If you don't take fashion lightly, go for a casually neat ensemble in a white suit and a tobacco polo. White and black leather chelsea boots serve as the glue that will bring your look together. So so as you can see, it's a knockout, not to mention season-appropriate, combo to keep in your transeasonal wardrobe. This combo demonstrates that figuring out how to dress stylishly as you get into your 50s is not that daunting a task.