A grey sweatshirt and blue jeans are true menswear must-haves if you're picking out an off-duty wardrobe that matches up to the highest sartorial standards. Introduce white print canvas low top sneakers to this outfit and the whole look will come together. This is a fail-safe option for a cool look that will take you from winter to spring. This ensemble suggests how to keep slaying in casual dressing as a man over 40.