Fashionable and practical, this relaxed combination of a gilet and a short sleeve shirt will provide you with variety. Get a bit experimental in the footwear department and add a pair of navy leather high top sneakers to your ensemble. As you can see, it's extremely easy to look sharp and stay comfy when chillier weather comes, thanks to this outfit. This is a great illustration of how to dress well and look good as you work your way through your teenage years.