The Chelsea Boot

321CEA74-4C40-4EA2-9FD8-4124AD9B4C0FWe called them ‘riders’ in my distant youth. All the tough kids in school wore Doctor Marten’s boots but the cool kids wore riders. My first pair were reddish brown, for ‘best’ only and I was chuffed when my Mam bought me them, summer 1977, aged 12. Unfortunately they didn’t get a lot of wear as I quickly grew out of them.

I had another pair about a year later in black for school. I surrounded the rims with so many ‘Blakeys’ that the clip-clopping sound they made in the school’s cement-floored corridors became my trademark.

After I discovered the Mod style I went on my first holiday without parents to London following O-levels, aged sixteen, in July, 1981. I came home with a pair in electric blue suede from Shelley’s on Carnaby Street. I never saw anyone else wearing boots like that before or since. I’ve always liked shades of medium blue (cobalt / royal / electric) so they went well with other items I had, and made my black suit really pop. I wish I could find a photo I remember of me wearing black suit, white shirt, electric blue suede boots and electric blue suede tie, taken at my sister’s wedding reception in August, 1982. I had another pair in black suede in the sixth form.


Due to the English weather I finally gave up on suede, and probably grew tired of Chelsea boots too, I never really looked at them for decades.

In 2010 I went to England with my other half. Besides visiting my home town we walked all over London, Edinburgh and Paris. Throughout the trip I did all that walking in a pair of black three-holer Doctor Marten’s shoes (no yellow stitching). On reflection, I decided that they covered the comfort factor well enough, but fall somewhat short on the style front. This got me thinking about what would be the most versatile footwear, which can be dressed up with suits, dressed down with jeans, be comfortable for hours of walking and be reasonably weather-proof. A good choice to travel with, which would avoid the need to travel with several pairs. After much thought, I couldn’t come up with a better choice than Chelsea boots.

I understand that Chelsea boots first appeared in Victorian times, the mid-nineteenth century to be more precise. I was surprised to learn that rubber could be manufactured to make the elastic side gores as early as that. I assume that their popularity stemmed from being an easier alternative to the button sided boots of the time. I’m not sure where they got the equestrian pedigree from, but as horse riding was a popular pastime for the upper crust, they may have made an easy transition from being a walking boot to being used as a riding boot too. I also have a pair of jodhpur boots which I believe share a similar pedigree but fasten with a strap around the upper ankle in place of the elastic gores. Zip-sided boots reek of the 1970’s to me, the decade that style forgot, and I can’t look upon them with any kind of admiration. Chelsea boots are of course associated with The Beatles during their cute suits and mop-top era, which may have turned off some of the original Mods who didn’t want to be associated with anything so mainstream. I tend to think of ‘Beatle Boots’ as having a central seam and higher stacked Cuban heels, although I’m sure that they got through several styles during that period.

The trick with Chelsea boots is to get the last shape right. Not too pointy, not too bulbous.  I tried on pairs from Crockett and Jones ($680 but too wide-fitting) and Frye (too rustic) and after further searching came across a pair that fit the bill in Aldo for $160. These came with single leather soles. I would have preferred rubber soles for grip and wet weather, so took them to a cobbler and got Vibram rubber soles added for $30 which are thin enough to add no noticeable bulk.


So here they are. Not perfect, but very close to what I was searching for, at a reasonable price. I’ve already worn them for a business trip for which their weather defiance wasn’t required but their versatility was appreciated. Time will tell how much more use they get.

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