It hadn't been too long ago that Jon's wardrobe consisted entirely of black, though that had nothing to do with his clothing choices. The introduction of color (especially the color red) into his wardrobe is almost entirely down to Sansa's influence, especially when she made him something and then just expected him to wear it. He's learned not to argue with Sansa.

Besides, he's left that part of his life behind, so he should start dressing like he's moved on.

"I suppose I am. I can't decide which one I like better, so I'm looking for opinions."