Sporting something as basic as this street style combo of a biker jacket and black skinny jeans will set you apart in a good way. Rounding off with black leather low top sneakers is the most effective way to bring an added dose of style to your ensemble. If you feel uninspired by your transitional weather fashion options, this outfit just might be the inspo you are searching for. Think you can't pull off cool casual style as you move into your 50s? This combination should prove you otherwise.