What shoes to wear with a check shirt

Although check shirts are about as basic as most wardrobes get, it can still be tricky to match them up with other garments – especially shoes – as there’s usually no single colour to pick out. However, choosing clothes to pair up with check shirts doesn't have to be difficult when you aim for a mood rather than a specific look. Think laid back and informal, and use the principal colour merely to guide you rather than to lay down the law. Here’s our brief guide.

How do men wear check shirts?

The check shirt is a versatile garment. It can be worn over a t-shirt, with jeans or canvas trousers, open-necked or buttoned up, with boots, shoes or trainers. The weight of the fabric determines how informal it is and what it’s best worn with.

At its heart, the check shirt is a modern interpretation of the tartans, Ginghams and buffalo checks that have been used in shirtmaking ever since weaving was invented. It’s rarely worn formally as the check can clash with a jacket. The exceptions are when the squares are tiny, such as pin check, or widely spaced, like a graph check.

For a light check like Gingham, you’ll look smart with a pair of narrow jeans and Chelsea boots – a professional urban look that’s never going out of style. For bolder, heavier checks, a decent pair of 6-inch boots are always going to work. 

What is a checked shirt?

Checked shirts are made from fabric with two or more colours of thread, creating a pattern that can be simple like a chequerboard, or more complex, like tartans or houndstooth checks. Some check shirts have the pattern printed onto plain fabric, however.

Checked patterns are great to pair with as all the hard work has been done by the designer of the fabric. All you need to do is pick out the dominant colour and pair up against it, usually using the secondary colour as a guide.

It’s a good idea to avoid the main colours when it comes to choosing your trousers and jacket, so pairing a green/white Gingham shirt with blue jeans will work a treat. If the secondary colour is black, however, wearing black jeans and black boots is always a good option as you’re guaranteed to avoid clashing or having a single overwhelming colour.

What is a plaid shirt?

Plaid is the family of weaves where two or more colours are blended together in a repeated geometric pattern. Tartans, houndstooth, graph and shepherd’s check are all examples of plaid, although shirts tend to be Gingham or buffalo check unless they’re particularly dressy.

Red is a popular choice for a plaid shirt as it goes particularly well with blue jeans, which is by far the most common type of legwear worn today. If you prefer lighter pants such as beige chinos, a more muted plaid is preferable – a blue, green or lighter check, for example.

Are all flannel shirts plaid?

If we’re being accurate, flannel is a fabric, not a pattern. The appearance can therefore be plain, plaid or anything else. Plaid is the overlaying of two or more colours in a weave, like check or tartan. Colloquially, however, flannel shirts tend to have a plaid pattern.

Flannel shirts normally refer to those with more than two colours, such as the blue, black, white and red interaction in this Eastham River shirt. A larger arrangement can be used in the flannel shirt, too. A wider pattern has larger areas of single colour, with the plaid bringing mood or punctuation. All flannel shirts have casual undertones, so pair them with whatever jeans are fashionable and step into a pair of smart boots and you’re ready to hit the streets.

Check shirts – easy to pair with

Pairing with a check shirt is easy. Just remember to note whether it’s casual or formal – most are pretty laid back, so jeans, boots or trainers will all work perfectly. If it’s a lighter check shirt, it might be a little smarter, so wear it buttoned up with canvas pants and shoes, but you’d have to go really over the top to make it look too formal. 

At Timberland, our collection of checked shirts has something to suit every occasion, whether you’re heading for a meal with family or drinks with friends. Find the ideal pair of shoes to match in our extensive range of men’s footwear.