Recently, a commercial has been airing ad nasuem extolling an invention that took years to perfect–an untucked shirt.

The shirt company, UNTUCKit, claims to have perfected a menswear shirt designed to be worn untucked.

We hate to break it to this so-called breakthrough, but shirts meant to tuck or untuck are about deciphering a few style edicts, not a specific brand. (And hello? Southern guys have been untucking a’la Nashville music industry insiders for decades.)

What are the rules on tuck or untuck? We share below.

Old vs New Rules

The old school rule of tuck versus untuck went something like this: a short, even hems like that seen on polos and T-shirts are made to be worn untucked while uneven hem with “tails” in the front or back, meeting on the sides by your hips, is meant to be tucked.

The new school rule? Untucked is about the entire outfit, fabric of shirt and level of dressiness for the occasion you are wearing the shirt. So even if your shirt has tails, it can (sometimes) be untucked.

Always Untucked

Shirts that should always be worn untucked? Hawaiian and other vacation shirts, henley shirts, short sleeved button-fronted sport shirts and T-shirts should always be worn untucked.

Tucking any of these shirts in will scream AARP-tourist-nerd style instead of laid back cool.

One caveat on these untucked only styles? If the shirt is not at least as long as your belt buckle it is too short. Ditch it and opt for a longer length.

Conversely, a shirt that falls below your crotch is too long. The sweet spot is below the hipbone and above the top of the leg.



Denim and plaid and flannel. All perfect elements for an untucked look.

Outfit for untuck

If your shirt has “tails” how do you know whether to tuck or not?  It all depends on the surrounding clothing.

If you are wearing denim, boots, flat cotton chino style pants with tennis shoes, deck shoes or any uber casual footwear, your shirt may work untucked.

A slim denim shirt that hits below the belt and above the crotch is a perfect untuck shirt.

Shirts that are made of flannel, denim or chambray are also untuck worthy.

Dress pants, pleated pants and any style of dress shoe deems the shirt must be tucked. Any shirt worn with a tie must also be tucked. Untucking with these elements doesn’t equal laid back cool. It equals sloppy.

Beware the Billow

Shirts with a slim or modern fit look best untucked. If your shirt is oversized you risk looking heavier than you actually are if worn untucked.

Likewise pants that have pleats or are roomy in the thigh can create an oversized look when an untucked shirt is added to the mix.

Opt for slim pants that give a more streamlined silhouette.