“Sir Winston” is my interpretation of Sir Winston Churchill as a hand welted shoe.

This post is a summary of the finished shoes – in the construction post, I describe how they were made.

It’s clearly a formal shoe, intended to be suitable for a venerable statesman.

The uppers are decorated with some restrained broguing on the toe caps. All the upper leather is Weinheimer boxcalf – with a german connection that felt appropriate.

The sock liners were chosen in a ‘colorado claro’ color, representing cuban tobacco. The choice of leather for these cigar-colored sock liners, fell on G.O.A.T.

As part of the ‘showmanship’ of Sir Winston, these shoes are ornamented with a closed outsole stitch and sharp fiddleback waists, made with vintage Rendenbach outsole leather from the closed factory.

The outsole seam is over-emphasized in the detail work, which I think gives it a rather ‘military’ feel, speaking to Sir Winston’s heritage.

The last shape features a distinct chisel toe. (The lasts are, of course, British.)

View of a seat (I put the top lifts on correctly this time):

Outsole edges:

This Weinheimer boxcalf leather is very playful in the light, even though it’s pitch black. One could easily be forgiven for thinking that the image below is of another pair of shoes entirely. It is however, indeed, the same black pair – just photographed under some broad-leaved trees in shadowed daylight. There’s no photo trickery going on – the green color of the leaves is just reflected naturally in the black shoes.

This image makes me want to re-make this shoe design, but with dark green museum calf for upper leather…

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I’ll soon be celebrating the completion of these shoes by lighting up their cuban cigar namesake. There’s a certain cuban cigar – quite rare due to the global shortage of cuban cigars – by the exact same name of “Sir Winston”. It’s hand rolled in the H. Upmann factory in Havana. The size of Sir Winston (the cigar) is by definition a “Churchills” (factory name: Julieta No. 2), meaning that it’s 7″ long by a 47 ring gauge (ca 178 x 18,65 mm).

Pondering which celebratory cigar to choose, there were several options to consider. The Romeo y Julieta “Churchills” was a close second, seeing as how it’s also named after Sir Winston. Furthermore, it’s known that Churchill himself smoked a lot of cigars by the Romeo y Julieta marca, and probably favored it in general over other brands. The date of the introduction of the actual vitola (cigar size and shape) “Churchills” by Romeo y Julieta is however disputed, and not historically recorded. It may have happened first in the late 1940’s or even 1950’s.

Romeo y Julieta of course also offers the Petit Churchills, the Short Churchills and the Wide Churchills nowadays, all of which were contenders for celebratory cigar. These are all great cigars in their own right, but they’re not full-fledged Churchills.

The Davidoff line Winston Churchill also deserves a mention. These are absolutely splendid, world-class cigars, and indeed worthy of the Churchill name. They are, however, not rolled in Cuba – which made me exclude them from the final choice. (When Churchill was around, there really only were Cuban cigars available as a premium cigar option. This has of course later changed.)

I could write an essay about this, but in the end, I felt that “Sir Winston” by H. Upmann was the winner, partly due to sharing the exact same name as the shoes, and still being in the official Habanos Churchills size. H. Upmann also make really great cigars in general, and this particular cigar is somewhat of a crown jewel.

But, I digress. You tell me: do these shoes look like something Winston Churchill would wear?

On a final note, you may have already realized, but for the sake of full disclosure: I’m inclined to like Sir Winston Churchill… He certainly remains an intensely controversial figure for many, and I am by no means saying that everything that the man ever did was purely good. Surely, it wasn’t. As is the case for all humans, there is darkness to unfold also in the depths of his character. At the end of the day, however, he did indeed save the world. For that feat alone, he has my reverence.

Disclaimer: smoking is very bad, so you really shouldn’t do it. Unless it’s cuban cigars and you obviously don’t inhale. In that case, it may well function as balm for the soul (while it may or may not kill you anyway).

Specs:

Uppers: Weinheimer boxcalf in black
Lining: 2 oz veg tanned baby calf in black
Insoles & shank cover: J&FJ Baker buffed insole shoulder, 7-9 iron
Outsoles: Vintage J. Rendenbach from the closed factory
Top lifts: Vintage J. Rendenbach (also no longer available)
Toe/heel stiffeners: 5 oz from Tärnsjö Garveri
Welt: natural welting leather from Leather & Grindery
Shank: Plastic