As mentioned before, finding the right footwear for rainy days can be difficult. Most guys opt for sneakers, Timberland-like boots, or boat shoes...none of which are both practical and stylish. I recommend the new "boat boots" that some designers have been coming out with recently. They are essentially high-top boat shoes that are waterproof, and perfect for casual outfits.
Pictured below are versions by Band of Outsiders x Sperry and Rogues Gallery.
Yours in style, Style Blogger.