This casual combo of an olive bomber jacket and a hoodie is ideal when you want to go about your day with confidence in your ensemble. In the shoe department, go for something on the casual end of the spectrum and complete this look with a pair of white canvas high top sneakers. When it comes to dressing for weird transition weather, nothing beats a cool look that transitions easily between seasons. If you often wonder how to dress your age, this outfit is a fail-safe option.