"I learned a lot about 'fashion' (re how to dress myself) from my father. While he didn’t have a deep closet, he always seemed to wear just the right thing for the right occasion, especially inclement weather. One of the few things from his collection that I could never get down with though, was galoshes (aka gumshoes, rubbers, or overshoes, whatever you want to call them).
In theory, galoshes make a lot of sense: Put them on over some nice shoes, get wet, take them off, shoes stay dry. But in practice, they were absolute murder to put on and take off and provide zero traction on slippery terrain. Since wearing Wellingtons around the office is a little much and packing an extra pair of shoes isn’t up for discussion, what’s a boy to do on a rainy day?
After a long search, I discovered these Hunter Original Refined Waterproof Chelsea Boots. They look enough like (stylish) regular shoes, they slip on and off with ease (which is great for not tracking in any mud) and most importantly they keep everything nice and dry from the ankle on down." —John Mihaly
Get it from Nordstrom for $155 (available in sizes 7-13).