If it's ease and practicality that you're seeking in an outfit, dress in an orange hoodie and charcoal jeans. If not sure about what to wear on the footwear front, stick to a pair of black and white low top sneakers. This look is a viable pick if you're picking out a neat outfit that transitions easily into fall. Those who wonder how to pull off cool casual style as you move into your 30s, you have your answer.