Cheaney Chelsea Boots Out Of Box
January and early February saw me traipsing through Asia. I had a chance to hit up some great rooftop bars, check out some cool markets, catch a kickboxing match, and even get a solid case of food poisoning. What I wasn’t expecting to do, albeit virtually, was pick up a pair of English-made Chelsea boots and have them shipped to my home in the USA.

It was a Christmas gift to myself. Sue me.

To call myself a footwear enthusiast would be an understatement. I’m more of a footwear junkie, perhaps a footwear nutjob. I have a shoe collection that’s 130+ strong, but have never owned a pair of Chelsea boots. I have a rather large foot and have never found a pair that I thought looked good on me. Imagine my excitement when I found this pair that was beautifully made, exceptionally well-constructed with a Goodyear welt, and, ahem, handsome to boot. The difference maker with these boots for me was the pebbled leather adding texture, and the maroon side elastic breaking up what would be a sea of black on my US size 14 EEE foot!

These boots are fantastic for the fall and winter, providing superior style and versatility to my wardrobe. With jeans or trousers, with a suit or casual coat, these boots will do the trick.

As with all of “The Ensemble” posts, I like to highlight not just the item featured, but the entire outfit and why I put it all together. Enjoy.

Black Pebbled Leather Chelsea Boots – By Cheaney & Sons

Joseph Cheaney Boot Box

Cheaney & Son Dust Bags

On shoes this high-end, even the dust bags are beautiful.

Cheaney Insoles

Hand-written manufacturing information is typical of benchmade shoes like these.

The attention to detail here is top-notch. Note not just the beautiful embossing, but also the all-around stitching and tacks in the heel.

Black Chelsea Boots With Red Elastic

The reddish-purple elastic gore is a fun detail that makes these boots unique.

These boots are the real deal. Like any well-made pair of footwear, they come with their own dust bags to protect them while stored. These are particularly handy while traveling, as they protect the shoes from each other and protect your clothes from the shoes. The reddish-purple gore gets big-time style points, and the pebbled leather is both comfortable and functional; while not fully waterproof, pebbled leather tends to perform better if you get caught in a surprise rain.

Most important is the fact that these are constructed with a Goodyear welt. That makes these boots rather easy for a cobbler to resole as they age and wear down, meaning that I will get a lifetime of wear out of these boots for minimal further investment. Anytime you can buy shoes made with a Goodyear welt, I strongly encourage you to do so.

How #TheEnsemble Works

The idea behind this ensemble was simplicity and subtlety. A navy jacket, charcoal trousers, and white French cuff shirt serve as a blank canvas on which you can draw a wonderful illustration with accessories and footwear. The devil is in the details of this outfit, as I’ll explain further below.

Paul Anthony The Ensemble Chelsea Boots

The beauty of a black Chelsea boot is that it can go with just about anything. Here I’ve paired them with charcoal flannel trousers and a dark navy blazer, both from Benson & Clegg. The blazer has the house’s signature turn-back sleeve cuff, a detail rarely found on blazers. It also has a killer lining that showcases the various neighborhoods and areas of the City of London, my hometown. The dotted tie and floral pocket square add visual interest. Lapel pins are the Coat-of-Arms of the City of London and the Union League member rosette.

I could just as easily wear these boots with denim, a sweater, and casual sport coat. For a guy who’s got more of a rock-and-roll style, jeans and a leather jacket would still work beautifully with these boots.

Highlighting More Accessories

Black Pebbled Leather Chelsea Boots

Copy of Financial Times sold separately.

No outfit is complete without accessories and I pulled out most of the stops with this one. I mentioned the lapel pins, pocket square, tie and tie bar above, but here we can see the watch, cufflinks, and an even better shot of the turn-back cuff of the blazer. This ensemble can take me from the office to drinks after work, or even a nice dinner in town.

#TheEnsemble Items

  • Chelsea Boots: John Cheaney & Sons
  • Blazer: Benson & Clegg
  • Trousers: Benson & Clegg
  • Shirt: Benson & Clegg
  • Tie: Dapper Lapel
  • Tie Clip: Dapper Lapel
  • Pocket Square: Kaye H Textiles
  • Lapel Pins: Benson & Clegg button, Union League Member Rosette
  • Cufflinks: Benson & Clegg
  • Watch: Vintage Omega Seamaster on Hadley Roma strap

As always, your comments are more than welcome below, and we look forward to sharing the next #TheEnsemble with you.

About the Author:

Paul Anthony is the founder and creative director at Bespoke Unit. He has had a life long affair with design, watches, fragrance and clothing. Originally from England, he now lives in the USA splitting time between NYC & Philly. Favoring "British Style", but has an overall eclectic taste.


  1. Mike Oxmanchael February 7, 2017 at 1:22 pm - Reply

    The color of the elastic sides on those boots is awesome.

    • Paul Anthony February 7, 2017 at 4:49 pm - Reply

      Thanks, game changer!

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