When you run in menswear circles, you tend to hear things you wouldn't normally hear in everyday conversation: Justification for an extremely expensive pair of loafers, for example. Or how this new hoodie, with the perfect cropped length and weighty French Terry fabric, is so different from all the others already hanging in your closet. It was in the midst of this type of conversation when I first heard the phrase, “the Ralph tuck”.

It was in reference to someone's artfully disheveled layered look: a washed waffle long-sleeve tee, under a flannel shirt, with a cool, cropped work jacket over it. But here's the key: the flannel was tucked in, but unbuttoned. The two sides of the placket barely kissing right at his waistline. It was unclear if Ralph Lauren—the man, the myth, the American style icon—was the originator of this particular style. But he was clearly a big fan.

You will see the designer wearing this look in multiple ways—on his ranch, like in the photo above but also on the streets of Manhattan and taking bows after one of his fashion shows. He also employed the look in various ad campaigns over the years. Why? Well, because it works.

It comes in handy when you want to wear your shirt casually, but leaving it out and untucked looks too unkempt. Perhaps you want a more cropped look to pair with your wide-leg pants. Maybe you're wearing a jacket that's shorter than the shirt's tail. Or maybe you just want a different look that's at once relaxed and casual, yet elegantly pulled-together. Whatever your reason, it's a move worth considering. Especially as we move into the transitional time between seasons. To help you get started, we've pulled together a few pairings to consider.