These boots look great over a pair of jeans or leggings- they come just over the knee but can be folded down. They also can be worn with a skirt for a going out look, however, probably not best suited for a conservative office environment. I am really happy with the quality of the leather, heel -which is study, and shape. In terms of comfort, I give these a four out of five. I can wear them all day long with minimal discomfort until later on or the next day. I am a size 10 wide, and find these to have extra room in the ankle area. Ever since I started wearing these, I have had pain in my left ankle and shin- this could be from a previous injury but I have noticed the lack of support in the ankle area exacerbates the pain. For this reason, I wear two pairs of socks to provide support. Overall, these are a great looking pair of boots, and even despite the lack of support, I am happy with them.