For a casual ensemble, try teaming a black leather biker jacket with navy jeans — these items play really well together. And if you need to immediately ramp up your outfit with a pair of shoes, add beige suede casual boots to the mix. It's is an obvious choice if you're scouting for a knockout outfit that will take you from summer to fall. Think it's hard for guys in their 40s to nail cool casual outfits? This combination will prove you wrong.