OMGoodness, what is WRONG with me?

I love packing posts. I love packing pins. Yet when I try to pack... I always take twice as much as I need.

I'm heading to my mothers house for the holidays. My normal pattern for this trip is to hang out at home in pretty much exclusively Lululemon pants, a tee and a hoodie. This year, I want to try to dress a little more, at least a few times, given I now have comfortable casual clothes... oversized sweaters and cardis, and leggings, jeans I love, that sort of thing.

When I started to put things out, all of a sudden I have clothes for about a month, because I want to take all my favourite things. Even though I know I'll wear them once, or not at all.

Can you help me? I don't need help with specific items (unless of course you feel you know my wardrobe that well ) but with the numbers. This is what I'm going to be doing:
11 days, two of those with a five hour drive
Christmas dinner (which I'll dress up for)
Family photo (shades of blue and black) (may or may not coincide with the Christmas dinner, so I'm allowed a second outfit for this)
Shopping/errands 2-3 times
Going to an afternoon play
Visiting people 2-3 times
And a LOT of hanging out drinking tea

So, a plea to those of you who travel a lot. How many bottoms is reasonable? How many tees and toppers? Yes, I can do laundry. Maybe if I have some numbers, I can whittle this all down into something reasonable.

Oh, and it doesn't really matter... I'm driving, and have lots of space. I just find it frustrating how difficult I find this. I think my casual clothes mix and match well! So if I can't get my act together, then taking it all it will be.

So, if you want to have some fun, love some help!

Also would love to open up the conversation to anyone who experiences the same thing, and how you've dealt with it.

Pieces I find comfortable, and am considering, I'll put in finds, where I can. See, too much already!