Typically my deliberations over what to wear go something like this:

“Hmmm, bra or tank top with shelf bar?”

“T-shirt or sweater, lift or unzip?” It’s a nursing thing.

“Jeans or something that isn’t jeans?”

“Pony tail or Red Sox cap?”

“Ankle socks or wool socks?”

This routine lulls me into a false sense of being low maintenance. Then events like the big one I have coming up next month bring to light the reality that I am actually a girl who, dare I say, likes getting dolled up…maybe even tarted up. If only that were as easy to do as it is to imagine.

We are less than 3 weeks away from the big event and I have nothing to wear. Literally. Because even I know that I can’t make jeans or cords work at this event no matter how many sequins I incorporate or how thickly I lay on the mascara. Seems that in some fit of longing for organization I threw out all the slinky little this and thats I had purchased over the years. Surely I could have cobbled together an outfit with a chiffon skirt and spangled halter, no?

No.

I am 33. A mother of two. I cannot work Wet Seal and TJ Maxx clearance buys into something appropriate for an almost black tie event. As I find my age group in online surveys moving closer to the middle and further from the perky 18- younger than I am age, I realize that certain kinds of tank tops are not appropriate outside of the house (unless of course I am wearing a hoodie or am out on a walk with a Baby Bjorn covering parts
(So sue me, I can’t quite embrace all the rule of fashion appropriateness when it’s really hot. But I swear that when the time comes I will have the good sense of Diane Keaton to cover stuff up and look ravishing…please can I look that good when I am 60? Vain? You bet. Are you telling me you don’t want to look like Diane Keaton? Helen Mirren?)

So I am in the market for a dress. Or an outfit. Though, as I learned in my travels online tonight, not
the flippy, fun evening top and slacks look.

“Naw. I’ve seen you do that. A lot. Yeah, you’ve done that look many times.” Sean told me dismissively.

Ugh. Great. I guess just cause it ain’t broke doesn’t mean you shouldn’t fix it.

Let me share some ideas. This first one, I would never in a million years have the balls to wear. And besides, if I had balls, it would just be really weird if I wore it.

It’s cute though, right? Maybe 8 years ago. Probably not. Anyone who has the nerve to wear this, I envy you. Buy it, wear it, send me a picture you ballsy gal you!

Ok, the next one, same brand as the previous, but with an actual chance of me wearing it. However after some reflection I think that the theme of the event, That’s Amore, this dress would make me look like a server. Or some sort of evening attired spanish soldier.

Sean said black dresses were super predictable and didn’t I want to look different. Then he saw the pathetic so-help-me-I-am-losing-all-hope-and-may-have-a-breakdown-any-minute look and said, “Oooh, that one’s nice.”

This is what I call the cute, but no way in hell I’ll wear it cause it’s a tired look top.

So where does this leave me?

I honestly don’t think he’d agree to have me on his arm if I wore a kimono.

This little number is $1500 on Bluefly. Call me crazy but it looks for all the world to be an evening version of the dresses Loni Anderson wore on WKRP.

With this one I’d have something to do with my hands when I got nervous. I’d just braid the night away.
“What’s that? You’re nervous too? Here, you braid the back.”

Of course I could always go the “I know it’s a boring design, but the potential for nip slips make it tough to look away” type of dress

Anyone wanna conga?

I am no longer having fun despite the festiveness of the last dress. What the hell am I going to wear?