Boots: Greatest thing about fall since pumpkin spice lattes

Every fall, without fail, I notice the falling temperatures and get depressed--that first night when I need to grab a cardigan to go over my sundress just kills me. But then, every fall, I think about tall leather boots and I get happy again.

I'm determined that this will be the year I get the "go anywhere, matches anything" black boot, and Nine West has two great options.
The Cookin' Boot, $99, has all the makings of a classic--but is it too boring? I like the modest heel and streamlined calf, but I can't help my love for buckles and straps.
The Tierney boot, $169, is just a touch more exciting, a little more cowgirl. But I do really like that it has a half-zip on the side, as my current boots have lost their shape and slouch more than Katie Holmes in her Joey Potter days. A zipper would, I assume, help the boots keep their structure.

Then there's the side of me that says, "Screw the practical basic! I want the showstopper special occasion boots!"
Just the words "blue suede" give me shivers, so I'm just about shaking thinking about the Alexa boots, $179. I love the cuff that can be flipped up to cover the knee--it's very season 1 Serena Van der Woodson (you know, when she still wore clothes that covered her ass). But to be honest, I have no idea what I would wear with these. I don't think jeans would look right, with the blue on blue, and a skirt might compete for attention. Maybe a snug, rugby-striped sweater dress... or maybe something in a pale shade of yellow? Or grey? Or a leather jacket with studs that mimic the ones on the cuff? I'm stumped, but am dying to take on the challenge.