This combination of a crew-neck t-shirt and grey dress pants is on the line between dressy and casual. For something more on the smart end to finish off your ensemble, complement this outfit with a pair of black suede loafers. Dressing warmly is the trick to surviving below-freezing temps, but this outfit is a good illustration that this can also be done with style. Looking for style tips for gentlemen in their forties? This combo is great inspo.