A navy print bomber jacket and a black crew-neck t-shirt are a cool outfit to add to your casual styling rotation. For something more on the daring side to round off your getup, introduce a pair of black and white canvas high top sneakers to the mix. This one is an exciting idea if you're on a mission for a knockout outfit that transitions easily into fall. Wondering how to nail casual outfits as you mature into your 30s? This combo is the perfect answer.