For a fail-safe semi-casual option, you can always rely on this combo of a polo and grey dress pants. If you wish to effortlessly dial down your look with one single piece, complete this getup with a pair of white canvas low top sneakers. A vivid example of practical fashion, this look must be in your front hall closet when subzero temps hit. Wondering what you should wear as you work your way through your 20s? This pairing is an amazing example.