A grey print crew-neck t-shirt and blue ripped jeans make for the ultimate casual getup for any modern gentleman. Change up this look with a more polished kind of footwear, like these black canvas slip-on sneakers. So if you're on the hunt for a look that's on-trend but also entirely season-appropriate, this one is great. This is a wonderful example of how to dress well as you work your way through your teenage years.