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

Power suits and MC Hammer “You Can’t Touch This” drop-crotch pants clog the racks at vintage clothing stores. Can those of us who wore them when they were first hot sport them again? Stephanie Dolgoff investigates.

Vintage Clothing Dilemma at Midlife: Am I Too Old to Wear This? | NextTribeThe first in a series of articles about what we wear and how clothes make us feel.

I’m one of those women who always played out the vestiges of our collective hunter-gatherer instinct by continually shopping for clothes, often at vintage stores. Having only one body to cover and two feet to be shod, I don’t technically need anything—and haven’t since 1996. But that doesn’t stop me from being sucked into the carefully curated boutiques I pass as I walk around the city where I live, falling into a trance as I flip through racks.

Any young adults in your life would, like, literally die to wear your ‘Frankie Says Relax’ tee and your high-waist Sasson baggies.

There is a self-soothing aspect to stroking the sparkly beadwork on a 1950’s cardigan, or holding up a flouncy 1980’s girls-just-wanna-have-fun bodice dress in front of a mirror, if only to remind myself that I’m not a girl so, yeah, no. It’s like when I flirt with the 20-something pharmacist at CVS, which my teenagers have informed me I do by rote. Thirty seconds in, I remember that the (my-age) guy I have at home is more to my taste. I walk away feeling as if I’ve missed out on nothing. Been there, done that, 25 years ago.

My Vintage Clothing Rule

But just like the knee-jerk pleasing of others and climbing a StairMaster to get a better butt, vintage shopping has become a LOT less rewarding as the birthdays have passed. That’s because around 10 years ago, a personal rule took shape in the region of my brain responsible for fashion decisions: That if I wore an era’s iconic clothing unironically during that era, I should not wear it the second or third time around. This is my VFG, or Vintage Fashion Guideline, and it works for me.

Whenever I consider patchwork bell bottoms and a calfskin suede fringe vest I whisper ‘VFG,’ to myself.

The VFG took shape when I was in my 40s and the ‘80s were briefly back. Trying on a blazer with shoulder pads or pegged trousers with ankle booties made me feel as though I was off to a costume party or that I hadn’t purged my wardrobe at all since my first job interview out of college. I passed these garments by.

Now, whenever I consider patchwork bell bottoms and a calfskin suede fringe vest with die-cut peace signs on the breast (I remember feeling happy when I wore an outfit like that when I was 10), I whisper “VFG,” to myself, breathe, and come back to the moment.

If you have small children around, my sense is that items like these, which you enjoyed when they were new, belong in the dress-up bin. Any teenagers or young adults in your life would, like, literally die to wear your “Frankie Says Relax” tee and your high-waist Sasson baggies—I know, I know, you paid $35 for them, a fortune in 1983 dollars! I’ve donated many such items to Goodwill, where a vintage scout probably plucked them from obscurity and resold them at the aforementioned curated boutiques for way too much money. That’s fine—as long as they’re not in my closet, reminding me of how many decades have passed since both they and I were wrinkle-free!

The Retro Styles That Look Right

Vintage Clothing Dilemma at Midlife: Am I Too Old to Wear This? | NextTribe

Image: Becca McHaffie/Unsplash

I’m not saying it’s easy. For me, born in 1967, the VFG means that if I might have rocked that 1980’s Cyndi Lauper frock at my prom—and I might have—then it’s a hard pass. I actually wore a vintage 1950’s dress to my prom in 1985, when the ‘50s were kind of retro-in, but let’s not complicate things. And if I could have worn a pair of MC Hammer “You Can’t Touch This” droopy crotch harem pants in the ‘90s—I didn’t, but I did overdo the whole sunflower motif and wore chokers and Docs—then there’s no way I’m buying them now.

I feel my window of appropriate vintage clothing is closing year by year.

That leaves me with a sad selection from the 1960s and earlier, when women tended to be smaller than I and also willing to put up with suffocating girdles and bullet bras. In recent years, I have picked up an early 1960’s Hawaiian flower-print resort wear maxi dress that I like to think makes me look like I spent the day sunning myself and then mixed a highball for my breadwinning ad-exec hubby when he joined me poolside at our getaway in Palm Springs. I also just bought a ¾-sleeve raincoat from a little later that screams striving career gal who, although relegated to the steno pool, believes she will soon overcome the wall-to-wall sexism of her workplace and be a major player by dint of her obvious talent.

Still, I feel my window of appropriate vintage clothing is closing year by year. Of course, there are always the classics that predictably cycle back several times a decade: Navy pea coats, MC jackets, and cowboy boots come to mind. But I have already owned all of those at least once, so the thrill of the purchase isn’t what it was.

Luckily, my kids inherited the vintage gene, and it buoys me to take them shopping. They take such ironic delight in the stuff we wore way back when. On those trips, I limit myself to only one sniffly reminiscence of hearing Billy Joel play “Allentown” live in 1982 when they ask me to buy them a T-shirt from that very tour.

While they’re in the fitting room, I peruse the accessories. That’s my one exception to the VFG: When it comes to shoes, bags, belts and jewelry, why not? I can pull off a chainmail disco-era crossbody purse with my otherwise modern-era outfit! And if I decide I can’t, then it can go to Goodwill and thrill some cute 22-year-old who will wear it out with her friends, meet someone so totally OMG or whatever, and end the night believing she and her new love invented sex. It’s the circle of life. And I get a tax deduction.


Stephanie Dolgoff has contributed to a a variety of titles as an editor and writer, including  SELF, Glamour, “O” The Oprah Magazine, Redbook, and many others. Her articles have also appeared in the New York Times and the New York Post.  Her book, My Formerly Hot Life: Dispatches From Just The Other Side of Young, was a New York Times national bestseller.

More in Our Fashion Series

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

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

Further Reading

The Little Guide to Vintage Shopping: Insider Tips, Helpful Hints, Hip Shops

Vintage Notions: An Inspirational Guide to Needlework, Cooking, Sewing, Fashion and Fun

Vintage Shoes: Collecting and Wearing Twentieth-Century Designer Footwear 

By Stephanie Dolgoff


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