Untucking Your Shirt
Credit: Courtesy Untuckit

A casually untucked button-down walks the line between informality and sloppiness, but it's getting easier to stay on the right side thanks to the designers trimming shirttails in the anticipation of their customers' decision to hang loose. Chris Riccobono, founder of shirtmaker UNTUCKit, which specializes in shorter collared shirts, conducted market research before rolling out his first line and found that men are specific and consistent about their untucking preferences.

"An overwhelming majority of those we surveyed preferred the untucked shirt to be long enough to comfortably cover the buckle, but short enough to leave a small portion of the pant pocket exposed," says Riccobono. "Once you cover the pant pocket, you didn't have to get much longer before people felt it started to look very sloppy."

Tailoring is also key to the look, as many boxier American cuts look oddly tent-like when not pulled down. Riccobono found that he had to make slightly tighter shirts in order for men to feel comfortable leaving them loose. His experience tracks with what Alex Faherty, co-founder with his brother of the beachwear company Faherty Brand, found while making comfortable shirts for surfers and swimmers.

"If the shirt fits comfortably in the shoulders and chest, it will fall right where you want it in relation to your waistline – which should be no more than three inches below the top of your pants," Faherty explains.

Faherty Brand's textured fabrics invite rolled-up sleeves for the perfect weekend BBQ look while UNTUCKit offers a tie-free business casual take on the button-down with microchecks and plaids. They pair better jeans for the evening out and are a bit slimmer in the front, allowing you to look put together without cinching in your shirt. [Untuck flannels from $89; untuckit.com]