Well, I'll start by saying that I could not zip this boot up around my 151/2in. calf. Only could get the zipper up half way. Also, the boot runs very long. I take size seven in shoes and have regular-wide feet. These were 2inches too long for me.i ordered them in size 7wide. So order down a size or size and a half. And if you have 15in. Calves or bigger, these won't fit. Now, on the brighter side. They are a beautiful brown, super soft leather. Unlike other Tinberland boots I've tried, these have a rounded toe, which is nice. They are definitely not dress up boots. I hardly ever dress up and when I do it's low key. But these are even too casual/biker boot, for me. They are kind of manly looking, but definitely feminine enough for casual wear. If you are looking for a boot that is for casual wear, and maybe to wear with a jean or khaki skirt, then these are good. The buckle on top is strictly for looks and doesn't stretch the calf width. I have no idea about comfort when wearing these out because I'm returning them. But Timberland is supposed to be a comfort boot. Now, if you are looking for a similar boot, yet something that looks amazing whether dressed up or down, check out the Corso Como Gage Boot. They  also fit wider calves and semi-wide feet. I have a review on them under their sight on amazon. You will love them!