Like the title says, do you llike those sunny cloudless areas around Whiterun, or the deep snow areas like Winterhold? Or something else? Personally, I really enjoy walking through a forest while it's rainy and it's foggy out. Really aesthetically pleasing and the soundtrack just adds to the atmosphere.
I also like the gloomy, misty forests of Falkreath Hold however and the autumn forests of The Rift. I really enjoy walking through glaciers though, listening to the creaking and groaning of the ice, that sound effect was inredibly effective at immersing me in the environment.
Cold, grey, and snowy does it for me. That's one of the reasons I first fell for Daggerfall; the snowy desolation of an Illiac Bay winter called to me. It extends to just about any game, really.
And, unlike in reality, I don't have to shovel any of it.
I can never stray too long into the winterlands. I get quite enough ice and snow up here in Canada, thankee much! I love the perpetual green of Whiterun, the yellows and oranges of Riften. Soft sunlight ending in a night of auroras so beautiful they border on surreal - now that's my idea of a perfect day.
I was greeted by an aurora on my first night in Skyrim. I love walking in the Rift on a bright and sunny day. Oh, and I love the blizzards, too. Oh, and the thunderstorms! Wait, that means I love it all, huh?
Rainy days, clear nights, far away from the snow and ice. I hate the cold. I will visit the chillier looking areas on especially hot days, though. It's been over 100 degrees Fahrenheit here lately so I've been hanging out closer to Winterhold.
The Fall Forests around Riften are great when it's clear skies. A cloudy windy day on the Tundra near Whiterun is awesome. A misty day around Falkreath, or a Blizzard around Winterhold. I don't think there is one weather type that I don't find awesome. I get lost in all of them.