If Google Glass didn’t exist, guys in Silicon Valley would be having affairs or buying unsuitable motorbikes – or so claim the “White Men Wearing Google Glass” Tumblr and Twitter feeds, which mock the device’s associations with unfashionable male geekery.

Now Google’s flagship wearable is a step closer to shedding its unflattering image: high-end online fashion sites Net-a-Porter and Mr Porter have started selling Glass to UK shoppers, the first third-party retailers to do so.

They are stocking the snazziest versions designed by Diane von Furstenberg, in colours such as “Matt Ice” and “Shiny Elderberry”. Buyers not put off by the Starbucks Frappucino-sounding names can grab a pair – including clip-on sunshades and a little screwdriver to attach the quartz screen – for £1,250 for women and £1,120 for men.

Tech and fashion make for an uneasy mix, and not just because of programmers’ hunched and hoodie-wearing image. It is also because the computing that underpins technology is all about stuff that is quantifiable and definable – while fashion focuses on the intangible, the intuitive, how things look and feel.

Steve Jobs knew that just because something can be readily categorised and analysed, that does not make it the thing that matters most – an insight that helped him make Apple’s iPhone a success. That unpindownable je ne sais quoi is what Italian eyewear mogul Leonardo Del Vecchio is looking for when he says he could sell “millions” of Glass via Luxottica’s partnership with Google, if only the tech group would do “50 per cent of what they had done with mobile phones”.

But aside from design, Google’s high-fashion ambitions face a bigger hurdle, or at least the hypothesis of one: that the more socially invasive the personal technology, the more others want to know if and how it is being used.

Take smartphones. Part of why they have become acceptable on dining and boardroom tables the world over is that there is always the moment, obvious to someone else, when a user decides to swipe or tap. “Smart” bands like Jawbone and Fitbit have caught on partly because someone else’s wrist is something you can choose to ignore – plus it is their business if they want to know how many steps they are taking or hours they are sleeping.

The challenge with Glass, though, is that it is right there on your face, and that its capacity to analyse the world as you experience makes it an inescapable part of your real-life interactions. Taken together, these features mean Glass has to be both fashionably unobtrusive and obvious to others what it is being used for. After all, it is hard to imagine a world where everyone is entirely relaxed about the prospect of being filmed during intimate conversations or interviews with their bank managers, or their emotions read via algorithms so their credit risk can be assessed.

The irony is that the more fashion designers make Glass ubiquitous outside the white male “Glasshole” market, the creepier it potentially becomes – and the more the technology will need to signal what it is up to. That might be too great a challenge even for a company with the inventiveness of Google.

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