I'm packing for a road trip this weekend, if by "packing" you understand me to mean "intermittently standing in my closet wondering what precisely one wears for a day of wine and cheese tasting."

Flats, I guess. I mean, because of all the wine tasting.

(Yes, I know you spit it out after you taste. But still. Flats.)

I have made a big effort to carefully curate my closet, to buy only pieces that I will really wear and that will work together. And yet, any time I am packing to go anywhere, I discover two things about my carefully-edited wardrobe.

1. It doesn't say what I want it to say about me.

2. Nothing goes with those great black pants.

That second thing is easily solved (note to self: shop for something to go with the great black pants! And take the pants along when you're shopping, because that way you will be certain that the outfit works). The first, I fear, is the bigger dilemma.

I love my clothes; there's not a single thing hanging in my closet that I don't enjoy wearing. On a normal day, I can whisk in, pull together an outfit, and whisk out, ready to get on with the business of doing whatever is on my calendar. But traveling, especially to events with specific functions (wine tasting!), always throws me.

But it's not about my clothes; it's about something else. It's about wanting to look like a better, smarter, more interesting version of me. Like someone who goes to wine tastings all the time.

(In my everyday life, I'm more someone who asks that nice guy at the liquor store if he can recommend a white that retails for under $15, please. Fortunately, he's good at that.)

A trip like this one always ends with me putting together crazy outfits, things I would never wear together in my normal life, either because the proportions are all wrong once I put them on or because they're just too dramatically different from what I usually wear. And at some point in this crazy mix-and-match routine, I start to wonder why this is so hard, why I can get dressed every morning so easily but now I cannot find three days worth of clothes to put in my suitcase.

Argh.

The bottom line for me is this: I'm not good with new looks; I like my routine, and my comfortable closet of Outfits that Work. But a trip always seems like an opportunity to be someone different, and the easiest way to do that is to wear something different! And that leaves me either packing a bunch of brand-new pieces (never a good idea, really) or furiously mixing and matching old standbys in the hope of creating a Better Me.

One that fits in a small rolling suitcase, of course.

In the end, I'll be taking my favorite pieces this weekend and wearing them the same way I always do. But what about you -- is a trip an opportunity to try out a New You, or do you just pack your regular uniform and go as your everyday self?