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JM Weston Triple Sole Brogue - Hard to Break In!!!JM Weston Triple Sole Brogue – Hard to Break In!!!

When you think about buying shoes, most people probably think about getting the most comfortable thing that they can find, as when we are not sleeping, we are most likely on our feet. Now assuming that our feet were made for walking on earth (dirt, soil etc.), one would think that wearing stiff leather in comparison might not be the most sound idea, which is why rubber soled shoes can be so popular. But as leather has been found to be the best resource for a pair of well made, built to last dress shoes, it is something that we are stuck with using. However, the idea of stiff leather leaves many people around the world quite fearful of certain shoes, particularly goodyear welted ones, as they tend to be among the stiffest in ready to wear shoes (at least in the beginning). Because of this, many people don’t know what to expect and therefore may deter from actually buying these shoes. Due to this, and the fact that I love to break stereotypes (in the footwear industry especially), I have decided to give you my thoughts on what to expect for the first 30 days of wearing your new shoes.

Glued/Cemented Soles

On a glued sole shoe, there should really be no break in period. Most of the time, you find that rubber soles are used anyway on a shoe that has a glued sole, so the pairing between rubber sole and most likely a relatively soft leather (think the majority of Ferragamo’s loafers – as shown above) leaves for a virtually pain free experience. The shoe should feel good right away, and if it doesn’t, then don’t buy it. What they tend to lack however, is true support which for me is what gives real comfort.

Blake-Stitched Soles

Magnanni Shoes, Blake-stitchedMagnanni Shoes, Blake-stitched


Whether or not your blake stitched shoes will have a break in period will greatly depend on several factors. First and foremost, thickness of the sole. Take Santoni’s Fatte A Mano range for example, which are all blake stitched. Some of them use very high quality leather that is quite substantial and therefore quite stiff. In the beginning you can expect there to be a bit of stiffness and possibly discomfort (in the sense that it won’t feel as flexible as your glued sole counterparts), but being that blake stitched construction is not intended to be overly rigid, this stiffness should not last long. Within one week, this stiffness should go away and in some extreme cases may last two weeks.
On a blake stitched shoe with a very thin sole (think Italian summer loafer in suede), there should be virtually no break in period with the sole, but what you might find is that depending on the upper leather, there might be some period of softening up of the upper. As most of the blake stitched shoes with a thin sole tend to use a thin and flexible upper leather, this break in period should be within a day or two of wear. There are always exceptions to the rule but as a generalization, blake-stitched shoes should not ever take more than two weeks to become soft and flexible.

Goodyear Welted Soles

Alden – Picture Courtesy Of: Leather Soul
This is the construction that many people who are not familiar with, will struggle for their first time of experiencing it. Due to the nature of the construction, where there are multiple parts of leather stitched to each other in order to create a very strong and durable bond, the shoe will virtually always be stiff in the beginning and thus might cause discomfort for those not used to it. Therefore, allow me to break down the first 4 weeks of using them for those that have never tried a goodyear welted shoe before. This example is for the extreme cases as in reality they are not so bad, especially when used to them.

Week 1

Plain and simple: If you are not used to it, the shoe will feel incredibly stiff. Now, depending on the upper leather used, this stage can be quite unbearable for those that have never suffered through it before. You might find yourself with blisters on your heels, leather cutting into your toes, sore arches, or just flat out not enough cushion in your insole. All of these discomforts should go away, so don’t worry.
In some cases, depending on how you like your shoes to fit, the shoe might feel slightly too small due to its stiffness. However, a shoe’s leather will always stretch, but that is not to say that you should buy a shoe that feels uncomfortably tight, but more so if it is ‘snug’ then not to worry as from snug to normal, just involves a bit of wear and softening of the leather. Once ‘snug’ has broken it, it should become ‘just right.’

Week 2

Depending on the upper leather used, and the thickness of the sole, the shoe might still be stiff. But if it is, it should be significantly less. The heel counter should be considerably softer by now, not giving you more blisters, but maybe making the previous ones still hard to heal. If you have a cap toe, the toe stiffener might still be cutting into your toes as these sometimes take a while to break in. The sole should be a lot softer now, so your arches should start feeling like they are molding to the insole, and therefore should not feel sore by any means.
Goodyear welted shoes with a flex sole by J.FitzPatrick FootwearGoodyear welted shoes with a flex sole by J.FitzPatrick Footwear

Week 3

While the shoe won’t be completely broken in quite yet, it should start feeling a lot more like a normal soft shoe. All of the aches and pains should not occur anymore, and if they do, then something is not quite right. At this point, home remedies in softening the leather up should be considered (I will explain these below).

Week 4

The shoe should feel good now, through & through. The insole should be molded to your foot, almost as if you have a custom arch-bed inside. The leather everywhere should be considerably softer, but it will never feel like suede, so do not expect that. You should not have any discomfort anymore. Now, the one exception is if you are wearing cordovan leather shoes. While I have never owned a pair myself, I do know that their break-in times are significantly longer, some people even saying that they never really soften up completely.

 Manually Softening The Leather
Breaking in the heel counter can be done two different ways. The first way involves putting the shoe in front of you (toe facing away) and with your palm, bending the top of the heel leather downwards into the inside of the shoe (similar to shown above, bending down whatever spot is bothering you). While this will cause a bit of creasing in the leather, it is the surest way to soften up the heel stiffener that is between the liner and upper leather. Give it a good 4-5 pushes and hold down 2-3 seconds for each push. The second way is to take the convex side of a spoon, and rub back and forth on the upper bit of the inside heel counter. Rub thoroughly (for at least 10 hard strokes), but be careful not to fray the stitching.
Softening up the toe piece and/or upper leather at forefoot joints, involves a rounded broom handle (or any object long enough to get inside of the shoe, that is stiff and has a round end). You will want to stick the broom inside of the shoe, where the leather is stiff, and rub intensely using the hand holding the shoe to guide where the end rubs on the inside. I hope that this makes sense.
Paolo Scafora's handwelted shoes use a special technique that allows you to bend the shoe in half
Paolo Scafora’s welted shoes use a special technique that allows you to bend the shoe in half
Now if doing all of these things still does not do the trick or that your arches still aren’t feeling quite right, then more likely than not, you bought the wrong size. The shoe will most likely be too big and the friction from not having a taut hold will be causing heel blisters and will make your breakpoint (where the shoe creases in the forefoot) sit in the wrong area, causing it to dig into your toes.

This post is a general guide to stiff goodyear welted shoes as well as blake stitched shoes with thick leather uppers and soles (i.e. blake-rapid shoes). Not all shoes will break in the same way. Some will be significantly less troublesome to break in (such as my Gaziano & Girling balmoral boots were) and others might never really fully break-in (think cheap cordovan or shiny bookbinder leather (also cheap)). It will vary shoe upon shoe, maker upon maker and leather used for each model. But just because a shoe is stiff doesn’t mean that it should be ruled as uncomfortable. Some of my most comfortable shoes started off really stiff, but once broken in, feel more supportive and comfortable than my softest shoes. Everything will vary, but allow this to give you a general idea of what to expect!


Handwelted, bespoke Gaziano & Girling shoes
Hand Welted, bespoke Gaziano & Girling shoes

38 thoughts on “Breaking In Shoes – Your First 30 Days”

  1. What I’m wondering, Justin, is how often/long you’re wearing the shoes in these weeks. I guess if you’re “rotating” them once or twice a week this makes sense. Otherwise I’d say if you wore them a lot, normally a few days is enough to get them feeling like they’re yours.

  2. Good question Alex, I was wondering the same thing. I wear my EG Malverns about 2X a month. I’ve owned them a year now, do you think they’ve even been broken in?

    1. Let me also add to what Alex mentioned. Because I’ve worn alot of military leather boots and I’ve worked in the shoe repair industry, a good way to speed up the breaking in process is to wear the new shoes around the house for a couple hours at a time each day. Should be equivalent to the time you spend on your feet at the office. Most of the time my shoes have been broken in before Ive worn them out for the first time. It’s always worked for me.

  3. By the way, thanks for the tip on the sale! Just so happens I have to hang around in London for a few hours Friday afternoon…I think I know where I’m going now!

  4. Alex B – Yes you are right…only that the stiffer the shoe (and the more the person is not used to this feeling) the more likely that the person will wear them only a few times a week, as they won’t be able to bare the brute of a hard and fast break in

    Derrick – EG’s leather is quite soft, so I guess that they have been alright? The sole is probably still stiff though as 2x a month is quite little…

    Alex B – ah you should come say hi Alex!


  5. found this post now, better late than never, but when you talk about breaking in a shoe, like in the first week how long should u wear the shoe for? like wearing it inside with minimal walking around or walking for like 20+min than wearing them all day.
    What would be a good timeframe to break in a stiff pair of goodyears

  6. Avi – breaking in a shoe needs to be done by wearing it normally, throughout the day…one cannot break in a shoe at home as you simply don’t do enough natural movement and walking at your house as you would in the street. Timeframe can be anywhere from a few hours to 2 weeks, it really just depends on the shoe and the wearer….


  7. Hi Justin, I’m a woman who purchased a pair of leather flats online. They arrived today and I’m not sure now whether I should return them or try to break them in. The reason is because the toe box feels too tight. My toes have enough room in the tip, but side-to-side it’s tight.
    This article was pretty helpful on the process of breaking in men’s leather shoes…but will it be worth it to break my flats in, or are they just too small?


    1. if a shoe is snug in the beginning then most likely it will break in to become just right…if a shoe is simply outright tight (uncomfortably), well then I must say that the chances of them getting to the point in which they are comfortable is unlikely….hope that this helps

  8. Justin, have you a view as to how best prolong the life of leather soles.
    I appreciate impact of wearing in the wet etc, but is there an oil or product which can be applied which would help extend their use.

  9. This is the one area about buying expensive shoes I hate. You get the not inconsiderable amount of money together and with much excitement hurry on down to your favorite shoe shop or manufacturers shop of your choice only for the whole process to become somewhat of a nightmare. What we really want iffor the salesman to tell you, “these shoes are a perfect fit for your feet”, however this never happens as most of us do not have perfect feet or indeed very often one foot is slightly smaller/bigger than the other. The salesman can only be so helpful as really the final decision is up to ourselves. Even after we persevere and end up at home with our purchase the doubts begin, are they too tight/loose, too narrow or too wide, too long or too short ect, ect and none of this will really become apparent until after the break in period. What exactly does a snug fit mean, does it mean slightly tight or just a good fit. If a shoe salesman cannot explain this how do I decide as a layman. I know I exaggerate a tad but is the day where we can place our feet into a 3d machine that will link our size with our perfect fit that far away.
    One other consideration is the manufacturer and type of shoe. For instance a pair of Alden calf can seem much stiffer than a pair of C&J handgrades in calf so does the breakin period differ and because the leather in the Alden is stiffer should we go for a tighter fit in the Alden when buying the shoe. How people buy shoes like these online is beyond me unless of course that already have a pair and know their size.

    1. dear Tony,

      fit is subjective so you as the purchaser need to decide whether or not something feels good and fits well…a shoe should feel hugging at first and then perfect (as one can be) once broken in…. 3-D machines don’t work (and people have already tried) because it gives you theoretically a “perfect” measurement for fit, but it does not take into account personal preference i.e. many Americans and English like loose fitting shoes while many Europeans like a very snug (and sometimes overly) fit….therefore this idea is unfortunately null…. Shoe fitting is just one of those things that will forever be difficult for some and easy for others, but not because of the shoes, more so because of the person trying them….

  10. I bought a beautiful pair of Donald Pliner brady chukka boots. They were very stiff when I got them yesterday. I put some mink oil on them and overnight they have losened up. My only issue is I think I would have liked to keep them stiff and their contour exact. Did I screw up by putting the mink oil on and potential over softening and early stretching or did I do the right think by protecting the boot and also softening so that creases won’t be so drastic and my feet feel more comfortable than tight…. I almost want to return them and get another pair so that stiffness lasts and will wear naturally…..

    Please respond in driving myself insane.

    Justin L

    1. you did not do anything wrong at all so don’t worry about that….better if anything as the mink oil would help the creases to not become too prominent too quickly…

  11. So if i bought a goodyear welt shoe and it feels normal right out the box, does that mean I got the wrong size?

    1. there is no right or wrong answer here as fit is ultimately subjective…your “normal right out of the box” might be different to mine, so I can’t judge what that means…I think that a shoe should be snug in the beginning so that when it breaks it, it fits perfect later

      1. I always try to get the right fit so that the creases on my new shoes match and look symmetrical. The Achilles Shield insole has been a lifesaver. I only remember to put them in after the first day in a new pair of stiff shoes, but once I do they let me break-in new shoes to the shape of my foot without the bloody cuts at the back of my heel from the shoe digging in. got them at Saw on Amazon too

  12. pauletterollins

    i normally wear size 11, but actual siZe is 10.5. When i buy leather sole shoe, fear is they will stretch and be loose on feet if buying 11. Cause for concern. Spoken by a woman

  13. Hi, I was wondering if you polish your shoes before breaking them in or is it best to wait until after?

  14. Hi, I bought a couple of Crockett & Jones a while back that have been sitting unused for quite some time, because I chose the wrong size. Even after the breaking-in period, they are just too tight, as my toes feel too constrained. Is there any solution to this? Maybe with a last? I would hate to have to give them away… Many thanks your blog is great. Jacobo.

  15. Nice advice. I have a new pair of Memphisto Paolino wingtip oxfords and the left heel is riding my ankle quite hard initially – so much so that I had to stop wearing them. I will give these tips a shot to see if it will help remedy it

  16. Matthew Schachter

    very poor advice. shoes should ALWAYS fit comfortable from the get go, blisters and pain should NEVER be the norm to any shoe, goodyear or not! If its painful and giving you blisters, regardless of construction, its the wrong size for you. Too many men buy shoes that are too small for them. Always accomodate the larger foot, and shoes must be comfortable from the beginning. I have no idea where this “leather stretches” myth comes from – there is a FINITE amount of leather there, it will get softer sure but wont get any longer in size. That is total bs.

    1. Very poor comment. Try buying a pair of redwing shoes and tell me you should have comfortable shoes from the get go. Tough leather needs breaking in and it CAN involve blisters/discomfort the first few weeks. If you meant after a few weeks you still have blisters then I agree and apologise.

    2. I’m no expert in leather, but I imagine a lot of the “stretching” effect is actually the leather softening and conforming more to the shape of the foot, fitting closer to the skin, which will allow it to stretch further around the foot (particularly at the lacing point), rather than an elasticity in the material.

  17. Hi,
    I was gifted a pair of new Church’s Graftons(an $850 shoe) over two years ago. I had the store fit me in what they assured me was the right size. I was ready to deal with a long break in period.
    6 months later after regular wear, they still hurt the tops of my feet, my insoles and my back after lengthier walks. I visited the store, and all assured me it was the right size.
    Cut to today, two plus years later…
    They’re still stiff, hurt my feet, are tight up top, but loose in the heel unless I have thicker socks, and overall a bit crippling, while, yes, admittedly getting occasional complements on how nice they look.
    Church’s Headquarters wasn’t much help, and today I took them back to the store for the second time. The salesman again assured me nothing was structurally wrong with them. It could be my feet… I left them with him so he can stretch them out a bit to see if that might help.
    Naturally no one wants to take the blame for anything.
    Does anybody on here have any advice, similar stories, or any general thoughts about this ongoing frustration?

    Thanks! Jason

  18. spack mc spack

    I never had this type of problem. I own various goodyear-welted shoes of different brands (mainly Barker though) and all of them felt incredibly comfortable from the beginning and just got even more comfortable after wearing them for a couple of times. When it comes to dress shoes I would never ever go back again to those cheap glued ones. Looking back those were the one that gave me sores and blisters breaking them in. Thing is, you need to know your size and whats probably even more important, the width you are going to need. If you buy the correct size you shouldn’t have any problems from the beginning.

  19. My advise is to take with you a pair of thick woollen socks when going to buy a new pair of leather shoes. Trying on with these socks the thightness around your feet is just right to guarantee perfect fit after short break in period. Also remember to wear your loafers with woollen socks for first couple of days at home.

  20. Hi Justin, I know that this is an old post but hopefully you’re still checking in on replies. I’ve a few pairs of good shoes, including some C&J and a pair of your own fine shoes. Over lockdown, I worked from home and most of the time was in slippers, bare feet or – when out – retired running shoes*. I think my feet have become ‘soft’ as a result. Now, when I get the chance to go into the office, I like to pull out my good shoes. The problem is, I’m seeing a lot of blistering and discomfort that I wasn’t getting quite so much before.

    My question is partly for tips on toughening up the heel area, but also on how to know when the cause of heel discomfort and blistering is due to the fit being too tight, or too loose, or simply just not broken-in enough.

    The worst culprits are my C&J Islays, which C&J suggested I sized down a half size from what I would wear in their 348 last. They seem to have just enough room but there is movement in the heel and I can end up with serious blistering after only a couple of miles of walking. How would I determine the cause of this (i.e. too big, too small, not broken in)? And is it worth considering heel grips ever?

    Thanks in advance! John.

    * I run, but retire my Mizuno Waves after about 500 miles of running; they then see another 300-500 miles of use for walking duties, then they are usually totally done-in 🙂

    1. Justin FitzPatrick

      Hey John, sorry for the late reply here. Heel grips should help, at least they will add cushion where you are presumably getting your blisters. Alternatively, when I need to really break in a shoe and know that I am going to get heel pain, I will preemptively add thicker bandaids in the culprit area until the leather is broken in. I hope that this helps

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