If you're looking for a casual street style yet seriously stylish outfit, pair a long sleeve henley shirt with navy denim overalls. Dark brown casual boots will give a hint of elegance to an otherwise standard outfit. This outfit demonstrates that as a man in his fifties, you still have a wide range of style options.
For seriously stylish menswear style without the need to sacrifice on functionality, we like this combo of a long sleeve henley shirt and blue jeans. Play up the dressiness of your look a bit by wearing dark brown casual boots. When it comes to casual fashion for 50-year-old gents, this getup looks cool on most.