The ‘Cuban’ part refers to the shirt’s open collar, which makes it ideal for putting some air on your chest. In addition to this, most Cuban collar shirts also feature a fairly boxy fit, straight hem and button-up front.This shirt is a must-have for most guys, but there are a few considerations to be made. “Approach with caution,” warns personal stylist Daniel Johnson. “This style is not for the thicker necked bloke. Make sure to get it right on the body too, or it’ll look like a pyjama top.