Dress in a v-neck t-shirt and navy jeans for a fuss-free outfit that's also pulled together nicely. If you need to instantly up the style ante of your outfit with a pair of shoes, complete this ensemble with a pair of desert boots. A stylish summer-to-fall transition outfit like this one makes it super easy to welcome the new season. Perfect to tell people that even as a gent in his twenties you're confident enough to make your own fashion choices.