For something on the off-duty end, test drive this combination of a henley shirt and grey jeans. Feeling inventive today? Spice up this ensemble by rocking black leather chelsea boots. During winter, when warmth is prized, it can be easy to settle for a less-than-stylish look in the name of convenience. This look, however, is a stark illustration that you can actually stay comfortable and remain equally stylish during winter. And if we're talking casual style tips for 30-something Millennial gentlemen, this combo is ideal.