Jackie III R Chukka Boot in Mahogany Grain Leather

  • £495

Jackie is one of our most iconic designs and has been reimagined in various colour options throughout it's long history as one of our most traditional designs. Chukka boots offer a great versatility to the wearer as they are equally suitable for casual wear as they are for more polished looks. Traditional in design, the three eyelet derby is stacked on a Goodyear welted studded rubber sole for practicality and are fully handcrafted in our Northamptonshire factory.

Last Shape: 125 | Fit: F (Average), G (Wide), H (Extra Wide) | Sole: Studded |
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       These statistics are gathered from customer reviews and returns data.

       For more information about size & fit visit our Fitting Guide

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UK Delivery

Order ValueDeliveryCost
£0.00 – £29.99
Royal Mail
2–3 days £4.00
£30.00 – £149.99
DPD
1–2 days £7.00
£150.00+
DPD
1–2 days FREE

International Delivery

We ship worldwide to over 175 countries.

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Not going to be home? Don't worry, have your parcel delivered to the nearest DPD Pickup point.

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Returns & Exchanges

If you are not satisfied with your purchase for any reason, or if you simply change your mind, you can return the item(s) to us within 30 days of receipt.

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Showing 10 of our total 14 reviews, with an average rating of 5 stars. Read all 14 reviews for Jackie III R Chukka Boot in Mahogany Grain Leather.
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Review Summary - 5 out of 5 based on 14 ratings.
June 12, 2024 | Peter
Versatile Chukka Boot

I bought the G fit version through a third party retailer and am broadly happy with the boot. It’s great to have a wide fitting option. However I’m not sold on the new studded sole. I find it less comfortable than Danite, for two reasons. One is the compound seems harder than Danite and the second reason is this sole unit is not quite as thick when put up against my older Danite soles Cheaney’s. Therefore I feel more of the ground under my feet on this sole unit. Otherwise a lovely boot but in future I’ll be keeping to boots on a Commando or V lite or Brit sole.

Cheaney Shoes Ltd
April 4, 2021 | Gards
Fantastic boot

Lovely supple leather which oozes quality.
Boots felt pretty comfortably upon initial wear and after about 12 hours or so of sitting and walking around at home, now feel like slippers.
A significant investment but I'm sure I will get years of wear out of these boots and I highly recommend them.

Cheaney Shoes Ltd
December 16, 2020 | Nihal Fernando
Fabulous shoes esp in the G size

I already have two pairs of formal black Cheaney shoes bought in 2008 (liked the first pair so much bought an identical second pair) that I have resoled for the third time early this year. So you may say I have a soft spot for Cheaney shoes. However, on seeing these shoes, and looking at the reviews and seeing their fit to my needs for a winter pair of boots, I pulled the trigger and have not regretted the decision one bit. What a fantastic fit especially in the wider G fit for me. Best wishes and don't hesitate, these are good value for money even if they are £380 as they will last many years and you won't have to buy a pair for a couple of winters at a time. I will write more about this pair in 2032!

Cheaney Shoes Ltd
May 4, 2020 | Ian Fraser
Classy chukka

I already had a pair of Jackie III boots in the Dark Leaf; they were a size 10 F fitting, and pinched quite badly because they weren't quite wide enough. I saw these size 10 G fitting boots in the Mahogany, and bought them. The colour is fantastic, a rich dark brown, and the G is much more comfortable - in fact I could have probably gone down to a 9.5. They're really comfortable, and a great looking boot.

Cheaney Shoes Ltd
April 26, 2020 | S Bramwell
Stylish, comfortable boots

I've not had them long but I can tell already that they will break-in quickly and be very comfortable. They are well made and the leather is excellent. My feet are wider than an F but narrower than a G so I ordered the G and together with a thicker sock are a good fit.

Cheaney Shoes Ltd
December 1, 2018 | Richard J Turner
The elagance of mahogany grain laether.

This is my third pair of Cheaney footwear and as ever a delight to wear. A great look and a lovely feel. However after only about four times of being worn the lace is starting to fray. I wonder if it is worth supplying a spare pair of laces? But don't let this put you off from buying a pair. Your feet with thank you and your style will become more sophisticated.

Cheaney Shoes Ltd
October 19, 2018 | Alex
The Ultimate

It's always been a personal quest to own a pair of Cheaney's and these certainly didn't disappoint! Comfortable and stylish from out the box, I virtually live in these (ok I do have two other pairs) for going out, interviews and casual times. Highly recommended!

Cheaney Shoes Ltd
June 30, 2018 | Philip Poitier
Perfect!!

Great shoe! I get compliments every time I wear them. It's casual but dresses up everything I wear. Second 125 last in my growing Cheaney collection and the fit is great on my F to G "tweener" feet. Plus again, the shape of the shoe really looks classy! Only downside is it's only available in a UK 13 fitting in the mahogany pebble grain, otherwise I'd have one in each leather!

Cheaney Shoes Ltd
April 8, 2018 | Philip Worrell
Quality, style & service

First pair of Cheaney footwear and probably not my last.
Looked at many chukka type boots from premium manufacturers and the Jackie 111 R in mahogany grain leather was the best for me. Was unsure of the fit and John at the factory was a great help. Like everything about the boot quality, style, finish and colour.

Cheaney Shoes Ltd
March 3, 2018 | Dee
Great quality and classic!

Brought these for my husband for his birthday after buying him the suede ones last year which he hasn’t had off him. Great quality, beautifully made and a looks a cut above the mimics on the high street. Slightly expensive but worth it.

Cheaney Shoes Ltd
Chukka Boot

Chukka boots have been around for a long time and they are said to be originally from India. Of course, they were mostly worn by the British Army who were based in India at this time and more commonly worn by off-duty polo players. The name “chukka” is said to be derived from the playing period in polo which is called a 'Chukka' or a 'Chukker'.

A Chukka boot can be characterised as a low ankle boot and usually features two or three-eyelets, an open lacing system and a rounded toe. The chukka boot's appeal lies in its ability to be worn with a large array of outfits. Reliable and versatile, chukka boots are suited to all seasons.

STYLE GUIDE

Chukka Boot
Last 125
Last 125

Developed in 2011 to coincide with Cheaney’s 125th Anniversary, the 125 last has a classic but exceptionally versatile shape. Featuring an elongated almond toe and a sleek silhouette, this is English style and tradition at its best. The 125 is one of Cheaney’s most revered and celebrated lasts, playing host to a myriad of styles.

FIT ADVICE

  • Fits true to size
  • Accomodates larger insteps

LAST GUIDE

Studded Sole
Studded Sole

The studded rubber sole, a hallmark of English Goodyear Welted footwear, features a distinctive tread pattern that is both eye-catching and functional. This design prevents soil retention, making cleaning effortless. Additionally, the sole is highly durable, long-lasting, and provides exceptional comfort for the wearer.

Sole Code R

SOLE GUIDE

Repair Service

With proper care, Cheaney shoes & boots will give comfort, value and service over a considerable time. However, if after wear you wish to extend the life of your Cheaney footwear, we are able, because of the quality of the materials used in the original manufacturing process, to offer a sole & heel repair service. With skill and care, our crafts people rebuild the shoes, using genuine components and reconstruct it to its original specifications.

FIND OUT MORE

Calf Leather

Calf leather forms the foundation of a large majority of our styles due to its classic appeal, hardwearing nature and adaptability. Our signature leathers are sourced from tanneries within Europe. Burnishing refers to slightly darker shades being applied to the shoe, specifically around the toes and heels - meticulously done by hand in our factory, burnishing gives each shoe personality and shows off the leather beautifully.

LEATHER GUIDE

Calf Leather
Last 125
Last 125

Developed in 2011 to coincide with Cheaney’s 125th Anniversary, the 125 last has a classic but exceptionally versatile shape. Featuring an elongated almond toe and a sleek silhouette, this is English style and tradition at its best. The 125 is one of Cheaney’s most revered and celebrated lasts, playing host to a myriad of styles.

FIT ADVICE

  • Fits true to size
  • Accomodates larger insteps

LAST GUIDE

Studded Sole
Studded Sole

The studded rubber sole, a hallmark of English Goodyear Welted footwear, features a distinctive tread pattern that is both eye-catching and functional. This design prevents soil retention, making cleaning effortless. Additionally, the sole is highly durable, long-lasting, and provides exceptional comfort for the wearer.

Sole Code R

SOLE GUIDE

Repair Service

With proper care, Cheaney shoes & boots will give comfort, value and service over a considerable time. However, if after wear you wish to extend the life of your Cheaney footwear, we are able, because of the quality of the materials used in the original manufacturing process, to offer a sole & heel repair service. With skill and care, our crafts people rebuild the shoes, using genuine components and reconstruct it to its original specifications.

FIND OUT MORE

Our Guides Handy Tips, Style Advice & Information
How our shoes are made

For over 140 years, we've been crafting exceptional footwear in the heart of England's shoemaking county. Discover the skilled craftsmanship, traditional techniques and attention to detail that go into making every pair of Cheaney shoes.

Size & Fit Guide

Nothing compares to visiting a Joseph Cheaney & Sons store in person and receiving a fitting consultation from our expert staff. However, we understand that visiting a store isn't always an option for everyone so we've put together this guide to help you choose the correct size

Our recommended polish & creams

If you’re wondering which products and colours we recommend to look after your shoes. We've put together this guide; you will find a comprehensive list of our current leathers with the recommended products. Feel free to use some creative licence within reason.

Wedding Shoe Guide

Regardless of the style or cut of your suit, choosing the right colour shoes for your outfit is crucial to achieving a sophisticated and well put-together end result for your big day.

Style Guide

What's an Oxford and how does it differ to a Derby? How is a Brogue different to a semi brogue? Discover the range of different styles of footwear we design and manufacture in our Northamptonshire based, UK factory and learn more about their origins and history. 

Polishing Guide

Polishing, if done regularly, shouldn’t take up too much of your time and won’t be at all arduous, as long as you do the basics right. Discover our top tips and step by step video of how to keep your shoes looking their best and what the best care products are to use.

Sole Guide

Have you ever wondered what the letter(s) B, C, D, R, GV means in the name of the style of footwear; well it references the sole used. Gain insight into the different types of soles we use on our footwear, from a traditional leather to heavy duty rubber sole, there is a sole for every occasion.

Last Guide

The last is the 3-dimensional form on which our shoes are constructed. The shoe proportion, shape, fit, width and character start with the last. If you can identify the last that suits your foot, all the shoes or boots built on that last will fit well. 

Leather Guide

We only source high-grade leather from the best tanneries in the UK and abroad to produce our footwear. Our collection includes various leathers and we are constantly discerning new treatments and characteristics to expand our unique collection.

How to care for suede shoes

The common myth is that suede shoes are notoriously difficult to keep looking their best. However, don’t be put off as this really isn’t the case; whether it’s a new pair or you need to rejuvenate an exsiting pair, we’ve created a definitive guide on how to care for and protect suede shoes.