I'm pretty sure I counted all that I have...so, 9 pairs.
Flat boots:
- Black leather cyberpunk Timberlands (These are what I wear the most. LOVE.)
- Black suede OTKs, can wear cuff up or down for a more piratey vibe
Sturdy heels between about 2" and 3":
- Deep purple faux suede with slouchy shaft and turndown cuff (I probably wear these second most often.)
- Brown steampunky suede with brass hardware and lace-up fronts
Then I have a pair each of red paisley tapestry and gold paisley tapestry boots with kitteny heels that are about 2.5".
For higher heels, I have gray leather ones with self-covered button detail all the way up the sides (these are like a cross between go-go boots and Victorian...sounds weird but it works), and sturdy heels though they are around 3" or a little more.
Finally, stiletto heels 3" - 3-1/2":
- Black suede with dark metal hardware ring details
- Black fishnet boots ("not safe for work")
All of mine are tall-shafted. I'm a petite hourglass and haven't had the patience to look for shorter-shafted boots, which I think would be a bit iffier looking as they'd chop up what little leg line I have.
What I see when I lay these out like this is that I like variety, once I've filled the requirement for having a great pair of go-to black leather boots that are COMFORTABLE *and interesting*. Normally I'm not big on flat shoes because my feet are small and I look better with some heel, but my Timberlands are so funky that they really work.
Also, I'm not a big fan of spiky stilettos in everyday wear for several reasons. Although my pair with the dark hardware (for instance) do look quite sexy and elegant, I don't *want* to exude "sexy" except when and where I feel it's appropriate. Date night, parties, occasions, yes, but not at work.
So, I would say to try lots of different styles because you never know what will totally pop on you that you might not normally consider, but also be true to yourself and only buy things that really DO fit your style, preferences, and needs. Personally, although I pay attention to what the trends are, I don't buy them if they aren't going to fit my lifestyle and personal style.
Finally, except for one pair that was only mildly on sale, these were acquired with major discounts. You can build a good collection for a lot less than retail!