The go-to for effortlessly sleek menswear style? A black crew-neck t-shirt with black dress pants. Complement your getup with a pair of black slip-on sneakers for a truly modern mix. When it's one of those gloomy autumn afternoons, what better to cheer it up than a dapper getup like this one? This outfit illustrates that dressing stylishly as you pass the big five-oh is totally doable.