If you feel more confident in practical clothes, you'll like this laid-back combination of a grey bomber jacket and a henley shirt. Introduce a pair of white leather low top sneakers to the equation for maximum fashion effect. Keep this outfit in your head when spring sets it, and rest assured, you'll save a ton of time getting dressed on more than one occasion. Think you can't pull off edgy casual style as you reach your 50s? This combo is solid proof of otherwise.