A light blue vertical striped dress shirt and navy jeans work together beautifully. Get a bit experimental in the shoe department and lift up your look by slipping into black suede loafers. As you can see here, it's super easy to look on-trend and stay warm when chillier weather arrives, thanks to this look. If you frequently wonder how to dress appropriately for your age but also look fashionable, this combo is a surefire option.