Before we discuss what’s gone wrong with boomer fashion—and provide some suggested remedies—let’s first do an important disclaimer. Some boomers dress beautifully, look youthful without looking young, have achieved a sense of ageless beauty and spend plenty of money on beauty and fashion, but do so wisely.

There are enough of these best-of-class boomers to constitute a critical mass, which is why many who observe and comment upon the incredible defiance of the stereotypes of aging amongst this generation, include style and fashion on the list of attributes. The issue is that the critical mass, while real and genuine, is only in upscale urban centers, like New York, Chicago and San Francisco—places where magazine editors tend to hang out; high-end fashion designers live and work, and the smattering of style-conscious 50 and 60+ female celebrities who are still working (does not include Goldie Hawn or Susan Sarandon, especially in some of their recent roles, i.e. Goldie as an aging groupie and Susan as a Disney-esque witch) and look fabulous.

Then there’s the mass market.

Sherrie Mathieson, author of “Forever Cool: How to Achieve Ageless, Youthful and Modern Personal Style for Women and Men”, began noticing the “reality” of boomers and fashion when following her career as a film/TV costume designer and stylist, she moved from NYC to Tucson and begin offering fashion adviser services to a private clientele. The woman (and men) who showed up at front door were amongst the most motivated of the generation, determined to look good. But with few ads and icons, they were seriously confused. And they are the best of the generation.

What went wrong? From the boomer perspective, the transition from the 50’s to the 60’s and 70’s constituted a welcome and lauded liberation from the rule-laden universe Madmen is describing so well on late-night TV to the whole universe of choices.In their youth, boomers burst through the ladies-who-lunch aesthetic of white gloves and pointy bras, bringing the hippie values to how they chose to dress and live. They borrowed from every ethnicity, geography and fantasy they could conjure up, as long as it was comfortable to wear and ergonomically-based. The original recyclers, they opened free stores and touted the beat-up used clothes ethos, from mis-shaped hats to scruffed up shoes—and on 20-year-old bodies, the look worked.

When the decades began rolling into the late 70’s and 80’s, and it was time for late twenty and thirty-ish boomers to “grow up and go to work”, there were no transitional role models to show the way. The “Dress for Success” books, that touted the most boring dark black and blue man-suits as the only solution, were the only guidance on the horizon. And the boomers bought into it. There was no transitional fashion possibilities that grew up hippie style into grown-up style. It was all on or all off. And the boomer generation’s parents weren’t any help, either. In the aftermath of the studio system, even icons like Elizabeth Taylor, who were once dressed both on and off-screen by their studios, were now left to their own devices when not on the set. Meanwhile, the fashion sense outside of the corporate world of work went to glam and polyester.

In the next blog: Where fashion designers and retailers went wrong.

Carol Orsborn