I recently had these boots made bespoke by Roberto Ugolini in Florence, and they have turned out very well. I have two reflections about bespoke shoes off the back of them.

One is that I am increasingly specific about what I need in terms of fit, and it seems to be paying off. 

I make it very clear that I only get pain with shoes in two places. One is the outer edges of my toes (little toe joint, little toe itself, fourth toe) and therefore I need width in that area. It’s what kills me on narrow shoes like my old Corthays and, more significantly, bespoke shoes in the past. 

The other area is the top of my big toe, which is rather larger and taller than the others. Any shoe that is too tight across the top will bite on that big toe and be horrible. 

Beyond that, I’m golden. There are many other areas a shoemaker has to get right of course, but these are less crucial. It’s in those two areas that makers have fallen down over the years.

When I talked to Roberto, I made this clear. At the measurement stage, at the fitting stage, I swallowed that natural English reticence and communicated rather specifically.  

When I was younger I didn’t, and a lot of those shoes were just too small for me. Partly it was awe at the bespoke process itself - the work these makers were going to do on my behalf, the combination of skill and strength. But just as importantly, I didn’t have confidence in my own opinions.

The shoes felt tight, sure, but wasn’t that how it was meant to be? Even when the results were sometimes painful, they were not that much more so than ready-to-wear could be - just in different places. 

During the pop-up in London recently, I had two separate conversations along the same lines - readers saying they’d tried bespoke and it wasn’t what they expected, but they weren’t confident of their opinion. 

My lesson is not that everyone should speak their mind and shoemakers should obey them. (I’ve heard enough odd opinions to sway away from that.) But instead, that it takes time to know what you need.

I should have learnt faster, certainly, but I think everyone needs time. No one comes to this with any experience, and we don’t have friends or family that have been through it either, as in older generations. Shoemakers themselves might also benefit from talking about this to customers.

And it adds to the argument I made last year, that bespoke shoes really make sense as a long-term thing - over years and pairs, often with the same shoemaker. I have to cover everyone; I wouldn’t necessarily recommend anyone else do the same. 

In fact it almost feels unfair to compare this Ugolini experience to those older ones with other makers, given how much I’ve changed. 

But that shouldn’t take away from how nice the boots are. I was particularly pleased because I’d heard a couple of negative experiences from acquaintances, but mine were good at the trial stage, were well executed, and the style was exactly what I was expecting. 

That last point is my second takeaway: whenever possible, commission shoes that you have already seen in person. 

Roberto has a decent range of shoes and boots on display in Florence, and I picked a specific chukka, then picked the suede to make them in (from an actual hide, pleasingly). I knew what to expect, and so it was much more likely the result would meet my expectations. 

When I look back on bespoke shoes in the past, I so wish I had done that more. 

My Cleverley double-monks, for example, were a real mismatch of shape and style - too elongated and fine for that leather and style. We did talk about making the shoe rounder and more casual than the previous pair, but the salesman and I were clearly talking about different things, because the changes were very small. 

You’d think I’d be more relaxed these days about making mistakes with such commissions, given I have a fair few bespoke clothes. But it actually annoys me more, feels more frustrating. Perhaps it’s the waste; perhaps the thought that I should know better. 

The one thing I was a little unsure of with the final boots was the sole edge - which tellingly, is the one thing I changed from the pair on display. 

I went for a dark colour, and a lighter one would have been a more natural fit for the snuff suede. But I’ve found the difference small, and it means the shoes are slightly easier to wear with things like dark denim. 

I’ve also found the boots a nice match for anything that has a slight Western feel, as this clothing combination does (full details on that here). The shoe has that slightly pointed almond shape that we discussed on this original piece on my roper boots. 

Elsewhere, there are small points where you could point out that the finishing is not quite the same as the very top bespoke, such as along the welt line. The work overall is good though, and the price also lower than many makers, with shoes starting at €2300 and these boots costing €2400 (both excluding VAT). The couple of scratches on the upper are also my fault - or rather, natural signs of wear. 

The boots have beautifully made boot trees (that's the handles showing out of the top), a box made with local Florentine paper, and I rather like the way the laces are finished with simple knots. Those things are probably in descending order of importance.

Overall I’m very pleased but also slightly relieved - relieved that the boots fit well and I will wear them for many years to come. Hopefully I’m getting better at commissioning them, even if it’s taken a while. 

(Oh and this experience probably weighs against the idea of making shoes based on scans of the foot, at least for bespoke. The challenge of bespoke is not knowing what the customer’s foot looks like.)

Roberto currently travels to New York, Seoul and Japan for trunk shows.