Should it Stay Monday: Christmas outfit traditions

I keep forgetting to link my Style All Over posts here! Last Thursday I wrote about what I normally wear for family Christmas celebrations. We usually have five and I wear a nice sweater (or maybe shirt) and jeans to four of them. Each outfit has to be different because we take LOTS of pictures. (I suppose they don’t have to be different, but I like it that way.)

The problem is that four sweaters per year is kind of a lot. I do repeat sweaters from year to year, obviously, but I try to at least dress them a little differently – new jewelry, maybe a skirt instead of jeans. It’s not that I mind wearing the same thing year after year, or even twice the same year; it’s that I like variety. Aside from the Blathering the last couple years, this is my one chance to really “plan” outfits with makeup and jewelry and everything. It’s fun for me.

The main reason I go with sweaters is most of my family dresses very casually for these things. At least half are also in sweaters/jeans and the other half are often dressed down further. I don’t mind this at all, but I don’t want to be the one person in a dress, you know?

Again, though, five outfits, four of them quite similar, is a lot and usually only a couple of them end up being an ensemble I really love. At least one, often two, I don’t feel good about at all. Take this sweater: it’s static-clingy, yet lumpy, and, to top it off, uncomfortable. But it’s a red sweater and therefore, in my mind, Christmassy. I think I wore it for two, maybe three, Christmases.

Christmas 2009 with bonus baby Margaret!
Also, 2009 Jessica needed to learn to accessorize.

I don’t really expect anyone would vote for me to keep it after I went ahead and said I just don’t like it and it doesn’t wear well, so I’ve already donated the sweater. I do want your opinion on the overall issue, though. If I come up with two or three great outfits, should I just wear them over and over? Or stick with my something-different-for-every-celebration plan?

Like I said, I love planning five different options, even if one doesn’t work out – as I sit there all uncomfortable, or at least thinking I didn’t knock it out of the park with that one, I’m still loving the fact it’s different and that I made an effort. I get a sort of perverse pleasure out of it, actually, that makes up for the uncomfortable aspect. It’s not quite as good, though, as the feeling of being in something I really love.

But the one outfit that’s set in stone already this year is pretty dressy (meaning I might be out of place) and pretty distinctive (meaning we’ll look back at the pictures of Christmas 2012 – which I actually do often – and think, wow, Jessica really loved that dress, huh?), which makes me lean against repeating it.

Basically, I’m going in circles over here. Does your family take a lot of pictures? Does that make it less likely for you to wear an outfit more than once? What do you think I should do? Please comment!

What should I wear for Christmas this year?

P.S. I should say I'm talking about the picture-heavy family celebrations only. I do wear some of the same outfits I wear on those days to other Christmas parties. The set-in-stone outfit I mentioned above I wore to a Christmas party last night!