Consider pairing a hot pink blazer with a dress shirt if you're aiming for a clean-cut, trendy look. Add a pair of tan leather double monks to your outfit and you're all done and looking killer. When leaves turn yellow and red and autumn settles in, you'll appreciate how perfect this getup is for weird transition weather. This ensemble demonstrates that figuring out how to dress well as you slip into your 60s is not that daunting a task.