24 Oversized Shirts We’re Loving Right Now

With the new AW22 trends hitting our stores, to avoid fashion overwhelm (it’s a thing), the simple shirt is the piece to invest in. It’s a classic, but also so right now – especially if you go big.

Obviously the slimline, tailored shirt looks seriously chic, but this season the phrase go big or go home has never been more relevant in the style world. Blazers are supersized, trousers are baggy and must-have shirts are fabulously oversized for little effort yet maximum impact. 

If you’re still lucky enough to be holidaying on the Mediterranean, the loose-fit Oxford is the sexiest of bikini cover-ups. Fact. However, with the days getting cooler and September on the doorstep, the androgynous look is where it’s at. Take an XL cotton button-down, pair with tailored trousers, throw on that blazer and you’ve nailed the look of the coolest influencer. 

Honestly, it feels like a conscious move to shop more sensibly and proving designers are putting a real focus on those timeless classics, notably tailoring. Sustainable brand, With Nothing Underneath, had this ethos in mind when they launched their version of the ultimate boyfriend shirt back in 2017. Founder Pip Durell, former Vogue stylist and Tatler editor, was inspired by masculine tailoring and the desire for clothing with a lifespan. The brand is now one of the most coveted in fashion circles. 

So whether you’re after crisp whites, bold hues or sartorial stripes, here’s an edit of beautiful button-downs, so you don’t need to steal one from the man in your life… and if in doubt, size up.

The products on this page have been selected by our editorial team, however, The Handbook may make a small commission on some products purchased through affiliate links.