I've been buying second-hand bespoke shoes on eBay for a while now. I gravitate towards the "big three" London makers (Cleverley, Lobb, Foster & Sons).
As it happens, buying bespoke shoes that were made for somebody else tends to be a non-starter in most cases since the fit of a bespoke pair is rarely standard enough for a random wearer (i.e. me or you). Their greatest strength for the original owner - the very specific fit - becomes their biggest liability for the next (greatest hypothetical strength at least - there are plenty of horror stories of poorly fitting shoes out there).
I've bought and sold probably 30 pairs and kept two that fit me well enough. And this is buying pairs that look like the outsole measurements are in the right ballpark for my size, not just random shot-in-the-dark purchases. Best to keep your expectations around the success rate modest.
As an added factor of complication, bespoke shoes can be radically differently sized between the left and right foot, whereas at least a RTW pair gives you a consistent base to work from. I wrote about the quirks of buying used bespoke here, but to concisely summarise - it's mostly a ball-ache and pain in the arse. Proceed with caution. This is not the way to build up the basics of a shoe wardrobe.
It's the strange allure of the makers and the fact that they can often be grabbed relatively cheaply that makes me keep going back for more. It's a look into a world that I'm unlikely to be able to afford for a long time, if ever - most of these pairs retail somewhere from £3k - £5k (which may seem bizarre to you given how largely unexceptional they appear in most instances, but the diminishing returns argument can be had another day).
Still, I only buy when I can be pretty confident that I'll be able to sell on for more, so it keeps the whole enterprise pretty cost-neutral (or even positive.
John Lobb St James Quarter Brogues These were some wiiiiide boiz - the Derby lacing could accommodate a G width, maybe more. Other than that they are pretty much perfect size in terms of the footbed dimensions, so an ideal example of why outsole measurements mean diddly squat in terms of gauging fit. They could have fit pretty well if I jammed a rolled-up sock in the instep.
John Lobb St James Black Derby
One of the two pairs I've actually kept - not an eBay purchase, but rather from classicshoesformen.com. As such, they were rather pricey (though they were in new condition), but the fit is really good, and as far as "safe" dress shoes go they are perfect. Far more useful to have in the rotation than black oxfords, in my opinion.
John Lobb St James Snuff Suede Monkstrap Another pair that, on paper, should have fit well, but on the foot were agonising after a few steps. The tobacco-brown suede is lovely though. I'd love a pair in this style that... you know... fit properly. I think they would be really versatile, and the single monk is a less peacocky aesthetic than the double.
G.J. Cleverley Snuff Suede Lazyman
Not dissimilar to the JL pair before, these also included the bespoke trees (a surprisingly rare inclusion on eBay, they are often sadly separated from the shoes before sale). They were a really nice pair of travel trees, hollowed to within an inch of their life so they were incredibly light. I really struggle with lazyman and loafer fit though, and these were no exception. Too loose and too tight all at once.
G.J Cleverley Wingtip Imitation Brogues
I loved these shoes - the fit was fractionally off, but noticeable enough that they would never be comfy. Probably the finest finishing on any pair on the list - the imitation broguing was exquisitely done, and the colour of the leather - a plummy dark brown - was very appealing. They also had the nicest sole finishing, especially at the waist, which otherwise tends to be very flat and conservative from these makers.
Foster & Son Captoe Oxford
Probably the oldest pair on the list (or if not, they had a very hard and abusive life). Pretty polarising design details with a really square toe, they are if nothing else a good photographic example of what patina looks like.
Foster & Son Single Strap Brogue The newest pair, which spurred me to put together this post. No review on the blog yet, but pleased to say this pair are an excellent fit. Picked up for a song on eBay as they were in a bit of a sad state, but I think the after photo (above) and the before photo on the eBay listing (below) show the difference a bit of cleaning, conditioning and polishing can do. Chunky but rather pleasing, all things considered.
Conclusion
So that's it really. Think the only lesson here is don't buy second-hand bespoke shoes online unless you have 1) a lot of patience to restore them and 2) accept that you will probably need to sell them shortly afterward.
If you want to know more about bespoke shoes from somebody much more qualified and competent than me, check out bespokeaddict on Instagram. His collection is incredible, and he does a lot of work to shrink or stretch shoes to his perfect fit.
Great to see bespokeaddict mentioned. A YouTube video if his provided me with the know how to restore a pair of my Dad's shoes he bought in the late 70s or early 80s but he'd stopped wearing them as the leather was cracked. Turned out to be cracked layers of polish.