How To Wear A Checked Shirt

How to wear a checked shirt
PHOTO CREDIT: Cool Artisan

A checked shirt is a wardrobe staple, with the power to be both smart and casual it really is a versatile piece to own.

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Checked shirts are a wardrobe staple that peak in popularity every few years and never quite go out of fashion. They’ve been worn by everyone, from rockstars to business men, and despite their popularity they always give a unique and eye-catching look to an outfit. You can go for the hipster lumberjack look, the smarter small checked style, the relaxed wide checked look, and more.

With so many styles and colours to choose from it can be tricky to know how to match them. You might also think that it’s only possible to go for a casual look with the checked shirt, but if styled correctly you can easily pull off a smart-casual to smart outfit. So read on and we’ll show you all the ways you can pull off this versatile print to suit a range of styles.




The first thing you need to think about is the thickness of the shirt. A clear indicator for what thickness you should be going for is the time of year and temperatures outside. Autumn and winter are obviously a good time for the thicker checked shirts, and you can wear them buttoned up with a T-shirt underneath for added warmth.

When the warmer months come around, grab yourself a thin cotton shirts, as it’s a breathable material and won’t leave you sweating buckets when the sun decides to shine. You can easily wear that button up on its own or throw it over a short sleeved T-shirt.



Check Style

The next thing you need to think about is the style of the checks. These come in all sorts of designs and can be the deciding factor on whether the shirt looks ready for a dinner date or a day on the ramps. If you go for a shirt with small checks set out in a uniform fashion then try pairing it with a pair of neutral coloured chinos for a more formal look. The small set design is going to give a less bold, and cleaner look that is perfect for smarter occasions.

Wider checks give a more casual look that’s easy to match with a pair of skinny or straight leg jeans. If you stick to two colours then the print won’t look busy, and you’ll be able to keep it as a versatile item that you can mix and match.



Colour is an important one, less for season and more for occasion suitability. A lot of the lumberjack styles come in bright colour-ways and these are far more informal because of their eye-catching tone.

A mix of colours, like red and grey gives the shirt a multi-tonal look that also works well for more causal styles, and can be paired with grey or dark blue jeans. Darker coloured shirts can be worn with dark jeans or chinos and done up to look semi-formal, especially when paired with some brogue boots and covered up with a smart coat, like a peacoat.


Sleeve Length

Sleeve length is an easy one to get right. Summer is obviously a time when short sleeves are a good choice, and matching a short sleeved checked shirt with a pair of tailored shorts and plimsolls is a timeless outfit for warmer weather. If you’ve got a long sleeved shirt that you want to wear in the spring and summer, then there are various ways to turn up the sleeves, for different looks.

If you’re wearing a checked shirt out in the colder months then obviously you won’t be rolling up your sleeves to try and catch some rays. This means that your sleeves have to be the right length. Anything that’s shorter than your wrist is going to look like you got the wrong size, so if you’re taller than average make sure you’re shopping for your body type.


Depending on the weather you might choose to layer up your check shirt with a jacket or coat for some added warmth. Because of the busy print it’s best to go for a simple design without many embellishments, so it’s not competing (and probably losing) against your shirt.

For the summer months you can go for something simple like a light weight denim jacket. If your shirt is a bright colour, like a red, try a lighter denim to compliment the tone, and if you’ve gone for a darker shirt you can match it with a dark grey denim. You could also try a nylon bomber jacket for more of an alternative, street style look, but make sure it’s fitted, as anything too loose isn’t going to work well with the slim lined shirt.


In the winter you can try out heavier designs. Try wearing a thick leather biker jacket over your shirt for a timeless and stylish outfit, and for an added grungy finish, pair it with black skinnies and Dr Marten boots. If you’re going for a more formal look then a navy or black Harrington coat will match nicely, or you can go even further up the formal scale with a slim fit blazer.



Now if you’re deciding to wear a checked shirt in a formal setting, you might have a few questions on what kind of tie to wear with a checked shirt. For example, can you wear a striped tie with a checked shirt? Well, as checked is a busy print, you’d want to keep the tie as subtle as possible whilst still gaining that sophisticated edge that a good tie can add. Stripes, graphic designs and abstract prints will only clash against the checked print and create an eye-watering look.

A good choice is to go for a neutral colour like black or navy, and keep the tie thin so as not to detract or compete with the print. A good tie style is the skinny tie, which gives a smart but alternative edge and is great for a shirt that’s a little out of the ordinary, like the checked shirt.

How to Wear a Checked Shirt

  • Wide checked designs give a more casual look, while small, uniformed checks give a neater style.
  • Choose a thick cotton shirt for winter days and layer it over a plain print T-shirt to avoid an overload of patterns.
  • Try out different sleeve rolls to easily change up your look
  • When picking outwear, go for a simple, un-patterned design so it’s not competing with your shirt.
  • If you’re wearing a tie pick a plain one in a skinny design to add an alternative edge to your outfit.

On That Note

Although the checked shirt is seen as a more casual item, there are a number of ways to create looks to suit your style. You can even pair it with a tie for an alternative look on a smart outfit. Experiment with check design, the thickness of the material and the overall length of your shirt to create unique, stylish outfits to suit any occasion.


A checked shirt is a wardrobe staple, with the power to be both smart and casual it really is a versatile piece to own....
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