The difficulty with mixing dressy and casual elements is finding items in each category that work well together. In this case, a gingham check shirt with a tie in an earthy tone helps bridge the gap between the dressy look of a dress shirt, tie, and sport coat, and the casual look of a drawstring hoodie. This is very well done.
Men's Fun Classic Style | Vintage Mens Fashion Trend Inspiration | Colorful socks | Stylish shoes | Tweed, Plaid Blue Slacks | groomsman ideas | Madmen | Brooks Brothers Preppy Fun Style
don't know if it's the black and white, the handsome men, or their ensembles but this picture is working for me.