When it comes to making wearable tech “cool” for the masses, Anna Wintour may end up being more influential than any entrepreneur in Silicon Valley. In Vogue’s much-talked-about September issue (a paean to fashion so influential that it was even made into a documentary in 2009), sleek, sophisticated models wearing Google Glass appear in a 12-page fashion spread that includes the futuristic background of a UFO-inspired home. So is this the season that wearable tech is not just in Vogue — but also in vogue?

The Google guys certainly hope so. They hope that the Vogue fashion spread does for Google Glass what the company’s partnership with Diane Von Furstenberg did in 2012 – make Google Glass not just a technological gadget, but also a must-have fashion accessory talked about by fashionistas as much as futurists. Aligning Google Glass with the modelista crowd will not only justify the product’s high initial price tag – it may also help Google break the near-monopoly on cool design that Apple has had on the technology sector for years.

Which may explain why Apple appears to be rushing into the wearable tech sector at the exact moment when Google Glass is about to hit the consumer market. Apple just hired away Jay Blahnik, the “guru” who led Nike’s FuelBand initiative, and recently poached away Paul Deneve, a top Yves Saint Laurent executive, to head up “special projects” and report directly to Apple CEO Tim Cook. Combined with rumors of a gold iPhone in the works and talk of a brave new color palette for its new tech products, Apple could be setting up for a “fashion war” with Google and the hordes of companies hoping to offer smart watches by 2014. This fashion war won’t be about operating systems and product specs — it will be about design, aesthetics and the pursuit of cool.

The only problem with this scenario, of course, is that wearable tech still has Naked-Geek-in-Shower Syndrome. The single most viral photo of Google Glass to date is a photo of a naked tech blogger in the shower – a photo that gave rise to the term “Glasshole” and turned Google Glass into a topic for parody on “Saturday Night Live.” Suddenly, Google Glass was as nerdy as having a pocket protector once was. When people think of Google Glass this fall, will they think of a naked guy in the shower, or will they think of wonderfully glamorous supermodels walking around in Google Glass while contemplating the minimalistic future?

If that was the only obstacle facing Google and Apple – getting over the “nerd” factor – then it’s safe to assume that Anna Wintour and The September Issue would be enough to get them over the fashion curve. Hand out Google Glass to a bunch of supermodels, crank up the Madonna, and have a party when it’s time to report quarterly earnings to investors in 2014. (And, by the way, that also looks to be the strategy of Marissa Mayer and Yahoo – her “sexed up” photo in The September Issue is also attracting attention).

The problem is that Google Glass also has a really icky police surveillance state problem. After an initial euphoria about Google Glass and its ability to augment your future, the pendulum seems to have turned against Google Glass. It’s not just that random strangers may be snapping photos of you without you knowing it, it’s that the police and the government may be soon be monitoring your every move. As a result, Google Glass has had a tumultuous past few months, in which it’s been banned from bars, from Vegas casinos and other establishments where privacy rights trump the potential of the minimalistic future.

It’s hard to bet against the likes of Anna Wintour and Diane Von Furstenberg when it comes to the fashion zeitgeist, of course. Maybe Google Glass will continue to appear on runways around the world, other fashion designers will  jump at the chance to design with Google, and other luxury brands will embrace Glass as well. Who knows, maybe as with just about any other product in the retail world, a bunch of glamorous and impossibly thin supermodels can convince us to buy a product, thereby transforming wearable tech into the fashion statement of the year.