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Only explanation I have is that the quest dialogue is bugged and the tailor doesn't have the clothing at the point we've reached. In every other similar instance where you need to collect an item, it's usually retrievable some other way - but the tailor does not have the clothing either on him nor in his chest, so I assume it's already been given away even though the actual story/dialogue that has led us to this point does not indicate this.
Time to go find that guy that was meant to be the waiter in the first place, even though I don't remember who or where he was lol.
If someone wants to try since I haven't done this yet can we see if its something pickpocketable? Or in a chest near the tailor?
Not saying you're wrong (I feel like the original waiter did already pick up the clothes) but the quest is definitely bugged that maybe if you do things in a certain particular sequence, the original waiter has already picked up the clothes but tells you to go get them from the tailor anyway instead of offering them to you.
If thats the case I would just steal them from the chest if its bugged or reload from a previous save.