This pairing of a denim jacket and black skinny jeans is a nice ensemble for off duty. When not sure as to what to wear when it comes to shoes, go with a pair of low top sneakers. It's a smart pick when it comes to picking out a standout outfit for awkward transition weather. This combo illustrates that figuring out how to dress well as a guy in his 50s is totally doable.
A denim jacket and white chinos worn together are a wonderful match. For something more on the casual and cool end to complement your look, add low top sneakers to the equation. This getup is everything for when temps are falling and fall is in full swing. If you often wonder how to dress appropriately for your age but also look stylish, this getup is a vivid example.