I am not entirely sure that you can call the fall and winter here in Portland anything other than an eight month drizzle, peppered with momentary breaks in the cloud cover. When it started pouring earlier this week I was faced with the unfortunate dilemma of either being late to work due to trying to unearth my Sperry rain boots (just like the boots in the second row, far right) or having wet shoes and wet toes. I went with the wet toes and early arrival but literally had to prop up a sad pair of flats on a colleague's heater for a good half-day before they dried out into stiff mud-caked sorry-excuses for D'orsay flats. Ick.
The 8-10 months of rain here, especially for a walk-commuter like me is made 100 times better by a good pair of rain boots that aren't just hideous, shiny, and foot-sweat-producers. I finally invested in some good waterproof footwear last year when I was commuting by foot and under an umbrella. As I suspected, a plain pair of unlined boots is entirely irrelevant as the weather gets colder. You can't rely on rubber and a pair of athletic socks to protect your toes in bad temps. Lining is everything!
I am obsessed with the options above and really want to update my rain wardrobe, especially with those Hunter ballet flats and Loeffler Randal stylish boots. Now that I have a nice rain coat and a cute patterned umbrella, my feet are an eye-sore on most occasions. I seriously go through my walk-to-work shoes like they're cardboard. Putting almost three miles in on a daily basis on a sidewalk in the pouring rain is never good for any shoe, and most shoes that are built to withstand that abuse are really hideous. Time for a stylish update.