For a safe smart option, you can never go wrong with this pairing of a navy blazer and a light blue long sleeve shirt. Complement your outfit with grey athletic shoes to inject a dose of stylish effortlessness into this look. So if you're looking for an ensemble that's stylish but also feels entirely season-appropriate, you found it. This ensemble should inspire anyone who wasn't sure about donning casual outfits as a gent over 40.