A friend called Michael Friedberg recently, thrilled that he had just bought a rare 50th anniversary watch at a local boutique. Michael shared his joy and asked him how he acquired it – which led him down a rabbit hole of boutique madness. Here he shares his frustrating experiences trying to buy a luxury watch today.

You can like everything, but you can’t buy – or keep – everything! Inevitably, the choices involved lead at times to regrets; for GaryG, along with many of his pals, the sadness is much more often about pieces they sold too soon or failed to buy rather than pieces they were sorry about buying in the first place. Here’s a story of shoulda, woulda, coulda.

While GaryG thinks it’s all the more impressive that designers continue to delight us with new looks, many watches are often very similar. And trying to describe the slippery slope from vague resemblance to outright theft is not a simple task. So he begins down at the lower end of the grade with so-called homage watches and moves up the GaryG Styling Statute of Limitations from there.