To achieve a casual look with a modern twist, consider wearing a bomber jacket and a short sleeve shirt. Our favorite of a multitude of ways to finish off this outfit is a pair of tan suede casual boots. If it's one of those dull autumn days, what better to cheer it up than a stylish ensemble like this one? This combo shows that as a guy over 50, you still have a wide array of dressing options.
This casual pairing of a bomber jacket and a short sleeve shirt is a never-failing option when you need to look dapper but have zero time. Balance your outfit with a dressier kind of shoes, like this pair of burgundy leather casual boots. An amazing transition outfit like this one makes it super easy to embrace the new season. Off-duty looks for 50-something gentlemen aren't actually that hard, as you see.
If you feel more confident in comfortable clothes, you'll like this seriously stylish pairing of a bomber jacket and a short sleeve shirt. Dark brown suede desert boots are a stylish complement to your look. Seeing as the weather is getting chillier every day, this outfit seems a viable choice for in between seasons. This pairing should prompt anyone who was doubtful about wearing casual clothing well into your 50s.
This off-duty combo of a bomber jacket and a short sleeve shirt can only be described as devastatingly sharp. Want to go easy on the shoe front? Throw in blue athletic shoes for the day. This getup is a viable pick if you're piecing together a knockout summer-to-fall look. Sartorial inspiration like this will help you stay incredibly fashionable even after 50.