OTK boots at O-30

I am going to try to pull off over the knee boots at 32. And I am a teacher of college-age students, so that will make it extra hard to:
a) not look like a Skankarella prostitute,
b) not like I am trying way too hard, and
c) not elicit sour looks from real faculty/advisers/chairs

What I do have working for me is that my West Texas town is at least five years ago, so anything post-Ugg is still "fresh."

I hope the ones I ordered aren't ugly in real life. They come Saturday. They are at a shipping facility in Dallas right now. I just checked. In my brain, I have them on as pants, wearing them with dresses. They will never be worn with skinny jeans. No. The ones that are coming have a 14" shaft/opening, which is what I have. Here's hoping. Wish: Please, please do not look cheap, even though I stingily bought you for $49 + gift card.

UPDATE: Oo they came later that night! Here they are:

What I'm wearing:

Dress: F21

Cardigan: Macy's cashmere from Xmas sale '09

Boots: Steve Madden

I thought they'd be a bit longer/taller. I am not sure why they are a bit loose in the back (not tight on your thighs at all) but my calf and thigh measurements are about the same. I wonder if they have to meet/exceed the hemline of your dress to look really great? I am pleased with them. I will need to play around this weekend and figure out how to wear them.

The front-facing pics are bit misleading on snugness. The tops are a bit baggy (14" tops), but when you sit down they are ok. Not sure. Hmm. To alter or not to alter...?


UPDATE 01/21:
A few days later, I am really pleased with this purchase and I think the boots have a lot of potential. They aren't 100% perfect (a little loose at the top) but reading other blogs and seeing other pictures of people wearing similar styles has been inspiring. I almost went with more expensive pairs, and I agonized about buying shoes I "didn't need" for several days. For $50 though, I am really pleased with this purchase.

I like that they are made of a suede-like material instead of leather (or worse: fake leather) which would have increased the hooker potential tenfold. The material doesn't make the boots shout at passerbys; the materials let the boots act as tights/pants in a way, which was my original goal! I am really happy with these! I will be experimenting with different outfits around the house this weekend. I think they need tights in most cases.