Unless you’re regressing to your school disco “Haribo-and-knee-slides” days, aboard an actual yacht or staring down the dregs of another Laphroaig during a profound existential crisis, chances are you’re a “shirt tucked in” kind of guy.

If button down shirts regularly feature in your sartorial circuit (and why wouldn’t they? They look damn fine with a vintage timepiece – just ask the Barrington Watchwinder gents) you’re probably well aware that an untucked shirt simply looks – well – schlubby. This rule, however, does not apply to a more casual t-shirt – or even a button down grandad collar shirt.

Tucked in T Shirt Fashion

Not so in days of yore, when a tucked in t-shirt was a slick style staple. Think James Dean, Marlon Brando and Steve McQueen. These masculine fashion icons looked stupidly cool – and a tucked in crew neck (with a motorcycle tank-full of attitude for good measure) was part of the package.

But in the decades since the 50s and 60s, a tucked in shirt became synonymous with neatness, with stuffiness, with “the man”, with an older generation – with grandfathers in elasticated braces… The shirts came out in a rebellion against the stifled, uniformity of weekday, nine-to-five workplace culture – and got bigger and baggier as rap and hip-hop culture made streetwear more voluminous and casually stylised.

Today’s increasingly relaxed professional spaces and growing self-employed, freelance market have further de-professionalised attire, making suits and ties ever rarer and welcoming casualwear into the office. With less and less reason to “dress up” and “tuck in” for work, the appeal of a tucked in t-shirt appears to be growing. Now destigmatised to a point, removed from its fussy and elderly connotations, the tucked in crew neck is making a comeback.

Man tucked tshirt

Seen on stylish personalities including the likes of David Beckham, David Gandy, Chance the Rapper and Virgil Abloh, the blend of slim cut jeans and a tucked in crew neck is enjoying a resurgence in popularity. With vintage 50s rebel-without-a-cause associations and a propensity for showing off a lean physique, there’s something about returning to the tuck which just makes sense.

Don’t have a flat stomach washboard abs? No problem. Either rock the look anyway or tuck your t-shirt in at the front, to one side of your belt buckle for a nod to the style, without baring your belly.

Where do you stand on tucking in shirts and t-shirts? Is an untucked button down ever acceptable? Do you like the vintage “tucked in t-shirt” look? Have your say below.