And why do you worry about clothes? See how the flowers of the field grow. They do not labor or spin.

Matthew 6:28

When my senior prom was coming up, my mom took me, my favorite cousin, and my best friend Mac to a mall in Pennsylvania (where there isn’t any sales tax on clothing).

I don’t remember how many dresses I tried on, but I know that I would come out of the dressing room and if anyone on my team shook their heads “no” to the dress, I put it back on its hanger.

I still remember the looks on their faces as they unanimously voted yes to a navy blue number.

In a couple of weeks, I’m going to a semi-formal event.

I don’t have an entourage to take me to the mall or help me pick the right thing out of my own closet. And I really, really miss them.

I’m pretty comfortable picking out my own clothes. I nailed down some seasonal uniforms and don’t think too much about what I’m wearing day-to-day. I figured out how to do some pretty killer eye makeup.

But Dressing Up is another thing. It’s a little out of my element. Matching fancy clothes with fancy shoes and possibly stockings? Ugh.

Beyond that, the nicer clothes I have are for summer events, because that tends to be when people get married (which is usually the only time I need to go semi-formal). I emptied my closet when I did Curated Closet, and got rid of the cold weather dress-up clothes I never wore.

Now, it feels like I have a bunch of odds and ends and I’m not really sure how to put them together to make an outfit that I can wear like a boss and feel confident that evening.

I’m feeling tugged toward online shopping, but I’m pretty sure whatever I bought wouldn’t be quite what I was looking for, or would be another version of something I already own. I tend to be guilty of both charges when I go shopping.

It’s hard to figure out what is You, and what is Idealized You. For instance, I like the idea of heels for a fancy night out, but I never wear them, so it would probably be a bad idea. I’m often drawn to bold colors and prints, but in practice, I almost always end up wearing dark neutrals. I like the idea of dresses and skirts, but I’m most comfortable in pants.

Could I wear some slick chinos and a nice blouse with flat dress shoes? I know Ellen could get away with it. But could I?

A few times since I RSVP’d to the night, I’ve opened up a browser and started looking around for ideas. Not long after, I’ll have 20 tabs open and be completely overwhelmed. It got me in my closet getting rid of things again just to clear my head and see if I could get a better handle on what’s in there.

I almost never dress up. Date nights, I can wear whatever I want. The Chaplain and I rarely go to events with a dress code. Since he has to wear dress shirts and khakis to work, and dress pants for church, he already has a closet full of stuff that fits pretty much any occasion. The Chaplain has more trouble when it’s a dress-down event. And I’m the opposite.

The sudden cold and wet weather makes taking on and off clothes just about the most unappealing thing I can think of. I know I should get a space heater up to my closet and just start trying things on. I’m a little afraid of what I’ll find. What if nothing works? What if I find something, but it’s missing an essential element that I can’t put my finger on?

I’m running out of time if I want to get something online. I could go to the store, but I can think of only a few things I hate more than shopping.

What do you do when you can’t figure out what to wear? Do you buy something new for special events, or do you have a go-to outfit in your closet ready and waiting? Do you have to do an online search before an event with a dress code to know what’s it’s ok to wear? (Yes? Good. Me, too.)

Have any advice for me? I’m starting to feel a little desperate.