15 Cute Outfits With Checkered Pants

Hello beautiful! Thanks for being here. We’re going over something important in this blog: checkered pants!

Have you ever worn a pair of checkered pants? Checkered, not plaid. There is a difference, which often gets mixed up or used interchangeably. Here is how you can tell the difference between the two! 

Plaid prints have parallel lines that run both horizontally and vertically. The colors will differ, and the amount of lines that are present will vary, which means the squares will be different sizes. Fun fact, these originally were called Tartans!

Checkered prints can be of varying colors, too, but the squares will all be symmetrical, meaning all the same size.  

So, how do you wear such a busy pattern without looking a bit crazy? Well, that’s where I can help you! Here are 15 cute outfits with checkered pants that you can replicate!

1. Black Checkered Pants with Camel Coat

Here, we see a pair of black pants with white lines. It’s not a super bold, checkered pattern because all of the checker squares are black, which makes them a super easy pair of checkered pants to wear for a variety of occasions.

She’s picked a black shirt, black vinyl shoes with white soles, a black bag, and added a pop of color by draping a camel colored jacket over her shoulders. So even if you’re not into bold patterns, you can easily rock this!

2. High Waisted Checkered Pants with Sweater

I love how effortless this outfit is here. A perfect one for grabbing a coffee or food with a friend! These small, black and white checkered, high-waisted pants are super cute. Her addition of a gray, loose-fitted, cropped sweater and white chunky sneakers is perfect with them too. 

It’s casual and not over the top. If you wanted, you could swap the shirt for a graphic tee or even a plain one!

3. Checkered Pants with Mules

These black and white checkered pants are similar to those above, but this has a white ribbed sweater tucked in. Note that this sweater has vertical stripes, which goes to show that you can mix other patterns with checkered pants!

She’s wearing a pair of black pointed toe mules that matches not only the black checks on the pants but a black hat that you can just barely see in the picture. Wouldn’t this be a great work outfit or dinner date outfit?

4. Blue Checkered Pants with Floral Shirt

Oh, isn’t this such a cute outfit?! I love all the colors. Blue and white checkers with a green button up blouse and floral print on it. The color combination here is awesome, but what I really love is how she added pink heels! 

This is a great spring or summer outfit and is a cute way to wear all of these colors!

5. Pink Checkered Pants Outfit

Another great way to rock colored checkered pants! These pink and white plaid pants are super playful and a great combination of pink shirt with white-trimmed sleeves. What I really love, though, is her addition of the yellow bag. It’s so cute next to the pink and white checkers. 

A cute pair of nude heels to strut her stuff in and she’s ready to go!

6. Vintage Checkered Bell Bottom Pants

THIS IS SO CUTE! Such a retro vintage look with these bell bottoms (which we’re seeing a lot of recently). She’s even got the color pallet down, with brown, orange, yellow, blue, and black.  

A knotted graphic tee was the perfect addition for these high waist, bell bottom, checkered pants. It shows a little bit of skin and gives some texture to the look, although the pants are totally enough.  A pair of tan suede boots beneath is perfect! A pair of white sneakers would work too!

7. Checkered Leggings and Graphic Tee

This outfit speaks to my soul, because I truly love my Dr. Marten boots and a good graphic tee. Even better that they’re being worn with these black and white checkered pants. This is a great example of how the pants don’t need anything fancy worn with them. A simple white graphic tee is plenty!

8. Oversized Checkered Pants

Here is a cute fall outfit that is probably incredibly comfortable! These pants are fun because they’re loose fitted and she’s rolled the bottoms up to show off some ankle and her white converse.  Take these two right here and add any color top you want! 

This mustard yellow sweater is perfect, but you have all the freedom in the world with what top you’d want to wear with it. Yep, they’re that universal. Great, right?

9. High Waist Checkered Pants with Mesh Top

If you’re not wanting to wear a complete crop top, wearing one (or a bandeau) underneath a mesh top is a great alternative. She even went as far as putting a denim jacket over her mesh shirt that’s tucked into her high waist, checkered pants. This is also a great way you can up the sexy factor with these pants! There are some cute bralettes that look great beneath mesh tops which would make a pair of checkered pants sexy club or concert worthy!

10. Beige Checkered Paper Bag Pants

Eek! This is such a cute pair of checkered pants, I can’t get enough! I love that they’re a beige and white checker combination, it’s a very spring and summer vibe! A white v-neck bodysuit or tank tucked into the top of the paper bag waistband of the pants was the perfect top selection.

I imagine she’s wearing nude heels with this outfit! If it were me, I’d probably stick with nude pumps or strappy sandals (black would work too), white mules or slides, or maybe a pair of white sneakers!

11. Classic Street Checkered Pants

Checkered pants during winter clearly don’t disappoint! She’s rolled up the bottoms to give room for some boots similar to Dr. Martens, a Nike sweatshirt, and a mustard yellow puffy jacket to match the Nike check. This look is very street!

12. Green Checkered Pants Outfit

Here’s another great street look featuring green checkered pants! I’m all about the colored ones! I say this is street, because unless you work in a skate shop or hip retail store, this would only be a casual wear outfit. 

I love that she’s wearing these vinyl pointed toe Chelsea boots that match her leather jacket and beanie. A black, graphic tee looks cute tucked into her checkered pants. 

Check out my Chelsea boot style guide to see more great boots like these!

13. Loose Checkered Trousers & Neon Tee

I’ll admit, this one isn’t quite my taste but the reason I wanted to show it to you is because there are a few things in this outfit that are trending right now. 

But first, some high waist, loosely fitted, black and white checkered pants. She’s tucked a neon graphic t-shirt into it, which is a big trend right now.  Then there’s the white chunky sneakers which are also trending at the momentㅡcheck out my white sneaker blog! 

There’s a lot that could be done to amp up this outfit, such as adding a hat, a fanny pack, or even a vibrant shoulder bag. It’s definitely very early 90’s!

14. Chunky Stripe Checkered Pants

Here’s another almost retro inspired, checkered pant outfit, but I think it’d be a great one for both out on the town and work! I like the boldness of the white in these and that her earrings are square so they tie in together! A black top, bag, white heels, and a camel coat all complete this look! 

Camel, black, and white all look so good together, don’t you think?

15. Classy Large Checkered Pants

Say hello to these big chunky checkers! I’m into the pink, black, and white happening here in this outfit. This pink blazer with the bell sleeves is super cute and almost preppy with the black tieㅡwhich by the way, matches the black bow on these crazy cute heels!

But let’s get back to these large checkered pants. They’re bold, but not as visually busy as smaller checked pants! A cute work or special event outfit! 

Okay so, now that you’ve seen several different types of outfits with different types of checkered pants which is your favorite? I love to wear plaid and checkered patterns, so I’m a fan overall, but I think number 6 is super adorable!