Make a denim jacket and black chinos your outfit choice for a comfy menswear style that's also pieced together nicely. Shake up this getup with a more sophisticated kind of footwear, like this pair of brown loafers. As the weather gets warmer, it's time to shed those bulky winter layers and opt for a look that's lighter, like this one here. Definitely a fail-safe option when it comes to outfit ideas for 30-something Millennial guys.