For an outfit that's pared-down but can be smartened up or dressed down in plenty of different ways, opt for a navy puffer jacket and light blue jeans. Complete your getup with olive canvas low top sneakers to shake things up. So if you're on the hunt for a comfortable transition look, this one fits the bill. Well into your 30s, you want to start dressing more professionally. In this case, getups like this are a tested option.