A black crew-neck t-shirt and navy ripped skinny jeans are wonderful menswear essentials that will integrate well within your off-duty styling rotation. Let's make a bit more effort now and complete this look with grey leather casual boots. Seeing as autumn is taking over, this outfit appears a savvy option for the time in between seasons. This combination should erase any doubts you had about dressing casually as a 50-year-old man.