For a casual and cool getup, consider teaming a crew-neck t-shirt with charcoal ripped jeans — these pieces play nicely together. Add grey high top sneakers to the equation and the whole outfit will come together really well. This one is an exciting idea if you're figuring out a neat look that will take you from summer to fall. If you often wonder how to dress age-appropriately while looking fashionable, this ensemble is a safe option.