There's nothing better than a leg-lengthening heeled boot, some of which can be very comfortable, but the true workhorses of my fall/winter wardrobe are flat boots, boots with a bit of a chunky heel that I can wear all day, pain-free. Target has managed to make available 5 such pairs of boots that have me wishing I could own them all. I can hardly justify purchasing yet another pair of boots but for those of you who are in the market for a new pair, keep reading to see these 5 beauties under $50.

1. Mossimo Supply Co. 'Kahnilyn' Buckle Boots in Grey, $29.99

Can you guess which of the rain boots below costs $45 more than the other? Click either image to find out!