For an effortlessly classic look, consider teaming a navy blazer with navy jeans — these two items go really well together. Brown suede chelsea boots are a fail-safe way to breathe a dash of refinement into your look. When leaves change color and fall starts to take over, you'll appreciate how ideal this outfit is for awkward transition weather. Interested in fashion for 50-year-old gentlemen? This outfit is worth saving to your inspiration folder.