A grey windbreaker and navy jeans are a great pairing worth incorporating into your current styling repertoire. Infuse a touch of stylish casualness into this outfit by finishing off with a pair of charcoal canvas high top sneakers. As you can see, it's super easy to look amazing and stay snug come fall, all thanks to combinations like this one. When it comes to casual fashion for 30-something Millennial gentlemen, this look looks great on most gentlemen.