Who said you can't make a fashionable statement with an off-duty getup? That's easy in a bomber jacket and a red and black long sleeve shirt. Complement this look with a pair of beige canvas low top sneakers to bring an element of stylish effortlessness to your ensemble. As you can see, it's extremely easy to look on-trend and stay cozy come colder weather, all thanks to outfits like this one. And if we're talking casual outfit ideas for gentlemen in their 50s, this ensemble is a good look on most gents.