Guest Guru: Alisa Singer -Dear Grumpy Aging Boomer

Article and Illustration by Alisa Singer.

Dear Grumpy Aging Boomer,
I’ve always considered myself a fashionable lady, but now it seems that nobody cares about the average middle-aged woman. I’m feeling more and more irrelevant to the fashion scene. Is there anything to be done?
Hopelessly Out of Style

Dear Hopelessly Out of Style,
As an aging female baby boomer myself, I have to agree the situation is looking pretty grim. Overall, 1 out of every 4 adults in the country is obese, and among older boomers that number goes up, in fact way up; a significantly larger percentage of us are just plain overweight. Ok, so we’re generally a bit plump and, despite our best efforts, rather old. (The first boomers turn 64 this year.) And then, as we cling precariously to the edge of the fashion runway, Michelle Obama becomes our new first lady and we find ourselves spiraling into the abyss of fashion obsolescence.

Well, it’s certainly not news that older women have been increasingly marginalized and excluded from any meaningful place in the fashion world. Our star’s been waning for a while, but ever since Lady Bird Johnson, whatever else was happening on the pages of Vogue and Bazaar, we generally could rely on our first ladies.

Admittedly, the bar was set pretty low by the age-appropriate dressing matrons that headed the first household over the past four decades. Not to be mean, but think about it – Lady Bird, Pat Nixon, Betty Ford, Barbara Bush … The former screen actress Nancy Reagan certainly was a fashionista of sorts but, after all, she was turning the reassuring age of 60 when she assumed her place in the mansion. Following her fashion lead wasn’t all that daunting – wear red and look imperious. Even Laura Bush’s pleasing appearance had an everywoman kind of librarian appeal. But Michelle, well – what can I say –we would at least have had a shot with Hillary.

Of course, there is so much more to Michelle Obama than her striking looks. But regrettable as it may be, an inevitable facet of the role of FLOTUS is her influence on fashions of the day. Which is, of course, all well and good, but not so much for us aging baby boomers. Maybe sometime in 2018 a woman that looks more like us will again toddle onto the stage, but by then we’ll be past caring, having long since graduated from our mom jeans to elastic waist pants and, as we all know, there’s no way back from there.

Oh, of course, nobody will feel very sorry for us. We’ve had our moments, in fact decades of them, but still it’s painful to realize our time has come and gone. Just summon up the image of the average 50/60-something woman in mid-thigh shorts, a pencil skirt or a sleeveless lemon yellow fitted sheath and I think you’ll get the message pretty clearly – “No we can’t.”

Here’s my advice: Start one of those annoying email petitions and get thousands of middle-aged women to beg Michelle to bring back the pillbox hat– we could work with that – or better yet, the flowing kaftan.
If all else fails, we’ll just have to be satisfied relishing the hopeless discomfort of all those paunchy middle-aged men, aka our husbands. After all, consider what they’ve got to deal with – that unforgettable, awe inspiring image – Barack Obama in swimming trunks.
Gabby with text

Alisa Singer’s humorous essays have appeared in a variety of print and online newspapers and magazines across the country and in Canada. She is the author of the books I Still Wanna Be A…, an illustrated collection of whimsical poetic fantasies in which she “morphs” herself into her childhood heroes, and My Baby Boomer Memory Album, an album to memorialize the first grand child, social security check, chin hair and other milestones of the second half of the boomer’s life. You can learn more about her work by visiting her website: or contacting her at