This combination of a beige plaid blazer and a blue denim shirt strikes the perfect balance between dressy and casual. On the shoe front, go for something on the laid-back end of the spectrum by finishing off with brown leather boat shoes. As you can see here, it's extremely easy to look seriously stylish and stay comfy when chillier weather arrives, thanks to this getup. Interested in fashion tips for 20-something men? This getup is pretty inspiring.