The Apple Watch was initially sold at fitting appointments in store, and I think that was important in establishing it as a normal thing to wear and even a fashionable thing to wear in some cases, and helped cement the product in the mainstream.
Tailored suits is another case where there’s a premium price, premium service, but a lot of friction. It’s not always bad.
They’re also probably supply constrained enough that the friction doesn’t matter for the first version or two.