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Would caution that the experience may also be wildly different depending which tailor he decides to work with.That's great, but in my experience it's just more fun to do it in person and if one is struggling with the huge amount of choices you have, being in a real store is great. When I commissioned my first pair of trousers, my tailor was able to bring me some pairs I could try one that featured whatever I was thinking about. I couldn't have done that online. I recently commissioned some shirts with T&A at one of their trunk shows and that feeling of being pampered and being the center of attention, in addition to the copious amounts of complementary drinks, was amazing and could not have been done online.
I am not saying you can't have a good experience online or should never do it online, but OP is popping his cherry and I believe that should be something special, not a glorified Zoom call
Obviously everyone has their own preferences but I prefer to work with independents which often means a more normal hotel room than a large suite, usually not 5 stars, a shared workspace or basement workshop, I’ve been measured in a garden sitting on plastic patio furniture, etc.
I’ve also seen pretty lousy MTM passing itself as bespoke where they’ll make you the center of attention and hand out all the drinks you want. The window dressing isn’t all important to the experience or the end result.