A friend of mine started investing in good shoes around six months ago. I find it reassuring that I get such vicarious pleasure out of it: perhaps I’m not as self-centred as all that.
His first pair was a lovely set of mid-brown, cap-toe Derbys (above). It was a perfect first purchase – adaptable to casual wear, around the office and business meetings, with jeans, chinos and suits. Apart from charcoal they went well with all his suits, both grey and blue. I had a small role in this decision so it was a relief to see his delight in them.
(As well as his near-obsessive interest in polishing and general maintenance. This was a man more used to wearing trainers that only looked scruffier as you wore them. Little did he realise the pleasures of looking after leather shoes, restoring them and creating a personal patina.)

For his second pair, he was tempted with brogues in pale suede. But in the end opted for Oxfords in a hand-painted oxblood (above). Darker, sharper and smarter, they will go well with dark denim as well as blue suits, while retaining a little individuality.

Finally, he mentioned to me that his next investment, sometime next year, will likely be black whole-cut Oxfords. He already has one pair of black shoes (though not of the same quality as these others) so black was not his first choice. But he recognises that black is an essential for business in Britain, as well as elsewhere. So they deserve to be the next pair.

This seems to me like a great trio of shoes. Each will probably only be worn once a week, as the office is rather casual, so rotation won’t be a problem. Brushed after each use and stored with shoe trees, they should be the foundation of his smarter wardrobe for years.

I can see them in my mind, sitting proudly in a row. Perhaps that gives me a little too much pleasure. But having introduced him to the world of classic footwear, it’s great to know his non-work wardrobe now has a grown-up option, alongside beloved trainers. And at work he will look far more professional.

Indeed, it reminds me of a question another friend asked a few months ago – what to invest in when you begin working, and want to steadily look more serious, professional and ambitious? My top three would be:

1 – A suit that fits you. Good material tends to wear better rather than look tremendously better. So buy an inexpensive suit and have it altered everywhere so it fits.

2 – Buy decent shoes. This isn’t hard. In the UK just buy Loake, Barker or Cheaney to begin with, look after them well and trade up when you can.

3 – Buy good ties. Cheap ties look cheap. Get good ones, again look after them well and make sure they are tight to your collar.

Those three things will change your look from graduate to junior management. Buy shirts, socks and expensive suits later.

[The shoes shown here are from Lodger, before someone asks. Apologies to readers who are sick about me carrying on about the brand – but it was my friend’s choice not mine!]

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b mickey

Simon great post. I really enjoy your blog. Quick question: in tip #2 you recommend buying loake, barker, or cheaney in the UK. Which US brands are of equivalent value?

Dirk Moermans

Do you know the Belgian shoe brand Ambiorix?
Handcrafted since 1895


Good post, and advice, thanks.

Solomon Animashaun

Fantastic Blog Simon!

The Other One

Congrats on the Permanent Style blog top listing ….we’re huge fans of Mr Pask’s NY Times Mag blog ourselves.

Re: the post, if it’s still under debate, technically the first shoe pictured IS an Oxford because the facings are stitched across (where the shoe laces up). If these were not stitched then it would be a Derby. A Derby is a better choice if you have a high instep as you can leave the laces opened more or if your feet swell a lot during the day, you can loosen them off. Same goes for flying – the Derby would be a better choice.

Now, a New Year’s invitation to Mr Crompton… we’d like to invite you to our studio to see the new generation of traditional handsewn bespoke shoemakers in action!

Deborah, carreducker


Hi Simon, great posts as always.

As a striving young upstart in the legal profession I’m always on the lookout for ways in which to stand out from the crowd.

Unfortunately, as a criminal practitioner, the wages are not at the level as some of the city types so I have to pick and choose whow and where to spend my hard earned wages. I was wondering if you could possible answer me a couple of questions.

1. I am in desperate need for some new work shoes, namely a black oxford for which to wear most days, alternating with a brown brogue. I recently came across some Church’s that I was severely tempted to purchase as they were half price. Would this be a wise choice considering the fact that they are still over £150? Or should I stick with a pair of Loake L1’s at half the price for the time being? One of the worries I have with the church’s’ is that the leather soles may wear out far too frequently and thus end up costing more.

2. I currently wear T.M. Lewin shirts from the John Francomb range as it is impractical to wear double cuffs when visiting prisons etc…do you have a preference for any brand and style of shirt within this price range? e.g. alternatives such as Charles Twhyritt? Or should I even re-consider ‘Jermyn Street’ shirts for simple M & S?

Thanks for your time and I hope you can get back to me.

Anthony White

Dear Simon,
A question I wondered if you might help me with.

In four weeks, my wife and I are moving to London from New Zealand. I will be jobless, and seeking interviews with management consultant firms.

My question is about shoes. I have a half dozen made to measure suits in various navys and greys. In New Zealand, I have always worn them with dark brown and chocolate coloured shoes. Interviewing in London, should I play it safe and buy some black oxfords?

Kind regards,
Anthony White

The Other One

Hi Anthony, my thoughts are that if you are heading for the world of management consultancy then go for brown. Why? Well knowing one or two as I do, it is a world (if you will forgive me) of the slightly enlarged ego! As long as your suiting is well and sharply cut, (not too NZ outback) then strut the dark brown stuff with pride. No doubt you will be working internationally, so keep some black for the more formal or conservative countries i.e. Italy, Dubai etc.

Welcome and good luck!



Really interesting post, and great blog. I am currently building up a collection myself, but my big issue is with finding a good fit – I am suffering some slightly poorly fitted Loakes at present. Where could one go in London that would have a decent range across different brands, and good service to help me find a good fit?
It seems like in most cases it is only the manufacturers’ shops that really help in finding the right last for your feet, and then only the more expensive ones (ie lodger etc).

Any thoughts?




The first pair of shoes are not Derby- it’s Oxford…


I can’t believe i haven’t read this blog before, it’s really good.

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Excellent blog, I’m looking for information on how to improve my health because I have some problems with my hair, so I would like to help me with advice on the subject, thanks!

Andrew A

I know this is an old post, but what is the 2nd shoe pictured there? I have not been able to find a pair of oxblood shoes that look so clean.

Andrew A

Good to know. Thanks!


Why should you store your shoes with shoe trees? My understanding was that shoe trees should be used immediately after the shoes are taken off so that they can cool down, contract and dry out around the shape of a tree – once the shoes have cooled off then you can remove the trees as they are no longer needed i.e. you only really need to own one pair of trees – am I mistaken?

Btw fantastic blog – I only found it yesterday and have already spent far too much time reading through old posts!


Hi Simon, i stumbled across your blog recently and have really enjoyed your reviews, especially the visits to different manafacturers.

Im trying to build a decent shoe collection (after spending many years wearing disposable cheap shoes from high street brands) but am finding it difficult to make a transition and find good shoes which are stylish, hardwearing and comfortable all in the same pair. I recently bought a pair of C&J handgrade collection shoes hoping to find all these qualities but dont find them comfortable although they look good and look like they will last longer than i probably will! Unfortunaltely they are giving me knee pain as the leather sole is so inflexible and v stiff! The sole is about 7mm, and made of oak bark tanned leather. Is it normal to find it such a tramatic experience when first wearing english leather soled shoes? I have heard english shoes are ‘solid’ but im finding them a bit too solid for my legs! Should I perservere with them in the hope they get easier with wear (i had after my last painful walk thought about binning them despite the price tag 🙁 )

From reading around I always got the feeling that C&J was highly respected (although not in the same league as Edward Green whose factory you visited in one of your blogs). Advice would be very much appreciated as im frustrated with my purchase!



Thanks for your reply Simon. No, I didnt wear them in slowly im afraid, as I wore them to and from the office it was became more like 9-10 hours at a stretch. The fit is perfect and the last works for my foot shape (358 last), I made sure of fitting issues by trying them on twice before buying.

I think on looking back that it might be a sports injury (as im a keen runner) that has flared up with wearing new leather soled shoes for long periods of time (and foolishly running a couple of times in them to catch a train when brand new).



Lodger don’t seem to make the first one anymore (in that colour anyway). Can you recommend an alternative in the same price range?


Hi Simon

I like to think that I’m a classic dresser but increasingly I’m getting the sense that I’m a conservative one!

For example, I work in financial services and in all my years haven’t dared to deviate from black shoes for work. But I’ve read you extolling the sartorial virtues of brown shoes so often that I decided it was time to take the plunge.

I was considering these oxfords from C&J http://www.crockettandjones.com/product/lonsdale-darkbrown which I don’t think are too dissimilar to what your friend purchased in 2009.

Do you think they are suitably versatile? It would be great if I could wear them with navy/grey suits at work and jeans/navy chinos/grey flannels more casually but I I wonder if I am describing some mythical shoe that spans the formality spectrum.

I know you said above that the shoes pictured were very versatile but I wonder if these C&J’s are too smart?

Thanks as always for your time and help and please know that I found this old post easily thanks to the new layout and structure of the website.


I can live with that.

Thanks for replying so quickly!


Building a shoe collection is indeed a great pleasure. The real pleasure however, comes from the knowledge that one has footwear for each and every occasion, having all the basics of formality and colour covered, and the confidence derived from that.

I can vouch personally for the Northamptonshire-based shoe manufacturers being a wearer of Loake, Grenson, Barker and Cheaney. The difference between these makers and high-end makers is just remarkable but the difference between these makers and low-end shoes is astonishing which is why I believe that Northampton-made, Goodyear welted shoes are the best value shoes in the World.


It would be great if you could advice.
My office is dress code leans more towards smart casual and so most of the time it is a nice shirt paired with tailored trousers and a nice shoes and belt, but unfortunately no jacket. I have a dark brown leather loafer and a dark brown suede loafer with me. I am looking to expand my shoe collection and confused whether to buy a black loafer or a dark brown Derby shoes.
1) Do Derby shoes look good without a jacket?
2) What should be my third choice of shoe as I already have a couple of loafers with me?


I am skeptical about black loafers. I think a burgundy loafer could be versatile.
If the choice is a loafer then what should be the next colour in line of not black?