dan'l, shoot for the moon!
Yes, most people are at home in dark shades for Winter and light shades for Summer. It is a safe heuristic to follow. To spin it around, I would never really dream up of my own volition the idea of a light houndstooth in the cold season -- until I see the components built together as in Mr. Akamine's outfit. He has a refined sense of color and a big enough wardrobe that these things come naturally -- we (or I?) can only hit upon these combinations by slavish imitation. For instance, the scarf is a master stroke (just what should we call this color, anyway? "Clay"?), but I would never see that in a store and think, or even want, to buy it. The tone on tone on tone thing going on here is quite intriguing.
Anyway, that is a long way of saying, why not try for a Summer houndstooth? But by all means stick to your role model; you chose well.
You can register on the LL and it should walk you through it.