I have been looking for a nice brown boot for awhile without much luck!  Ordered these after reading mostly amazing reviews and they were right.  They are a really nice leather that softens so nicely with wear, the look is classic with style and they so far seem like the quality one expects from the name "Timberland."  The ankle area does have some room (but I found it perfect for wearing skinny jeans and thicker socks) and they don't look strange or fall down so I have no issue with that.  My one hesitation when I first got them was the toe area, I usually like a squarish toe and hate the generic rounded/pointed toe that is so common in shoes these days.  These actually almost have a cowboy boot shape (around the foot) and while I hesitated at first, I love the way they look!  They are comfy, stylish and have very quickly made it into my favorite boots category.  I ordered a 7.5 and my toes seem to hit the right spot but would be interested in trying a 7 only because there seems some room in the foot  area and I can't tell if its the shape I am not used to or if it could be slightly smaller.  Honestly I think it is just the shape makes them roomier and more comfortable!