I bought these in the light brown. When I got these in the mail I immediately tried them on. They are extremely comfortable! I had on long flared jeans and they looked awesome underneath. I then rolled my pants up to my knees to see how they would look with a skirt or capri's... and they looked sort of stupid. I mean, they are mid-calf height boots... and those never look good on me with skirts or shorts. I then tried them on with skinny jeans and they looked amazing! They are slightly wide at the opening, so they don't hug your calf. I think they would look super cute with some light wash shinny jeans and a plaid button-up. Very wintry looking. I have a few pairs of Frye boots and they don't compare to these as far as comfort goes. These boots have some cushion in the heel area. Definitely a nice boot!