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What Was I Thinking?! Coming Clean About My Fashion Eff-Ups

Even though we’re old enough to know better, sometimes we succumb to the siren call of fashion purchases that wind up looking ludicrous. Janet Siroto airs her worst mistakes

Part of our series of articles about what we wear and how clothes make us feel.

One of the more convenient things about reaching midlife is knowing your sense of style. Remember what it felt like, years ago, to be sorting things out—the time invested in dressing rooms under god-awful fluorescent lights and thoughtfully thumbing through catalogs and Glamour magazine, folding down the corners of pages?

But now, most of us have arrived. We know to keep walking when a friend points out a peasant top in an Anthropologie window and squeals, “Omigod, that’s so you!” Our significant others (if we are lucky to have one) know just the shade of blue in a silk scarf will make us drool.

So please explain to me why, as a legit grown-up woman, I keep making such ghastly mistakes, plunking down good money for garments that don’t suit me? At all. Granted, the term mistakes is harsh and loaded. Maybe I should say missteps or failed experiments. But it’s one thing to be 23 and have an unfortunate foray into a football-shouldered power suit or Betsey Johnson rose-strewn spandex. It’s another to be an Osteo Bi-Flex-chomping adult who commits crimes against fashion.

Venturing Beyond Uniform Mode

Most days, I’ve got my fashion thing figured out. My style has pretty much glided into uniform mode, with a dozen pairs of black pants (I can tell the difference between the lengths, pockets, and creases, though I’d defy anyone else to), a healthy supply of Liberty of London print tops, and a load of cardigans. But I love fashion as much as the next person. Heck, I even worked at Vogue for a year or two, where I sadly discovered I wasn’t a genuine fashion person, as I couldn’t throw a legit fit over bias-cut seams or pronounce turquoise as tur-KWOZ with a straight face as my colleagues did.

My clothing lust and craving for something new leads me to flit, magpie-like, over to what’s shiny and new. That’s why my “What Was I Thinking?!” fashion moments keep on coming as my years advance. The situation usually begins as an effort to update or emulate someone else’s style (curse you, Instagram, for your role in this!) and ends up with a garment that is all but saying “Nyeah nyeah” as it hangs in my closet, unworn, till I offer it up to friends or charity.

These are some of my recent incidents:  

The Siren Call of Skinny Jeans

This look has been going strong for a few years now, and all the young ‘uns seem to go about their day unfettered in these pipe cleaner-lean pants. While I knew better than to get the ones that have gaping, pre-torn holes in them, I did find myself mesmerized by the J.Crew sale selection not too long ago, and gingerly picked my way through the categories—I recall names like Matchstick and Toothpick—till I found a becoming pair and on final sale.

Bingo! Good and cheap.

Remember the Seinfeld episode where Kramer wears those jeans that don’t allow him to sit?

What I discovered upon wedging myself into them and heading off to meet a friend is that the sliver-slim legs of the pants hold your range of motion hostage. Remember the Seinfeld episode where Kramer wears those jeans that don’t allow him to sit? Check. Every time I bent my legs, I expected to hear a dramatic ripping sound, and I became acutely aware of the pulse behind my knees. So the pants are accumulating dust in my closet. Fortunately, the latest denim style I’m seeing is a modified Mom jean—a bit baggy and high-waisted as all get-out. That I can do.

The “Notice Me” Baseball Jacket

Image: Julian Florez/Unsplash

There’s a Zara next to my local subway stop, and in the window a couple of years ago were reversible satin baseball jackets. I mean, think about it—reversible! Solid satin on one side, and, presto-chango, turn it inside-out and you’ve got a whole other look with a tiger embroidered on the back!

Did a group of teenage girls just fashion-shame me out of wearing my new purchase? You betcha.

Somehow, my 16-year-old self re-emerged as I passed the store window and demanded that I possess this item. I went in to buy one, telling myself I could wear it on weekends with jeans (ones that allow my knees to bend, please) or to the office with black pants (got plenty of those), but my size was sold out. You betcha. And no wonder, it was so popular it was deemed a “fashion blogger favorite” all over the store. I had to stalk it on eBay and Poshmark and finally nabbed one.

On its maiden outing, I went to Starbucks and was standing in line with a gaggle of teenage girls behind me. As I stepped up to order, I turned and saw them looking at me, then clearly focusing on the tiger emblazoned on the back of my jacket, and me again. They were totally silent, and not in the way that they were dazzled by my fashion sense. I paid for my coffee and left…to a chorus of giggles. Did a group of teenage girls just fashion-shame me out of wearing my new purchase? You betcha. I’m not saying I’m too old to wear it, but my ego needs to recover.

The Allure of the Lady Dress

Every now and then, I reflect upon the fact that I never learned to dress like a grown-up—or the way grown-ups dressed when I was a kid: Stockings, heels, a flowy floral dress. Think back to parents’ visiting day when you were in 5th grade … like that. One day, I decided it was time to start working that look and wear something full-tilt feminine.

What felt fresh and summery in the store looked like the bad, sad aftermath of a sugar-sodden kiddie birthday party when I got home.

With a spring wedding coming up, I had a good excuse to buy a flowered lady dress, and with a hazy flower field in my mind’s eye, I found a designer number at 70 percent off (still expensive in my book) and wow, did I ever go frou-frou. Chiffon with spattered with a big bouquet print, slightly tight and short, with a swoopy neckline and satin belt. How many things can you find wrong with this picture? What felt fresh and summery in the store looked like the bad, sad aftermath of a sugar-sodden kiddie birthday party when I got home and tried it on. I wore a plain LBD to the wedding and that was that.

Running in Heels

Back in 1987, I had a pair of heels I could really move in. Since then, I’ve never found my groove, despite multiple attempts. Honestly, like Charlie Brown racing towards that football Lucy promises to hold steady, I keep lunging in the direction of so-called “comfy heels.”

Whoever created the oxymoron ‘comfy heels’ is a marketing genius.

Whoever created this oxymoron is a marketing genius. I fell for this line a few years ago when there was a collection of way-pricey shoes supposedly designed by a podiatrist. I chose a cute, retro pair…sort of flapper girl with little buttoned straps. I was so thrilled with them till I came home from wearing them out in desperate need of a tube of bacitracin and half a dozen Band-Aids. I’m back in my super-boring black flats and not looking back.

All of these items remain in my closet, reminding me that fashion faux-pas are part of life, no matter how old and wise we may be. I’m happy to view them as similar to scars, showing that we’ve lived and tried new things … had adventures and taken some knocks. It’s all good. But,  hey, if any of these garments sound appealing, and you’re a size 6…hit me up.

Share your “What Was I Thinking?” fashion moments with the Tribe–the funny, the feeble, the flat-out awful. Let’s laugh together.


The wonderful Janet Siroto has held the Editor-in-Chief position at Time Inc.’s Family Life magazine, as well as senior editorial positions at Cosmopolitan, Redbook and Good Housekeeping. Her writing work has appeared in New York, The New York Times, Vogue and many others.

More in Our Fashion Series

Should You Wear Vintage Clothing When You’re…Uh…of a Certain Vintage Yourself?

Sustainable Fashion: This Fall’s Bounty Is Good for the Earth

Further Reading

Shopping for the Real You: 10 Essential Steps to a Better Wardrobe for Every Woman: Fashionistas, Fashion-phobes, and the Over 50

The Curated Closet: A Simple System for Discovering Your Personal Style and Building Your Dream Wardrobe 

Bad Fashion: 80 Fashion Disasters You Swore You Never Wore

By Janet Siroto


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