Originally Posted by Holdfast
A promise & threat all rolled into one. Excellent.
A fun selection, and thanks for the include. Not sure which is my favourite though this week. A lot of very good looks but nothing that stood out as totally stunning from your selection. Probably the first "Neo in Flight" example - it's the most thought-through/composed look I think.
On the PGTOTW, the easy answer is to say bespoke is always the answer. But in truth, PG I'm guessing probably has access to cheaper bespoke than I would. And one does need a fair few shoes in order to have variety for different looks (OK, the foo would disagree with that, but that's because he only wants one look. Oh, and he's nuts.
Having enough variety starts to get expensive with bespoke shoes even faster than it does with suits or jackets.
I think the answer for the PGTOTW (nice acronym btw) varies from person to person (and perhaps more importantly from income to income). If you enjoy new things a great deal then bespoke is probably not the answer. Imagine the expense of Portnoy's collection from G&G bespoke (not that there isn't an income for which it's appropriate, just that $3,000 x even just 50 pairs of shoes is a very nice car). If, on the other hand, you want the one shoe then bespoke seems more sensible (at a very reasonable honda fit for your six pairs).
I think generally once someone has a certain number of pairs they'll head bespoke and only rarely look back.
If you were planning to go entirely bespoke from the beginning I think you would run across the issue of what to buy first. Bespoke takes time and you'll need something to wear for the next six months/year. In terms of need, I think there's probably only formal wear, black captoe, brown captoe, brown brogue (or half brogue) of some variety and a country shoe. And even that could be cut to formal wear, black captoe and brown half brogue (please don't ban me from the forum). I suppose if I had to start over I would probably buy only a black wholecut and a brown half or quarter brogue and then order two pairs of bespoke shoes every year. For better or worse, that ship has sailed but it's certainly an interesting thought.
As a general answer to the question, bespoke generally looks better to my eye as more care is taken in production, but that difference matters very little in anything other than close up camera shots, actually holding the shoe and one's own imagination (oh right, and fit).