Boots I have acquired over the years:
1) Black leather, flat knee-high Franc Sarto's with round-toe, that fit snug on my calves. These are pull-on's. They are too snug to tuck in jeans. These are strictly for skirts. They are very comfy and work well with wool socks worn over tights.
TIPS: try them on with wool socks, if you intend to wear them in cold weather. Make sure there's enough room for socks. Consider whether you want to wear the boots with jeans or with skirts. Personally, I think looser-calved boots look kinda funny with skirts... but that could just be on me.
2) Wine leather, knee-high franc sarto boots with 1-1/2 inch heel and pointy-ish toes. These zip up. I can not wear them over jeans, but these are the most versatile of my boots.
TIP: wine is a great neutral to own! Wine goes with denim, grey, black, brown, winter-white. It mixes well with everything.
3) Brown Pleather (fake leather) pull-on knee-high boots with 2-inch wedge and snipped toe. These are more trendy, fun boots and beacuse they aren't real leather, I can wear them on days when I'm walking in slush and mess and not worry about ruining them. The wedge helps with stability on icy surfaces. But, they also aren't quite as warm as the leather boots.
TIP: consider the weather and how you will be wearing them.
4) Black suede pull-on knee-high boots (also franc sarto) with pointy toe and heel ... these have a sorta scrunch effect, but not overly so because they make my calves and ankles look the tiniest. These are saved for special occasions - go great with a LBD for a formal event. Because they are suede, I cannot wear them in slush and much though.
TIP: if you go to a lot of formal events in the colder months, it can be worthwhile to invest in a pair of dressy boots! Lots warmer than going out in strapless heels in the snow!
5) I also own a pair of black and a pair of brown ankle boots, for wearing with jeans and slacks. Actually, all of the above boots can be worn under loose-fitting jeans and slacks too, for extra warmth.
6) UGGs, for the snowiest days when only UGGs make sense. I have three pairs in varying heights and colors.
What I still need: a pair of boots that I can tuck skinny jeans into... but first need the skinny jeans.