Top 10: checked shirts

Shanna Schreuder

Copy Producer, Menswear,

1. College preppy

Channel the Ivy League look with the Gant N.Y. Upper East shirt, a pair of khaki chinos and a loafers or boat shoes. Go a step further and drape a v-neck jumper over your shoulders or slip on a navy blazer. Like a lot of the shirts, it also features a chest pocket to keep your work pass or travel card.

Gant N.Y. Upper East Poplin Shirt

2. Formal affair 

Cut with a tailored fit, bold checks and a contrasting semi-cutaway collar, this smart piece stands out for all the right reasons. Wear it with a single-breasted suit and plain tie or jeans and a chunky knit.

John Lewis Tailored Check Shirt, Navy/White

3. Autumnal hues

Be bold with this Timberland shirt. The orange works to add warmth and complements the other shades. Couple it with more neutral-coloured trousers or a pair of mid-wash jeans. Do the same when it comes to the shoes, and pick tan brogues or brown boots.

Timberland Wool Check Shirt, Sun Dried Tomato


4. To the top

Ben Sherman likes its shirts to be buttoned all the way to the top to conjure up an indie rock look that’s such a major part of the brand’s heritage. Create it by teaming this one with slim-fit jeans and a pair of pointed lace-ups with polished uppers.  

Ben Sherman Tattersall Check Shirt

5. Slim cut

Cool and contemporary, this shirt goes with suit trousers and waistcoat, slim jeans and a lightweight blazer, or chinos and fine knit. It’s darted at the back to create that covetable fitted appearance, which also means it fits beautiful under a tailored jacket. So many outfit options for you to pick from.

Kin by John Lewis Stanworth Check Shirt

6. Honorary check

Born in Malaysia, “gingham” comes from the word genggang, meaning “striped”. It lost its original meaning when it travelled to the West and now is considered to be more of a check pattern. Whatever you want to call it, it’s a firm favourite amongst many fashion brands and so should have a place on this list.

Fred Perry Panel Gingham Shirt, Red

7. Heading west

You’ll want to keep your colour dial on monochrome for a tad longer when you see this black and white shirt from Diesel. The press-stud buttons and wingtip detailing add a cowboy flavour that fits in nicely with the shirt’s no-nonsense shades.    

Diesel Spoltava-R Check Shirt


8. Weekend option

Heading to the pub on a Saturday night doesn’t require much effort in the wardrobe department. For example, this Tommy Denim shirt with small checks add colour and smartness to your look without going overboard. All it needs is a pair of jeans and some loafers.

Hilfiger Denim Abi Check Shirt

9. Smart days

Update your office wardrobe or get your outfit ready for an upcoming wedding with Thomas Pink’s slim-fit shirt. The very fine checked pattern helps to add depth to the pure-cotton fabric. Cut to fit a little closer around the chest, waist and hips.

Thomas Pink Alpha Check Shirt

10. Go tartan

The Scottish brand Lyle & Scott is spreading the love for its nation’s traditional pattern with this tartan shirt in green, yellow and red. Offering a slimmer fit than usual, so make sure you get a size up from your regular size. As it has a bit of navy in it, you could team it with navy chinos.  

Lyle & Scott Vintage Slim Fit Check Shirt