You can be sure you'll look handsome and smart in a dark brown plaid blazer and a light blue dress shirt. Brown suede tassel loafers will add a different twist to your outfit. This ensemble is an exciting choice when it comes to a knockout outfit that transitions easily into fall. As you step into your 30s, you probably want to start dressing in a classier manner. In this case, looks like this are a goofproof option.