It depends...
I own one hat made by Art, an Akubra, and about a dozen vintage hats, so my knowledge is limited. Since I don't let a lack of knowledge interfere with stating my opinion, I would say that we are dealing with apples and oranges. An analogy can be drawn to vintage and modern cars. You would not expect the same refinements in a vintage Mercedes Benz as you would in a new Mercedes. The wood and leather in an old Mercedes are different than in a new one. The wood and leather in an old Mercedes may be incredibly luxurious, if the car were kept well or well restored. The wood and leather in a new Mercedes would be pristine because it is new. You cannot say whether the wood and leather in an old Mercedes is better or worse than in a new Mercedes until you know what the condition of the old Mercedes wood and leather is.
Assuming that the wood and leather in the old Mercedes is pristine (NOS), then you still don't have an answer to the question of which is better, the old Mercedes or the new. That is a matter of taste. There may be some objective standards but your preference is personal. Same with old and new hats. There are some vintage hats that are pristine and some that are beaters.
The new Mercedes is likely to have better performance and handling since science moves forward. The old Mercedes will have a "classic" look. How much each of those are worth is a matter of personal opinion. While a fine custom hatter can reproduce the look of a hat, he cannot reproduce the patina of age. Like wood, felt changes over time, even if the hat has been in storage for years. The old Mercedes has something the new one does not have, age. For some of us, owning an old hat means more than having a head covering. I think about the times the hat has gone through, the history that has been experienced by the owners, who owned it before me, etc., etc., etc.
My old hats are wonderful. They have seen World War II, Korea, Vietnam. man setting foot on the moon and the turning of the millennium. Two of them were owned by a nationally ranked rifle shooting champion, one came from the estate of an industrialist.
With my hat from Art, I write the history. It is so well made that when I pass it on to the next generation, I hope they will say, "This was my uncle's hat. Let me tell you about some of the things we did together." I don't think they will feel the same way about my vintage hats because they just "passed through" me. My Art hat has my initials in it and always will unless someone changes the sweat band.
So to address the question directly, "Which do you prefer, vintage or custom?," I can say firmly and without equivocation, "Yes."
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