When I was in high school, I swore to myself that I would never wear rain boots. I thought that they were hideous. However, now that I'm out of the car-culture suburbs and in Manhattan, I've learned the importance of a good pair of rain boots. Actually, I have learned the importance of good shoes in general. I walk about five miles a day on average, and so I need a good pair of shoes for every occasion.
My wool lined rain boots have saved my life these past few days with the hurricane and freak blizzard. One mistake that I did make though: if you know that you will be using your rain boots frequently, then get a neutral color. I end up revolving every outfit I wear around my bright green boots, and quite honestly I'm getting tired of it.
But if you know that your rain boots are a once in a while affair, then make them pop! Show off those boots! It's fun to center an outfit around one piece... except when it's been the same piece for over two weeks.