Skirting the issue

I hate the skirt I’m wearing today. I hate it every time I wear it.

It looks even worse in person. (And yes, I'm in a bathroom. DON'T JUDGE ME.)
It looks even worse in person. (And yes, I’m in a bathroom. DON’T JUDGE ME.)

It’s not that it’s just ill-fitting — this skirt is the definition of frumpy. I originally purchased it from a thrift store for BEANS. It was at least two sizes too big, but it was from Banana Republic, and I figured even with tailoring (it’s an A-line skirt — HOW HARD COULD THAT BE?) it would still be significantly cheaper than buying it retail.

Spoiler alert: Even tailoring has done nothing to alleviate the frump-factor of this skirt. It has these pockets, which I would normally love, but that stick out like a pair of book-size bat ears, giving my hips the appearance of being as wide as the day is long. (Note the weird pocket bulge on the right side of the above photo. I do not make this up.) Not exactly flattering.

In general, I have no problem getting rid of clothing that does not actively improve my life. You guys know this.

So why would I keep (and regularly wear) a skirt I feel like I’m in my own personal blood feud with? I like the challenge.

I’ve had an ironically torrid love affair with modest skirts in the last couple of years. Midi skirts? Those are my jam. And all of my pencil skirts run at least a couple of inches below my knees.

What I love about these skirts is that they are undeniably ladylike AND they force me to be more thoughtful about the rest of my outfit. I’m a firm believer that successful fashion is all about the give-and-take: shorter hemlines are ALWAYS paired with full-length sleeves and a lower neckline looks gauche with too much leg showing. Modest skirts require more effort to also look chic.

Which brings me back to the skirt in question. I’m telling you guys, I’ve tried my DANGDEST to get that thing to look fashionable. Sometimes, I think I’m close. A cute pair of nude heels and a fitted sweater will almost get us there. It ALMOST works because the skirt is so huge it makes my waist look tinier I GUESS? But the fact is, I’m constantly reaffirming in my head that I don’t look like a bag lady when I’m wearing it.

That is not the desirable effect of any fashion choice.

Am I the only person who has a piece of clothing with which I have this relationship? What would YOU do to make this skirt work? Or should I just accept that it IS ill-fitting and throw in the (frumpy, lumpy) towel?

You ARE our only hope.