Fits as expected, my feet are smaller (size 7) and Sperry Top Sider is one of the few quality brands that make true to size shoes. The grip is a bit slippery so be aware of this if you work anywhere where the surfaces are slippery or dusty (I run a pizzeria and have had a few slips in these boots). I was expecting that these are neither athletic shoes nor skateboarding shoes but pumps designed for a preppy and lifestyle look. However, these are comfortable shoes and I'm on my feet about 8 hours a day, 4 days a week. To pair them with an outfit, I recommend wearing them with darker skinny jeans, a lighter-colored belt and a fitted shirt. Depending on the climate, you can wear it with a cardigan or swap your skinny jeans for darker shorts.