My favorite season to buy clothes for is Spring and Fall. I hate summer clothes (gasp I know) because I don't like the bright colours, short hemlines, and flip flops. I like Spring and Fall because you get to wear dark colours, beautiful coats, scarves and boots (because it's always raining in Vancouver).
I have about 4 pairs of leather/pleather boots, 1 seude and 2 UGGs. But my top favorite 3 pairs are these:
From Aldo - a light weight over the knee 3 inch heel boot that's warm inside
From Aldo - the popular slouchy style that pretty much every girl has
From Calvin Klein - the Mayson Nappa over the knee boots. This one is made with real leather and it bunches up at the top to create a sleek but unique look. Sorry, I couldn't find a bigger stock photo of the boots.
I don't have any designer boots yet. I don't know how worth it they would be for me and my lazy lifestyle. I prefer flat boots more (I live in flats). But it seems like all the pretty designer boots have a high heel.