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Infamous last words, no? Personally, I must utter them 42 times a week, much to my husband’s bewilderment. You see, he’s misled by the sheer number of clothes he sees me flipping through on my screen, or futzing with in a box, or rearranging in my closet in a futile attempt to simply “get dressed.” Because, you see, my body is of a certain age. And outfitting a body of a certain age is no simple task.

In a way, I have always struggled to get dressed. I remember feeling freedom around my first fashion choices, for sure. I would spend hours at Quintessence, dazzled by row upon row of neon rubber and fishnet, or make a quick dash between classes to Benetton for a new rugby. But even then, once at home and in front of my mirror, I’d be struck with indecision. It’s hard to forget that anticipatory excitement, turned eventually into angst, of deciding what to wear to the first day of school. But it was fleeting, once a year at-most. And now, let’s just say, it’s more than that. In fact, every woman I know has experienced that slow creep from the bright prospect of getting dressed to the inevitability of it stressing her the f-ck out, probably in the past week alone.

Throw in that you need day outfits, night outfits, day-to-night outfits, party wear, office wear, service wear, winter wear, summer wear, and in-between-season wear, “resort”, something in case it’s a little chilly at night, something to wow your uptown friends but not repulse your downtown friends, color, lots of color, but then monochromes, with the right shoes, spanx, jewelry, bra, bag, etc. --

Oh, the Thinks I Could Think if I didn’t have to worry about what I was going to wear…

Which brings me to the exponential conundrum of dressing on the wrong side of forty. Shouldn’t this be easier by now?! I mean, women are used to their bodies changing (we did puberty, adolescence, pregnancy, thank you very much) – but we are still stymied when the volatility becomes so systemic that even looking at a packet of soy sauce causes us to puff up in a post-sushi Sumo bloat. I have yet to meet a woman over 40 who hasn’t had the experience of putting on her favorite pair of jeans, the ones that always fit like a glove, and one day, saying WTF?! So, alas, no, easier it is not.

With age comes wisdom, and yet, never have I been at such a loss for what to wear. Most of us figure it out eventually but yes, ladies, the struggle is real. To dress a woman of a certain age, one must be creative. In the blink of an eye, your old clothes, you know the ones – the bold, belted shorts, that cute, frilly number that you thought you rocked a mere few years back - suddenly look like they belong exclusively on the legs of a 13-year-old girl. How about long and flowy? Surely that must work, no? Except, like, I am giving off dowager-vibes…

A 40-plus woman wants to look young but not trendy, mature but not matronly. They don’t want to dress like their daughters, or their mothers – but they don’t have much of a choice. I mean, mom jeans are now sold in kids’ sizes at Zara. Thanks for that! Suddenly, mom jeans are being rocked by 10-year-olds everywhere, which makes them Grandmom jeans on the rest of us, I guess. And we have no choice; we’re not quite ready for a nice pair of slacks.

Lastly, can we have a brief chat about cut out dresses? What fresh hell is this?! As if it wasn’t hard enough to find a good dress, they are now cross-pollinating with bikinis. Wasn’t the cold shoulder just supposed to be an errant bad idea that died? No one asked for the holes to to be moved. The brilliant marketing team at Spanx needs to figure out how to put the kibosh on this, and ASAP.

For now, I will keep filling up my online carts with items that look interesting, and then applaud myself for saving good money when I remove all but two of them. I’ll play dress up, or dress down, all while searching for my Goldilocks-ian mark in middle.

Yes, sometimes I wistfully recall the simplicity of my Benetton days, but I also embrace the challenge of searching for a new pair of jeans amidst the 2456 styles they released this season, all modeled on 18-year-olds. In the meantime, I’ll complain that I have nothing to wear… Capiche?


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