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.
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 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.
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.