A black leather biker jacket and white and black houndstooth chinos are amazing menswear staples that will integrate nicely within your off-duty styling lineup. To give this look a more casual feel, why not complete your look with black and white athletic shoes? When temps are getting lower and autumn is settling in, you'll appreciate how perfect this ensemble is for weird transition weather. This combination is a great inspiration to anyone who had doubts about sporting casual outfits as a middle-aged gentleman.