Fresh out of college, when I first started working in New York, I picked up a really great pair of Tory Burch Winnie rain boots. I found them at a sample sale which helped to justify the splurge, but as much as I love them, they’re not really the “ideal” rain boot. If truth be told, they’re rather difficult to slip on and off being that they’re rubber riding boots that actually hit on my knee, and wearing them all day indoors is like spending the day with your legs in a sauna — which does make them amazing for keeping warm on a snowy day. At the time I was a big believer in the whole “beauty is pain” mentality (I also would run around NYC in high heels all day, every day), but now I’ve not only come to embrace more comfortable footwear for long days on my feet, but I’ve also realized rain boots can still be super chic and also functional. This pair looks sharp even on drizzly days, plus they are so much more practical.