My friend has these brownish, freckle looking markings around his ankles and is starting to get another similar markings in the back if his leg? It never goes away. What could thus be

This may. Be vascular. Capillaries will leak blood and stain the skin. I suggest you see your pcp.
Brown spots. These could just be pigmentation changes from age or sun but some spots come from poor circulation or diabetes. They could be from a fungus as well. Best to get them looked at to get a diagnosis and determine if any treatment is necessary.
Could be. Hemosiderin deposition, do the legs swell often? It likely is a benign process, like a staining of the skin, but, if there is any concern let them go to the doctor as we can't see the actual condition and hence are simply making an educated guess.