To look like a contemporary gentleman, pair a waistcoat with a white and red dress shirt. Add brown leather derby shoes to the mix to make a traditional look feel suddenly fresh. So as you can see, it's extremely easy to look awesome and stay comfortable when fall arrives, all thanks to ensembles like this one. As a 30-year-old guy, you probably want to start dressing like a grown-up. That's when inspiration like this is very useful.