An olive parka and a denim shirt? This is easily a wearable getup that anyone can sport on a daily basis. Make your look slightly more elegant by finishing with a pair of dark brown leather casual boots. As you can see, it's super easy to look on-trend and stay toasty when chillier weather hits, all thanks to looks like this one. When it comes to casual outfit ideas for gents over 50, this combo looks cool on most.