As you can see here, looking effortlessly sleek doesn't take that much effort. Choose a brown double breasted blazer and navy jeans and you'll look incredibly stylish. For something more on the classy end to finish your outfit, add a pair of dark brown suede loafers to the equation. This one is a nice choice when it comes to picking out a killer outfit for weird transition weather. Definitely a never-failing option if we're talking fashion tips for men in their fifties.