A navy henley sweater and beige skinny jeans are indispensable menswear pieces to have in your casual box. To add a bit of flair to this look, complement your ensemble with chelsea boots. When it comes to dressing for fall, nothing beats a killer getup that can take you from season to season. Guys who are curious how to sport semi-casual outfits as you move through your 20s, this ensemble should answer your question.