Gingham shorts are having a major moment, proving they’re more versatile than their casual appearance suggests. Sure they might remind you of old-school boxers, but these chequered classics have had a serious glow-up, reinvented to look effortlessly chic. If you’re into sporty vibes, vintage glam, or streetwear, these shorts can be styled to make you stand out wherever you go. Ready to take your gingham game to the next level?

Here are five killer ways to style gingham shorts:

Street style edge: Oversized and unexpected 

To give your gingham shorts a streetwear twist, pair them with an oversized graphic tee or sweatshirt. This look is all about playing with proportions—the larger top balances the fitted nature of the shorts, creating a relaxed yet edgy vibe. Finish off with chunky sneakers or combat boots, and maybe throw on a bucket hat for extra style points. Don’t forget a cool crossbody bag to keep the look functional and fashionable.

The jersey shirt combo: Sporty meets stylish 

Turn your gingham shorts into a sporty statement by pairing them with a retro sports jersey. It could be from your favourite team or a classic number; the key is to contrast the structured lines of the jersey with the softer, playful pattern of the gingham. Finish off the look with some high-top sneakers and ankle socks. Add a playful touch in accessories for an effortlessly cool touch.

Two-piece set: Match made in heaven 

If you love a coordinated look, a matching gingham two-piece set is the way to go. Whether it’s a crop top, bandeau, or blazer that pairs with your shorts, this monochrome moment is effortlessly chic. Add a pop of colour with vibrant accessories to keep the look fresh—think a bold colour bag or gold accessories. For a more laid-back vibe, you can opt for neutral sandals and let the gingham take centre stage.

Vintage vibes: Old-school glam 

Tap into that timeless retro appeal by styling your gingham shorts with a vintage-inspired blouse or cardigan. Picture a Peter Pan collar, puffed sleeves, or a knotted blouse. Tuck in the blouse for a polished look, and add a pair of classic ballet flats or mules. Finish with cat-eye sunglasses and a red lip to channel your inner retro queen. This look screams 1950s summer charm with a modern twist.

Preppy perfection: The Oxford touch 

For a preppy, polished look, pair your gingham shorts with an Oxford shirt. Go for a plain or pastel-coloured shirt, and tuck it in neatly. You can pair it with a matching sweater for a relaxed vibe or keep them buttoned for a more structured appearance. Add a pair of loafers or brogues. A thin leather belt and a structured handbag will complete this Ivy League-inspired ensemble.

Gingham shorts or boxers are more than a trend—they’re your new style staple. So, mix it up, have fun, and let those checks take your look from ordinary to stand out!