What type of boots are these and when are they worn?

My shoe game is wack. Only recently became fashion conscious - started out with a good fitting pair of dark wash jeans and I'd like to move on to footwear.

I came across this picture: http://i.imgur.com/lmj8KPK.jpg And thought his boots looked pretty kewl.

I was just wondering the name of the style and possibly even a guess at the brand. I also would like to know how versatile they are and what types of clothes you feel they should typically be worn with.

These may not even be the best footwear to start out with - they just stuck out to me and I'd like to wear something besides my granola NorthFace Trail Runners (badass functionality though) on a casual night out.