Men’s Checkered Pants Outfits – How to Wear and When

Want to make a statement with your fashion? Be bold, dramatic, and even a little classically old-fashioned with tailored checkered pants! When you pair checkered pants with the right pieces, you can harness their dramatic potential while also looking fashionable and modern. View these men’s checkered pants outfits for inspiration!

If you’re looking for custom-tailored checkered pants, shop Berle today! Complimentary hemming and free shipping are always included with your purchase.

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Checkered Pants Are Dramatic – Lean Into It!

If you’re planning on wearing checkered trousers to any occasion, don’t play coy and act as though you don’t mean to make an entrance. Checkered trousers are bold by definition, so lean into that!

This doesn't mean you should go totally crazy with your wardrobe, of course. But you should pair your checkered trousers with more neutral and restrained articles, including your shirt and jacket. This allows your checkered trousers to take most of the attention and highlight your choice.

For example, you can pair soft checkered trousers (i.e. pants with fine-lined checkered patterns) with a subtle blazer or long-sleeve shirt in neutral colors like navy, black, and gray. The key is to not go overboard and pair checkered trousers with other crazy and dramatic wardrobe choices.

Checkered Pattern Styles

There are a few different types of checkered patterns you can find on modern trousers:


Windowpane patterns feature exaggerated perpendicular pinstripes that form plaid squares. These checkered patterns are among the easiest to pull off since they have a strong overall look without being overwhelming. You can easily mix these types of checkered pants with other small-scale patterns on your clothes, including florals, stripes, and even dots.

Houndstooth & Puppytooth

Houndstooth patterns are classic checkered designs that feature alternating bands of four light and dark lines. Puppytooth is similar, but with thinner, softer lines for less of a bold finish.

Prince of Wales

You’ll also be able to find checkered trousers in the Prince of Wales style. These feature irregular checker marks in varying shades, creating a chaotic but visually interesting experience that’s easier to coordinate with sweaters and blazers than the other styles.

Checkered Trousers for Specific Occasions


Explore these checkered trouser outfits for specific occasions:

Formal Looks

There's no denying that pairing tailored checkered pants with formal clothing can be tricky. But you can get the job done by picking your trousers in dark colors like charcoal or gray. Just make sure that the checkered pattern is similarly dark-colored.

Then pair your trousers with soft flannel shirts and strong shoes, such as Oxfords. Make sure that, if you wear a blazer and tie, they also have neutral colors to create the above-mentioned contrast you’re looking for.

Smart-Casual Looks

It’s easier to pair checkered pants with smart casual clothes. Just swap your chinos or similar trousers for checkered pants and you should be set.

Checkered trousers will go well with the other common aspects of this ensemble, like knitted polo shirts or pale blue collared shirts.

Casual Looks

If you want to wear checkered pants to a casual occasion, you can be as bold and vibrant as you like. Just be sure to pair your checkered pants with a white T-shirt or a minimalist trainer to offset the energy of the trousers suitably.

All in all, it’ll likely take a little experimentation before you get your perfect checkered trouser look right.

Shop Tailored Trousers from Berle

We hope you enjoyed these men’s checkered pant outfits. Now that you know how and when to wear checkered pants, complete your look with tailored trousers from Berle. Shop any of our exclusive trouser collections, and enjoy complimentary hemming and free shipping on every order. With more than 70 years in the manufacturing industry, our team has perfected the art of delivering the best pair of trousers available today. Your upgraded wardrobe awaits!

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