My husband and I are having a date tonight, and I have no idea what to wear (I have about six hours to decide, which should be plenty of time, but still). I am completely stumped, you all.

Here’s the scoop: We’re going to a charity auction for a group my husband is involved with, so this is essentially a work function for him. The event is dinner, a silent auction, a live auction, and a performance by Toby Keith. The whole shindig is taking place at a casino outside Oklahoma City.

Oh, and? There’s a pretty good possibility that we’ll get to meet Toby Keith.

Seriously, do you see why this is throwing me?

I have a hard time getting dressed for those in-between events, the ones that require something nicer than what I wear on a normal Tuesday but don’t quite warrant a cocktail dress. Date night is always tricky for me, partly because my husband and I do such oddball things for our dates. And work-related functions feel extra complicated because I don’t want to make my husband look bad.

(You can laugh at that, but I’m serious.)

At this point in the day, I’m building from the bottom up; I have a really cute pair of pink patent peep toe pumps that I haven’t had occasion to wear yet, and they seem perfect for this evening. Now I just need to find something to pair them with — cropped pants? skinny jeans? a pencil skirt? And then I need something on the top.

And of course there’s always my little black dress — if I wear it with silver sandals, it’s a little less dressed up and a little more simple chic.

In the end, I’ll probably wait until the last minute and then just pull on whatever seems like it will work. But I’m curious — what do you wear for date night? Does it depend on where you’re going? Or on what you’ve been wearing all day? Dish — and next week we’ll do a roundup of best date night outfits!

Share your date night favorites in The Working Closet Flickr pool — and you might see your photo right here at The Working Closet Blog!