This combo of a black leather bomber jacket and black skinny jeans is a safe and very stylish bet. For a more refined feel, introduce a pair of boots to the mix. As you can see here this getup is something you can totally wear as a man in his fifties.
Black Skinny Jeans with Boots Smart Casual Warm Weather Outfits For Men After 50
For an off-duty ensemble, try teaming a charcoal shawl cardigan with black skinny jeans — these pieces fit perfectly well together. Upgrade your look with a pair of boots. Wondering what you should wear as you head into your 50s? This pairing is a perfect example.