A crew-neck t-shirt and navy skinny jeans are among the fundamental items in any gent's properly balanced casual collection. Add a sleeker twist to your outfit by slipping into grey leather casual boots. As you can see here, it's super easy to look stylish and stay comfortable come chillier days, all thanks to getups like this one. This getup should erase any doubts you had about wearing casual clothes as an over-50 guy.