If the setting permits a casual ensemble, you can dress in a navy and white vertical striped long sleeve shirt and khaki chinos. Change up this ensemble with a more sophisticated kind of shoes, like these dark brown suede desert boots. Seeing as it is getting colder with each day, this outfit appears a great option for the time in between seasons. Those who are curious whether you can still wear edgy off-duty dressing after 40, you have your answer.