I live in the tropics, so it isn't so much summer and winter as "loads of rain that will attack you on your way home" and "desert drought with merciless sunshine".
For the rainy season, I love sticky rice porridges and sticky rice pudding. When they're hot, of course. Here's a recipe for the chocolate rice porridge:
1 cup glutinous rice (which, contrary to its name, does NOT contain any gluten!) (the rice grains look completely opaque white, unlike ordinary rice which is somewhat translucent or grayish)
2.5 cups water for boiling the rice in
1/2 cup unsweetened cocoa powder, for adding to the rice porridge when it's cooked
1/2 cup white sugar, for sweetening the chocolate rice porridge when it's cooked
I've been trying to figure out a way to make a porridge out of the rice pudding recipe that I know, which is glutinous rice, steamed, then added to a syrup made out of ginger steeped in coconut milk (remove the ginger chunks) and the rawest brown sugar possible--I think I can just substitute blackstrap molasses for this.
How could I forget: soy curd and brown sugar syrup with sago pearls. It's a street food that I'd even have that when it's hot.
Now for when it's hot!
Hmm... shaved ice. There's another local recipe that adds a lot to it: caramel flan pieces, a scoop of ice cream, beans, sugar syrup, and gelatine pieces. There are also shaves ice desserts with syrup-cooked plantains (or cooking bananas) and shaved ice with milk and corn. Anything iced or frozen or chilly is fine by me, though. I'm not usually fond of coconut, but coconut water or coconut milk can be great with pureed avocado.