Wear a grey plaid double breasted blazer and black dress pants and you'll be the epitome of classy men's style. A pair of black leather derby shoes will give a playful feel to your outfit. So so as you can see, it's a seriously stylish, not to mention spring-appropriate, look to have in your transitional rotation. If you're wondering what you should wear as a gent in his 50s, this outfit gives a good idea.