The tips on looking good in a pair of shoes are simpler, in a way, than those for suits. They come down to two things: spend as much money as you can afford, because you are buying value and longevity; and look after them well, because you will be rewarded in style and longevity.

1. Don’t wear them everyday

Leather soaks up water from your feet. It dries and recovers naturally but needs time to do so. If you wear shoes for two days running the leather doesn’t have time to dry and wears down much faster as a result. Think about how wet cardboard frays.

2. Use shoe trees

The second-most important rule. Using shoe trees means that when the shoes dry they return to their natural shape, and don’t fold and buckle. In the long run, not using them will make the upper crack, which is one thing no one can repair. In the short run the shoes will look better and smarter.

3. Brush, cream, polish

Brushing down your shoes at the end of every day removes minor scuffs. They look better for longer and have to be polished less often. Cream should be used every month or so, depending on wear, and will keep the leather supple – aiding comfort and preventing the cracking mentioned earlier. Polish protects the leather and gives it shine; over time, it will lead to a beautiful, personal patina (less so on black shoes).

You don’t have to follow a dedicated regimen. But doing some part of this is well worth the effort.

4. Buy dark brown

Most men need black shoes for business – at least part of the time they spend doing business. For much of the rest of the time, they can wear dark brown. It is more versatile, going from a mid-grey suit to grey flannels to indigo jeans. It builds up a nice patina (try black polish occasionally). And it looks just as smart, if not as formal.

But always bear in mind that shoes should generally be darker than the trousers they are worn with. Tan shoes look cheap with dark suits – the contrast is too great. Dark brown looks best with navy and mid-grey (particularly flannel).

5. Spend money

I would estimate that men spend about a quarter of the amount they spend on suits, on shoes. It should be more like half.

Men that buy high-end shoes delight in dividing the number of days they wear their shoes by the cost, and compare it to a cheaper pair. This isn’t just a way to justify buying more expensive shoes. When shoes last 20 years or more, the calculation inevitably comes out in favour of better shoes. And that’s without taking into account how they look.

I got some criticism for saying in my last post that Edward Green shoes are better quality than Barker. Strangely, no one actually disputed that point. Barker shoes are made very well and are definitely worth the money spent on them. But even the Handgrade line that costs £400 or so is not as good as EG in my personal experience, and the majority are not Handgrade.

Too many men in this country wear terrible, glued shoes (sole not sewn on) with no toe puff (creating a soft, turned-up toe) in corrected grain leather. I applaud them buying Barker instead of that. But if they are buying a £3000 bespoke suit, they should be spending more on their shoes. With most English-made shoes, you get what you pay for. Spending more means better leather and more benchmade stages.

A friend of mine told me recently that his policy is to “buy a cheap pair of black shoes every six months and just throw the old pair away”. If by writing this blog I can stop just one person doing that, I’ll be happy.

[Pictured: bespoke Gaziano & Girling balmorals in espresso calf and crocodile]
Notify of

Inline Feedbacks
View all comments

Simon: this is fantastically useful information. But for those of us who are just moving on from the replaceable cheap pairs – can you give some basic advice on brands/styles/etc? Aside from the laces/non-laces divide, I’m afraid I don’t know where to start with shoes….as I suspect is the case for many men, footwear has always been a bit of an afterthought for me.



What about Crockett & Jones? How do they “rank” in your opinion? I have four pairs so far (all benchgrade, the 348 last. The handgrade lasts unfortunately do not fit my feet as well) and I love them, and think they not only offer great value for money, but probably some of the best value for money around (if one considers fit, quality of leather and durability).

Why should I spend twice as much on a pair of EGs? (I haven’t owned any EGs yet, so please enlighten me if there is something I am missing 🙂


Robin Parduez

I couldn’t agree more regarding point #4. Dark brown shoes are far more versatile than many of the tan shoes commonly sold on in high street shops. I also agree it can completely spoil an otherwise good dark suit if the tan contrasts to much with the suit material.


Simon. Very helpful. I would go as far to say that if you spend £3K on a bespoke suit, get a pair of bespoke shoes to wear with it. In my opinion the suit is still only part of the ensemble. The ensemble is still only as good as the weakest part.

I wear bespoke suits. For work (law in teh City of London) my handgrade C&J’s are sufficient. For an occasion, the same suit is significantly lifted by a pair of MTO G&G shoes… likewise the same suit – paired with bespoke shoes – is just top line… noticably so. The shape and colour of a good pair of bespoke shoes can be aproached but not achieved by a pair of MTO shoes.

As to colour, I would add to dark brown, dark red, ie ox blood. I think the latter is more beautiful (than dark brown) with mid grey and blue suits, but is less versatile (when in the context of an ensemble) than dark brown. J


Nice article Simon. I agree totally with S. I’ve got a couple of pairs of Cheaney shoes and I find the quality and fit great. I understand the company’s improved a lot since being bought out of the Churchs-Prada stable. There’s no doubt that EGs and G&G look beautiful, but the huge cost seems hard to justify…



I’ve noticed that a lot of clothing aficionadoes eventually become shoe fetishists (in the nicest possible way). I’m not really convinced though that people have to be spending a lot of money on many pairs of shoes, especially if they are not made of money and only trying to dress as stylishly as they can sanely afford.

Tips in that direction would talk about the best for one’s money, because it IS possible to get well-made shoes with sewn soles that aren’t passing the £300 mark.

A lot is said about how a £500 to £1000 pair of bespoke shoes actually pays for itself over time, which has a part-truth to it only. The cost of resoling and occasional professional maintenance is rarely factored in. And the fact that quite a few pairs are needed for rotation puts shoe cost into the thousands and makes people feel like they are dressing poorly in their inability to manage it.

Good clothing does cost a bit more, but discussing ‘top-end’ all the time shuts out everyone but the moneyed set.

The Shoe Snob

Simon, great post! Hope that all is well. See you around



Someone asked for shoes at the £300 mark: C&J Handgrades in the sale are hard to beat. Edward Green sale if you have a bit more to speand. These shoes will be seconds, but are only slightly so… ofentimes one can hardly notice the difference. J


Well said Roger,

I reckon that only a small proportion of the readership of this excellent blog (and it IS excellent!) could afford to drop a couple of thousand pounds for 2 or 3 pairs of shoes?


Bespoke shoes for £500-£1,000? Tell me where.
The Boot Bro.


Simon, I rotate four pairs of shoes for work and as a result they all need a full resole every year. Barkers (ha ha) will only do this twice so their shoes need to be replaced after the third year (I’ve yet to find out C&J’s policy on repairs). Does an improvement in quality significantly affect this equation or are quoted lifetimes of 20 years in fact based on having many more pairs of shoes? For many, I imagine, not only is the cost difficult to cope with but where does one store all these shoes?


I do not think C&J have a limit on the amount of time sthey resole… I have a pair of Hangrades from 2006 that have been resoled at least three times… there is nothing wrong with the upper and they just keep going. J

Reto Zimmermann

Great post. These basic points for shoe-maintenance cannot be repeated often enough!

I’m somewhat surprised by the commentators who find it necessary to resole their shoes every year. I wear shoes with leather soles most of the time for work and on the streets in Europe or Seoul (which is somewhat rougher terrain sometimes) and go many years on a pair of shoes before a resoling becomes necessary. The only exception is that some of the shoes with softer soles had to have a toe-tip repair fairly quickly.

As far as justifying the price for more expensive shoes is concerned, there is no one reason in my experience.

Part of the added price buys better quality materials, not just in the upper leathers used, but importantly also in the soles.

Another part buys added craftsmanship, nicer work in the details, and let’s be honest: aren’t the details what make the difference when it comes to refinement?

Last but not least, the extra money goes into exclusivity. Owning a pair of Gaziano & Girling is more of a luxury than owning a pair of Crockett & Jones not just because of the money one has paid for them, but because C&J has a much, much larger production, which is able to operate at lower costs than a smaller manufacture. However, this makes their shoes also less special, and I’m saying this as someone who generally likes C&J very much, too!

Finally: Hi Justin! Small world! 🙂


Simon, hello from Sydney. I really enjoy your writing. I have to disagree however with your view that tan shoes are wrong with darker blues and greys. I actually agreed with you until I spent time in Milan. Please don’t try to tell me that all those stylish Milanese guys are wrong! I think it’s an English v. Italian thing… personally I’ll take Italian every time.



I have just had the most crushing visit to my local Church’s store, where I was informed that if I had them send my shoes to their factory, it is very likely that they would be thrown in the bin and not returned to me. The reason for this is that I’ve had them resoled about 4 times. This has always been done by Church’s themselves (with the additional cost, the incredibly long wait (up to 10 weeks) for their return, and the general annoyance). I have always broken in new soles in the dry, I wear the shoes 1-2 times per week, polish them regularly, dry them out properly, use shoe trees and a shoe horn, etc. I thought the idea of Church’s was for them to last for ever with their amazing repair service? This pair is less than three years old, I’ve done everything right, and now they’re telling me they can’t resole them (nothing else is wrong with them). Disgraceful – from now on my local cobbler (2 day turnaround) will be seeing this business, and I’m switching from Church’s to something else.

Andy Liu

Hi Simon:
Hope you are well. I just got back from ED outlet sale, bought a pair of tan shoes with matching belts. How do i pair with trousers? i think it will go well with cream or stone colour, any other tips? Does it go well with Raw denim as well?

Thanks vm



Hi. Recently, I’ve been researching on the different brands of high-end shoes when I happen to come across your very informative blog. It’s just that I don’t know a lot about leather shoes, and as i’ve been reading your blog, i’ve been more inclined to ask your your opinion in this particular matter. I would like to ask which brands you prefer in the category raging from 1000 above but obviously not bespoke level. My preference seems to be leaning towards the classic cap-toe, with a shade of brown. Hope you can help!

Kristian Devoy

How do you rate oliver sweeney I have a couple of pairs and find them very comfortable ? . I must confess having had Barkers , Cheaneys and oliver sweeney that Cheaneys would be my favorite . Barkers sadly seem in some styles sadly to use cemented construction which in my humble opinion reduces their quality .


@Kristian – Oliver Sweeney shoes were a favourite of mine a few years back when I started to upgrade from (shamed to admit) shoes that would last six months.
I’m still a fan and continue to rotate them in – you’re right that they are incredibly comfortable.
I bought a pair of Barkers once from a City shop’s “closing down sale” and they lasted about two months – no doubt was a cheap construction (I paid well under £100). The upper was completely destroyed by road salt one day too!

David Dunville

Loakes make wonderfull top quality shoes I have 4 pairs and love them highly recommended

David Hudson

I have a pair of Loake Aldwych and Buckingham from their 1880 collection and have found them to be of a quality way above their price bracket. I picked them up on line from where they included some nice trees.

Frank Osei Owusu

Simple and nice, to me is the best…


Hi Simon,
Do you know the difference between polish and cream? Which one should one use and how often?


Simon, how do you keep your shoes clean throughout the day? Do you carry a small brush with you and clean them occasionally?


On a rainy day you don’t brush off the dirt that invariably builds up on shoes as soon as you walk outside?


Simon, a question on shoe care: what are your views on protecting the heels and soles with rubber/vibram outsoles, and or metal toe-tips, to make them last longer. Please keep in mind that I don’t usually have the option of sending the shoes to the maker for resoling. I also walk a lot and am afraid my nice shoes will wear out too fast. Thanks!


Thanks, Simon, good to hear. Many bloggers are against but I don’t see the disadvantage, esp. in my case. Also good tip for the nails, thanks. And if from you’ve heard good work on resoling can be done by a 3rd party all the better, helps me consider that option too! Thanks!


I bought an expensive pair of shoes and it lasted me for almost twenty years. Its time to invest in another pair of good quality shoes.

I love Barker shoes, but I was checking the reviews on Trust Pilot, the reviews were not very good. I like the Crockett and Jones shoes as well but they are more expensive than Barkers. I will hang on for now.


Hi, Simon! Could you please recommend a good pair of shoe trees? Where would you purchase them online?
– H



Do shoe trees need to be purchased from the shoe manufacturer? Can I switch shoe trees between manufacturers in my shoe “wardrobe”?

Also, same trees for a pair of unlined suede shoes versus lined leather or Corsican oxfords?

Thank you.


In your opinion, can oxfords ever be worn casually? Say a shoe like the Allen Edmonds strand in a less formal color like walnut. If you were to build a casual outfit around that shoe, what would you wear?