 different ways to tie up long tees in a YouTube video.

Shoes: Flats are an easy option, and just like in the first version, I tried a different color than the pants.

Color: I mixed blue and mint together. I wasn’t sure about the combination at first, but I like pink and red, so I reasoned that green and mint aren’t any different. Then I threw in orange with the shoes and accessories.

How to Wear Cropped Pants with Jackets

I showed this and another jacket from every angle in a video on Instagram. Even though I wore a jacket, I did tuck in the top underneath and even added a belt to match.

Shoes: I showed a pair of Walking Cradles (15% off with JODIE15) “Shine” ankle boots. Many times our longer pants hide our boots, so this length is great for showing them off.

Color: This shows a neutral jacket looks great with the same mint pants. In the video you'll see it paired with a bright color jacket too.


Kimonos are the perfect layer when it’s warmer outside. Since they come in all different lengths, I chose one that was longer than the jackets yet shorter than the cardigan below. While the proportions aren’t the ideal ones in this outfit, I think it still works because it’s more open in the front.

Shoes: Sneakers are always a good option since they should be comfy and come in so many fun designs now. This is my Jambu pair called Lilac (even though they are pink) and JTOUCHS21 is still good until the end of May.

Color: This example shows all kind of colors that I took from the kimono. I love how it incorporates both bright colors and lighter colors.

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Jodie Filogomo
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