These are a true 8.5 medium. They are wide through the toe which makes them very comfortable for walking. They are a bit shorter than I expected--not as tall as riding boots, but clearly taller than a bootie. They are around the widest part of my calf. The leather is nice and soft so they will stretch to fit a larger sock. The color is perfect and very close to that pictured if one's monitor isn't turned up to bright. I primarily bought them to wear when visiting Europe this winter and think they will be great for this purpose with their wide toe box and low heel. If you buy them to wear with thick socks, consider buying a 1/2 size larger.

Update: After wearing these incessantly for a week or so, I suggest you don't buy a larger size. They stretch out nicely. These are one of the most comfortable pair of boots I've ever owned and highly recommend them. I'm planning on wearing them all over Italy soon.