Dress in a white and navy crew-neck t-shirt and jeans, if you prefer to dress for comfort without looking like a hobo to look stylish. Get a little creative on the shoe front and smarten up your outfit by rocking dark brown leather desert boots. This one is a good option when it comes to figuring out a killer look for unpredictable fall weather. This pairing shows that dressing appropriately for your age and looking fashionable are not mutually exclusive things.