I think you look fine either way, honestly. No better time than cold weather time to grow out your beard, haha, especially if it fills in well like yours does. I think you'd look best somewhere in between though. You almost have kind of a baby face in your shaved picture, in a good way, with a cleft chin/dimple. I personally like facial hair, but on you, too much of it covers some of those good attributes. So *I* think you'd look best with some kind of in between look, a little bit of scruff. Like the week-or-two-no-shave look, haha, where you have the scruffy rugged look, but it's not so long or filled in yet that your face isn't showing through a little. Does that make sense? That's just what I see in my head based on the stubble I see coming in in your shaved picture, lol.
How long did it take you to grow your beard out that long? It's rather impressive. =D