I’ve always loved chelsea boots. I’ve been wearing one pair religiously since college and I absolutely love sliding them on. Men’s chelsea boots are perfect with jeans. Most just slip on and they look great. The image below is basically what you’re looking for. A nice men’s boot with a round toe and leather sole. Don’t skimp on price. Buy the best quality you can afford and if taken care of (find a cobbler!) they will last a long time!