Make a black leather bomber jacket and navy and green plaid chinos your outfit choice for killer menswear style. On the shoe front, go for something on the laid-back end of the spectrum and round off this look with a pair of black leather work boots. Keep this look in your head come warmer weather, and we guarantee you'll save a ton of time racking your brain for what to wear on more than one occasion. Casual getups for stylish gentlemen in their 30s aren't actually that hard, as you see.