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7 Ways To Style Checkered Shirt Outfits For Men in 2024

7 Ways To Style Checkered Shirt Outfits For Men in 2024

The checkered shirt is one of the top wardrobe staples that never goes out of trend and is known as a timeless and evergreen pairing top for men. Checkered shirt outfits are widely popular in the men’s fashion world because they give a clean and timeless look, without worrying too much about matching bottoms.

But, even if they can fit with most of the bottom outfits, there are a variety of styles that can elevate your checkered shirt dressing style to create a decent & confident look while incorporating simplicity and flexibility.

To introduce these styles, we’ve covered and explained the seven ways of styling options to give you an idea about how to style a checkered shirt down below.

So, stay tuned and explore!

A] What Is A Checkered Shirt?

A checkered shirt is a type of button-down shirt that is known for its different intersecting, horizontal and vertical line patterns. These pattern lines give a timeless and versatile appeal, making it a popular choice for men’s fashion.

The history of checkered shirts in men’s fashion traces back to the early 19th century when this shirt gained popularity as casual wear among labourers and outdoor workers. Over time checkered shirts moved into mainstream fashion, favoured by cowboys, lumberjacks and other working-class men for their need for durability and practicality.

Today, checkered shirts come in a variety of patterns and styles that offer a range of options to suit different tastes and occasions. The most well-known variations of this checkered shirt are gingham, tartan, buffalo plaid, and more.

B] 7 Ways To Style Men’s Checkered Shirt

1. Classic Casual Look

Creating a classic casual look with a checked shirt style is a way to give a casual yet stylish look to yourself. Choose darker-wash denim jeans to create a fresh pop of contrast. Further, pair with a checkered shirt and jeans with neutral-coloured sneakers.

Add a leather-stripped watch and roll up your sleeves up to just below your elbow will give a classy yet casual look to your personality. You may layer up your check shirts with tees if you wish to.

2. Smart-Casual Ensemble

There is a variety of styles which can be created using checkered shirt outfits and one of those styles is ‘smart-casual’ together, where you just need khaki or beige colour tailored chinos and suede loafers. Grab a navy or white coloured check shirt and roll the sleeve slightly up for a relaxed and sophisticated touch to your personality.

3. Layered Styling

For creating a stylish layered look, choose a navy or white coloured gingham checkered shirt pattern and pair it with a lightweight complementary-coloured sweater and tailored trousers. To create another polished yet layered look, opt for slim-fit chinos or dark wash jeans, a denim jacket with check shirt layering. Roll the sleeves as per your liking and style.

T-shirts are one of the best layering options for a check shirt dress, to create a layered look, grab a white or black t-shirt and wear a check shirt over the tees. Keep the shirt unbuttoned for a relaxed and effortless vibe and feel. Now, wear a pair of white or black sneakers to tie the whole outfit together.

4. Office-Ready Business Casual

To give you a balance between professionalism and style, creating an office-ready casual look with a check shirt would be a nice idea to consider. To create this, you need a blue and white or black and grey subtle pattern checkered shirt with tailored dress pants in a neutral colour like navy, charcoal grey or khaki.

Add a sleek leather brown or black leather belt and classic oxford or loafer shoes matching with belt colour. You can add a blazer on top to give yourself an extra layer of sophistication as well professional look at the same time.

5. Classic Monochrome

To give a classic monochromatic look to yourself, start with a black and white check shirt and pair it with black slim-fit trousers or tailored black jeans for a polished and streamlined look. Layer with a black blazer to give a sophisticated and formal look while maintaining the monochrome theme.

Add a black leather belt and a simple watch or bracelet in black or silver tones with the classic black leather bag or briefcase to give yourself a polished and professional touch and feel.

6. Weekend Warrior

The weekend warrior looks and style is for those who love adventures or casual outings at the weekend. To create this look, you need a check shirt and olive or khaki-coloured cargo bottoms with hiking boots. If you wish to create a relaxed and casual look, then choose a pair of beige and navy-coloured cargo shorts.

7. Urban Edge

For an urban edge look, start with a tailored fit black and white or grey and charcoal checkered shirt and pair it with distressed jeans for a laid-back yet edgy vibe. Now, choose a classic moto or biker-style jacket in black or dark brown colour to give yourself an extra dose of attitude.

Add a beanie or necklace, because a beanie creates a casual and relaxed vibe to the outfit while a necklace gives you a streetwear-inspired style. Consider experimenting with different accessories to personalize your look and feel.

8. Preppy Charm

Pairing a checkered shirt with well-fitted khaki shorts that hit above the knee for a modern and sophisticated look. Polo t-shirts are also a great option to consider when it comes to the styling of checkered shirts. Add a leather belt, aviator sunglasses and a sleek watch to further enhance your preppy charms.


Fashion evolution has created opportunities for checkered shirts to be a timeless favourite for men. We discussed the various kinds of styles that can be created using a checkered shirt, ensure you try and experiment with a variety of attires to create a personalised look and feel for yourself.

In the end, fashion is all about innovation and experimentation, so go and create a fabulous look for yourself that suits your personality.

We, at Thomas Scott, have a variety of check shirts to give you a cool, stylish and personalized look with a wide range of colours, sizes and designs.

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