A navy long sleeve shirt and blue jeans are the kind of a fail-safe off-duty combination that you so awfully need when you have no extra time. To add some extra fanciness to this getup, add a pair of dark brown leather loafers to the mix. When it comes to dressing for transitional weather, nothing beats a neat getup that transitions easily between seasons. So if you're hunting for a modern yet age-appropriate ensemble, this one fits the bill.