All dressed up…and ready to get back in my stretchy pants

Tomorrow I get have to play dress-up.

I use the word “play” because I never dress up. In fact, the last time I wore a dress that you couldn’t wear flip-flops with and wasn’t purchased in the juniors section of Target was at this very same function a year ago.

My life isn’t glamorous, ya’ll.

I realize that might sound sad, but believe me, that’s just the way I like it. I live in cotton. Things that stretch. Beat up denim. Soft t-shirts. Long sweaters. Flannel pajamas. The three skirts I own could be paired with a Hanes tank top and jean jacket and look totally fine.

On the handful of occasions we do go out to a nice dinner I can usually get away with my good jeans (which tells you about the places we consider “nice”): the dark, skinny ones I’ve had since about 2010 that I always—always—pair with a solid black top (circa 2008) that I will lay to rest with full ceremonial fanfare when it meets its demise by entombing it in a shadow box that I will most likely hang over my fireplace and light candles under.

When we go to the theater—which we do five or six times a year because that’s our regular form of excitement—my go-to outfit is my black magic leggings (i.e., leggings with back pockets so they look like real pants instead of what they really are, which is fancy pjs) and, you guessed it, the hallowed black top.

Despite what it seems, the point here isn’t to make you pity me for 1) my lack of fashion originality or 2) my lack of a social life, it’s this: I’m comfortable being comfortable. Sure, I like to look fancy as much as the next girl, but what I loathe is the process. And the shoes. Don’t even get me started on the shoes.

Okay, fine. I’ll start.

The agony of searching—and paying—for a nice cocktail dress that you’ll wear once or twice is one thing, but having to endure the pain of feet being shoved into Barbie heels that were clearly made for Barbie-shaped feet is entirely another.

I hate heels, you guys. They’re pretty to look at, no question, but when your feet are used to being in either Converse, UGGs, flip-flops, or slippers for about 360 days a year, wearing them—much less walking in them—is excruciating and almost literally impossible.

But here’s the thing, if I’m dressing up in a real dress I’m damn well going to look the part. And wearing flats just doesn’t cut it like a sassy pair of heels, as everyone who reads Us Weekly, well…weekly, knows. So I compromise. I wear 3″ heels instead of 3 1/2″ heels, hobble around, and drink an extra glass (or two) of wine to alleviate the pain. You may call it coping (or alcoholism); I call it brilliance.

But the fashion stresses of an occasion that demands you step out of your stretchy pants for the night are just the tip of the iceberg. There are so many other things that have to be not only decided on, but executed.

For instance, how the hell do I do my hair when I’m wearing an actual, non-Target dress? Do I play it cool and act like I don’t give a damn I dress like this all the time and stick with the straight blow-out that will just look limp and lifeless after half an hour? Or do I spend 45 minutes painstakingly attempting loose, touseled waves that look so good on celebrities (courtesy of about 15 weaves and 3 hours of a stylist’s magic hand) but always make me look like Shirley Temple I tried too hard?

And what about makeup? Surely my daily, 5-minute routine won’t be enough. Do I try a smoky eye? If I want to look like a toddler applied my makeup, then sure.

I’ve heard that contouring is all the rage. Should I YouTube it and give it a whirl in hopes that I, too, will look like I have cheekbones chiseled out of Kardashian? Maybe not.

And then there’s lipstick. Since I usually stick with muted gloss, this seems like a good time to make a bold choice and wow ’em with red. IF I WANT TO LOOK LIKE A HARLOT.
Maybe a rich, dark plum? Since my dress is black (of course it is) I might run the risk of looking like Morticia Adams, but it seems like a comfortable fit given how I’ll be feeling anyway.

So, back to tomorrow night.
I found a great little black dress on sale—the kind it’s good to have in your closet since I’VE NEVER NEEDED A LITTLE BLACK DRESS FOR ANYTHING IN 46 YEARS—and got a pair of cute black pumps that actually feel comfortable for the 13 seconds I’ve had them on my feet so far. I imagine it will take at least 15 minutes before I’ve set up camp propped up against the bar. That’s called success no matter how you look at it.

As for my hair and makeup? I’m winging it, which I already know is a terrible idea and will most likely mean we’ll be horribly tardy to the event due to my many failed attempts to look like I just threw it all together at the last minute … which, ironically is what will ultimately happen.

All I know is this: for a few hours I might look like I gave a shit, but really? I’ll be counting the minutes until I’m back in my yoga pants and t-shirt with the happy knowledge that I won’t have to play dress-up again for another year, and the disappointing realization that I’d make a seriously crappy celebrity.



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