For a cool and casual ensemble, opt for a black leather biker jacket and navy jeans — these items play nicely together. Black leather chelsea boots are guaranteed to give an element of elegance to this outfit. We're loving how perfect this outfit is when cooler weather hits. Those who are dubious whether you can still pull off cool casual dressing as you age into your 50s, this getup should answer your question.
Try teaming an olive overcoat with navy jeans for an off-duty getup with a twist. Take a classic approach with footwear and complete this outfit with a pair of black leather chelsea boots. If it's one of those dreary fall days, what better to brighten things up than a dapper ensemble like this one? Perfect if you're after some amazingly inspiring relaxed style for middle-aged gentlemen.
If you're on the lookout for a modern casual but also stylish ensemble, consider teaming a dark brown leather military jacket with navy jeans. If you need to immediately ramp up your look with one piece, why not add a pair of black leather chelsea boots to your look? We promise this look is the answer to all of your transitional wear woes. Think 50-something gentlemen can't pull off modern off-duty dressing? This combination is hard proof of otherwise.