If you put functionality above all, this street style pairing of a white and blue vertical striped dress shirt and blue ripped jeans is your go-to. And if you want to instantly polish off your ensemble with a pair of shoes, add beige suede chelsea boots to the equation. This one is a great option when it comes to putting together a standout outfit for transitional weather. Outfit inspo like this will help you remain enviously fashionable as you go through your 20s.