"Timeless classics"

So I'm of the opinion that the "timeless classic" - that clothing item or accessory that will never look dated - is a myth. A myth embraced by brands and consumers alike, because everyone wants to work under the impression that purchases will be worn for years. Stores want customers to think they're getting a good deal and being sensible, and that this justifies spending an extra thousand dollars on a certain brand of raincoat or whatever, while shoppers pride themselves on good taste and eschewing frivolity.

How timeless is timeless? Are we to believe that Louis XIV's Levis and Converse would totally work today? It would make sense that a "classic" would be a look meant to stay in style for the duration of a normal human lifespan, or the years of it spent at more or less the same size. But then there are those watch ads, with the father who'll pass down the watch to his insufferable looking son, styled to resemble Brighton from "The Nanny." For every item costing over, oh, $1,000, there needs to be at least the notion that it will stay in one's Fine Family (as opposed to the Fine family) for years.

There are several reasons I doubt "timeless" is a real phenomenon, beyond the marketing. For one, even if you restrict your sample population to one subculture, how that subculture dressed in 1979, 1988, and today will not offer much in the way of direct overlap. Take a subculture known for timelessness: preppies. The general idea and color scheme remains the same, but the specific brands and styles come and go. (Remember Hervé Chapelier? Once ubiquitous, now at the bottom of every closet on the Upper East Side.)

Next, there's the fact that brands and styles known as "classics" aren't so much timeless as prone to cycle in and out periodically. Keds, Doc Martens, motorcycle jackets, these will probably never leave us altogether, but they go through decades of being 'that thing I wore way back when' before returning to social acceptability.

Finally, there are the many, many, many subtle changes - i.e. "fashion" - that make clothing either look "then" or "now," but that are not always predicable at the time. The obvious example is pant-leg flare vs. taper - a bit of fabric makes the difference between looking like you've made an effort and looking like you last bought pants in high school. (Which, given that it implies a constant dress-size since high school, might be something some would want to cultivate?) There is not a single pair of jeans in this universe that will always look current. The cut of skirts presents the same issues - pleats, waist height, and overall shape, not even bringing in the issue of hemline. I mean, I can look at t-shirts I bought a few years ago and detect their few-years-ago-ness, even if they're still in decent shape. It doesn't stop me wearing those t-shirts, but the point isn't whether one can continue to wear clothing for years (one can, and the one that's typing this sure does), but whether one's closet, if properly stocked, can make one avoid looking dated.

A commenter, however, claims that "timeless" exists. I'm willing to accept the possibility, but only if specific timeless items, or better yet full outfits, are identified. So, readers, if you have any ideas, comment away.