Reunion dinner outfit! Need help choosing!

I know that it doesn't actually matter what I wear to my reunion.

In fact, it rarely matters what I wear ever. I'm actually rather vain, although it's not always evident. Sometimes I leave the house for hours looking like I was dressed in the dark by a mean-spirited chimpanzee.

You should see what I wore to volunteer at school yesterday, which was culottes, because it very warm out, and then my new Sanita clogs which currently feel better with socks on. So.

My son was all, "Uh, do you like those pants?" He did not. I told them they'd look better without the black socks.

You wouldn't know it by some of the things I am willing to be seen in in public, but I love clothes. And shoes. And boots. It's no secret I have a boot problem.

So. With all that said, which outfit do you like for my reunion dinner? It's at a bar/restaurant on Franklin Street. The weather is going to be maybe 50s-ish. Or 75. Or down to 32. Because who actually knows anymore.

The suggested dress for dinner is something along the lines of jeans and a cute top. So I pulled out a couple sweaters I like and was thinking of black pants in lieu of blue jeans. I don't know. I really really don't know.

I  haven't yet put on an outfit that feels perfect. Maybe because I loathe the cold and none of these are sundresses. I don't know. Can I say that again? They all feel so dark and not cheerful and I don't knooooooow.

Option 1. Reddish sweater, black pleather pants, high wedges. Downside: they're actually jeggings and my sweater isn't that long. But I do kind of love them.

 Option 2. Same, except black jeans, and you can see the wedges. Jeans are comfy. Huge bonus is that I'm about 5'7" in these booties. Ha!

Option 3. Black jeans, black sweater, cowgirl boots. I could wear blue jeans instead of black. Can't decide how I feel about black jeans with the boots.

Option 4. Dress with cowgirl boots. Bonus: these boots kick ass. Also, I could wear a cool necklace. Downside, it may be cold cold cold. And my legs are kind of screamingly pale.

 

What I think it comes down to is: pants or dress; if pants, then pleather/jeans; all black or not; high wedges or cowgirl boots.

Or something completely different?