This relaxed pairing of a grey herringbone wool blazer and a grey print sweatshirt is extremely easy to put together without a second thought, helping you look dapper and prepared for anything without spending a ton of time rummaging through your closet. If you're puzzled as to how to round off, complement this outfit with a pair of black canvas slip-on sneakers. So as you can see, it's extremely easy to look awesome and stay comfy when cooler weather hits, thanks to this look.