How to Wear a Check Shirt and Look Great Every Time

Time to pull yours out the wardrobe.

I love check shirts. The pattern is a simple way to add an element to your outfit that catches the eye. They stand out more than plain shirts and striped shirts, and they come in plenty of styles, from toned-down formal shirts to colorful and fun casual ones.

There are also a wide variety of types of checkered shirts to choose from. Flannel or plaid shirts are perfect for casual occasions. It’s easy to wear them on weekend walks or evenings at the bar. Meanwhile, Gingham patterns are perfect for wearing with slacks or under a blazer to differentiate a more formal outfit.

This variety means that what you wear with a check shirt will depend on many factors, including the type of shirt and where you want to wear it. To simplify this, here are some general guidelines to consider:

  • Large checks tend to be casual, smaller checks are more formal.
  • Colorful patterns tend to be casual, muted ones are more formal.
  • Patchwork and asymetrical patterns are an on-trend way to wear the style.
  • If wearing with a tie, keep the tie relatively plain.
  • If you wear with other patterns or checks, make sure they contrast: whether in color or size.

As usual with fashion guidelines, these can all be broken in the right circumstance. But I think they’re a good general place to start before we move on to the outfits.

How to Wear a Check Shirt: 10 Stylish Outfits

1. Over a T-shirt

Flannel shirt over t-shirt chinos
The Brdwlk

Wearing a check shirt over a t-shirt is a classic look. It works best with casual check shirts and plain t-shirts in colors like gray, blue, or white. It’s a casual look so finish it off with chinos or jeans and a pair of sneakers.

2. Over a Sweater or Turtleneck

Patchwork check shirt

Why limit yourself to wearing your check shirt over a t-shirt? Wearing it over a sweater or in this case a turtleneck, is an interesting way to layer up in the colder months. When picking a shirt to wear like this, choose one made of a heavy material like flannel. It should also be generously sized as sweaters are much thicker than t-shirts and you don’t want it to look stretched. Another thing I like about this outfit is how the color of the pocket patches on the shirt match the color of the hat and the rolled up trousers. It’s very pleasing on the eye.

3. With Smart Pants

Check Shirt Black Pants

This is probably my favourite check shirt outfit on this list. The colorful shirt goes really well with the smart black pants. The turtleneck underneath and the black in the stripes gives the outfit a simple background to work from. And the texture of the corduroy pants brings the outfit up a level.

4. Under a Blazer

Gingham check blazer

Wearing a gingham shirt under a blazer is a classic combination. Gingham checks are formal enough to go with the blazer and the blue colors goes well with the khaki blazer. The open collar and sunglasses mean the outfit isn’t too stuffy though. I could see this outfit going down well in offices with relatevly relaxed dress codes. Although you could switch out the blazer and pants for a regular suit if your workplace has a stricter dress code

5. With Contrasting Patterns

Check Shirt Red Suit

Wearing two patterns in a single outfit can be tough to pull off. But I think this one gets away with it because of the huge contrast between the two check peices. First is the different in the size of the checks. The tight Gingham on the shirt contrasts with the large tartan on the blazer. Then there’s the huge different in the colors of both pieces that removes the chance of the two patterns matching too closely.

6. With Skinny Jeans

Shirt Ripped Jeans

The tight plaid shirt and skinny ripped jeans look is a throwback to the early 2010s. But both these items still do the rounds so I think you can get away with it. And if you’ve been working out, undo the top few buttons and roll up your sleeves to show off those gainzz.

7. With Shorts and a Bucket Hat

Check shirt shorts

This is another example of how to combine patterns in a single outfit. This one works because while the shirt is colorful, the shorts have a far more muted gray color. The pattern is also animal print, not stripes, which ensures it doesn’t match the shirt too closely. When wearing a shirt with shorts, be sure to pick a light material like in this outfit.

8. With a Cardigan

Check Shirt Cardigan Pants

This outfit is another example of how to wear different patterns in the same outfit. It works because all the checks are in different sizes and colors. There’s also a brown border on the cardigan that keeps the green from the shirt and the cardigan from clashing. You don’t need to go quite this out there when matching a check shirt with a cardigan. A plain cardigan with jeans or slacks will work just as well, or maybe even better.

9. Under a Casual Jacket

Check Shirt Jacket Jeans
Deposit Photos

You don’t need me to tell you that you can wear a check shirt under a jacket. But what I like about this outfit is how the two shades of green complement each other. Picking one of the colors from the checks and then using it somewhere else in your outfit is a theme that I like and have seen in a few of these images.

10. For a Relaxed Office Look

Here’s another example of a check shirt with a blazer. The muted checks, gray blazer, shoes, and beige chinos mean this outfit will pass in most business casual situations. If you’re looking to wear your check shirt to the office, then give this look a try.

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Duncan Elder

Duncan is the founder and editor-in-chief of The Boardwalk. He's a menswear writer who has spent the last 15 years developing his own sense of style, which lies at the cross-section of mid-noughties indie and Uniqlo-inspired minimalism.

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