For an ensemble that's pared-down but can be modified in a myriad of different ways, consider teaming a bomber jacket with a black gilet. To give this ensemble a dressier twist, complete your look with a pair of dark brown leather chelsea boots. This ensemble is a really wonderful option, especially for autumn, when the temps are dropping. As you're transitioning from your 20s to your 30s, you want to start dressing maturely. That's when looks like this are a fail-safe option.