How Long Does Formal/Smart-Casual Leather Dress Shoes Take to Break In

You got a new good looking pair of leather dress shoes. 

For the first few wears, it is uncomfortable and gives you blisters. 

But somehow after a period of time, it magically becomes more comfortable. 

This is called the break in period. 

Let me explain more about this magical break in period. 

Why Does New Leather Shoes Feel uncomfortable

You can tell these shoes are stiff just by looking at it. 

You can tell these shoes are stiff just by looking at it. 

Dress shoes tend to be stiff to look dressier. Leather is stiff when it is new.

It is unlikely for leather to be "soft" when it is new. 

Especially for quality leather dress shoes. 

Stiff leather is uncomfortable because it is not flexible

This would give rise to the discomfort

As the stiff leather cuts into your feet or give blisters

Over time, the upper leather would mold to your feet and soften.

Your feet would make an impression on the leather sole, giving a more customized fit. 

Then your shoes are now broken in and comfortable. 

Factors That Determine the Break In Period


  1. Shoe Construction
  2. Upper Leather
  3. Material and thickness of sole

I will explain the break in process behind the different construction and factors

And give an estimated break in period in for the various construction

Rubber Soles/Cemented Shoes

Cemented shoes should have relatively no break in period. 

This is because they are likely to use a rubber sole. 

Rubber sole is more flexible and less stiff than leather

And with the cemented/glued construction not providing as much support, 

This means the shoes are not "resisting" your feet and should be comfortable right from the start. 

If it is not, don't buy it. 

However, cemented/rubber sole shoes lack true support which is what gives real comfort over time. 

Furthermore, the soles do not mold to your feet so the fit does not get better over time. 

Break in Period: Less than a week

Blake-Stitched Leather Shoes

Blake leather shoes are made with lightness and flexibility.

Yet possess more durability and support than the cemented construction. 

Two factors affect the break in period for Blake shoes

1.) Upper Leather

Quality full grain leather can be stiff at times.

This gives the shoes it's shape and look. 

In the beginning, there will be stiffness and possibly discomfort (likely for quality leather) 

But as Blake shoes are not overly rigid,

it should last about one to two weeks. 

2.) Thickness of Leather Sole

The thicker the leather sole, the stiffer it is. 

The stiffer it is, the more uncomfortable in the beginning. 

However, the thicker the leather soles, the more durable the shoes are. 

This becomes a trade off in comfort and durability. 

leather soles will always be stiffer than rubber soles. 

But it molds to your feet over time, providing a more customized fit 

And it provides more support. 

This increases the break in period. 

Overall Break in Period: 2 weeks


Goodyear Welted

This is the construction that most men are not familiar with. 

The nature of this construction are that it will always be incredibly stiff in the beginning. 

Goodyear welted shoes are

  • heavier and
  • less flexible than Blake and cemented shoes. 

This is because of the welting and the synthetic bonds used. 

Breaking into goodyear welted shoes require time and patience. 

So if this is your first time, it may get a little getting used to. 

I would advise having another pair to rotate to rest your feet. 

The first week might be slightly unbearable for people who are not used to this.

Blisters, sore arches or leather cutting into toes are normal.

It is not the brand or quality that is poor or anything. 

However, once you get past the 4 weeks period, you should not feel uncomfortable anymore. 

Break in period: 4 to 6 weeks

Like Blake shoes, this is dependent on the thickness of your soles and stiff of your upper leather


Remedies To Break In Your Shoes


I would recommend these remedies for goodyear welted shoes. 

As cemented or blake stitched shoes should break in relatively quick 

So just wearing them out should be good enough. 

Two main areas that is exceptionally stiff in shoes, 

  • The toe
  • the heel counter area

1.) The heel counter

Not dress shoes, but you get the point.

Not dress shoes, but you get the point.

  • Put the shoe in front of you (toe facing away) 
  • Bend the top of the heel leather downwards into the inside of the shoe
  • Give it a good 4-5 pushes
  • hold down 2-3 seconds for each push.

While this will cause a bit of creasing in the leather,

it is the surest way to soften up the heel stiffener

2.) The toe area

I would suggest bringing it to a cobbler to expand the width. 

Make sure to tell him which areas are painful

He would apply a leather softening cream and expand your shoes accordingly.

Estimated cost would be from $15 to 30. 

Alternatively, you can apply the softening cream yourself

And use a bigger shoe tree to stretch the shoes.  


Blaked stitched CustomMade shoes

Blaked stitched CustomMade shoes

I've tried cemented, blake stitched and goodyear welted shoes

Personally, cemented shoes lack the support and durability that i would like. 

And goodyear welted shoes for me is just too stiff and heavy.

Personally, breaking into them feels too much of a hassle and pain. 

That being said, goodyear welted shoes are very durable and they can last a long time.

To some, that one month of pain is worth it. 

My CustomMade shoes are blake-stitched. 

One of the reasons i decided to use the blake construction is because of the lightness and flexibility

Yet it possesses durability and support. 

This means minimal break in period. It is a balanced construction. 

If you're just a regular dude who just want a good looking and good fitting shoe

I would recommend Blake construction. 


Key Takeaway: All leather shoes need a break in period.

The length of the period depends on the upper leather, the soles and the construction of the shoe. 

CustomMade Opening Promotion

We are moving to a new showroom at 82 Telok Ayer St, #02-04. Our opening will be tentatively on 15th May!

Until then, we won't be able to accept appointments. Sadly.

We'll be offering a one time opening promotion. 

This would be available for those who sign up to our list and Like Our Facebook! 
(if you're already on the list,  you don't have to sign up again)

Your Shoe Guy

The interesting lowdown about leather dress shoes

3 Step Checklist To Find Your Perfect Dress Shoe Fit

Should My Belt Match My Shoes?, Answer By A Shoe Insider

4 Factors That Lead To Unsightly Creases & How To Remove Them

How Long Should My Dress Shoe Last? 

CustomMade Updates On New Showroom And Collection!

It's been a long and eventful year for CustomMade at Centennial Suite,

The serviced office that we leased for our operations.

It's a bittersweet moment as our lease ended on the 17th Apr,

Signaling the end of one full year.

I initially wanted to move to a serviced office,

As i wanted my room back and also the location would be a huge convenience. 

Lastly, the short lease and small space is perfect for CustomMade then.

My mum and I made the decision to move out because the space was too small.

We had no room to grow.

New Showroom

Retail .jpg

CustomMade will be moving to 82 Telok Ayer, #02-04.

It is a bare office space that is bigger.

Renovations are underway as we're going through a re-branding as well.

The estimated date of reopening would be 15th May.

Haha, yes, i know...that means we won't be in operations till then.

Partially my fault due to the lack of adequate planning and procrastination on the renovation plans.

Hey, i'm only human so i'm gonna go easy on myself.

On the plus side, that also means a month of no operations.

BREAK TIME! It's all about perspective!

My mum is no longer young and she lacks the vitality and energy like i do

So i figured it would be a good time for her to just unwind and relax. 

New Team Addition To CustomMade

There will be a new team member for CustomMade, Nigel, my younger brother.

Nigel will ORD this coming May and like most 20-somethings,

We are completely unsure of what we want to do.

Rather than studying in a course that he has no passion in,

I told him to join me in my pursuit of "real world" education

And building a sustainable organization.

As for CustomMade, we'll be spending this one month break to brainstorm the future.

Mainly, our mission and our vision and the strategy involved.


New Collection of Colors

There will be some big changes to CustomMade after our opening as well.

A brand new collection with new colors!

  1. Black
  2. Dark Brown
  3. Chestnut Brown
  4. Dark Tan & Dark Tan Burnished
  5. Oxblood
  6. Burdundy
  7. Navy Blue

We are improving on the looks and quality of our shoes.

Our shoes are now 100% hand painted and hand burnished

As we just got a new coloring expert!

That means each shoe is completely unique.

While there may be two shoe orders with the same color,

it will not be 100% identical.

Hand colored shoes will have a richer character in color and age!

Order Processing And Updates

We hear your feedback. 

We are working towards cutting the lead time and better tracking of production.

Tracking will now be relatively real time. 

We'll update you via email of which stage of production your shoes would be in.

We are working on this automation software. 

Hopefully, we should be able to launch this in line with the new opening.


The CustomMade Experience

More importantly, we will be implementing proper processes to the shopping experience here at CustomMade. 

  1. CustomMade designing process

    One to one personal guidance on which design and color is best for you
  2. CustomMade fitting process

    3 key steps to our fitting process - Measurement, Standing test, Walking Test

I would share more details as we go on! 

Change in Pricing For CustomMade

There will also be a change in pricing for our entry level CustomMade shoe.

Our new collection is a new and improved version of the old collection.

The customer experience will also be improved and value added. 

Our range will go from $330 to $360.

Rest assured that there will be an opening promotion.

And also, a special discount for existing customers for their support throughout the year! 

CustomMade Opening Promotion

We'll be offering a one time opening promotion. 

This would be available for those who sign up to our list and Like Our Facebook! 
(if you're already on the list,  you don't have to sign up again)

Check out CustomMade's Story

This is mainly my narcissistic rant of my personal journey to creating CustomMade

How I Went From Big 4 Auditing To CustomMade

How I Underestimated The Product And Failed The First Time

The Correct Way To Lace Your Leather Dress Shoes With Style


It is funny most men don't know how to properly lace their leather dress shoes.

Why get a quality good looking leather dress shoes if your laces look bad?

It just ruins the whole look.


types of shoe laces

There are only two types of shoe laces you should use for your leather dress shoes. 

  1. Round laces - more formal, use for oxfords
  2. Flat laces - less formal, use for brogues/derby

The length should be from 60 to 80 cm

Quality laces should be waxed

And made out of cotton

Do not use nylon extra flat/wide athletic laces for your dress shoes

Please feel free to experiment with the colors! 

if you want to play it safe,

Go for darker and more similar color to your shoes

2 main type of lacing for leather dress shoes

There are two main ways to lace your leather dress shoes.

  1. Straight  - formal for oxfords
  2. Criss Cross - informal for brogues/derby


Leather Dress Shoe Straight Lacing

Straight lacing is typically for oxfords or more formal shoes

Due to its straight edge look. Pun fully intended. 


  • Completely unlace your shoes. Ensure both laces are of equal length.
  • Begin straight across on the outside and in through the bottom holes.



  • Point the toe of the shoe towards you
  • insert both ends of the shoelace in the bottom holes (the eyelets closest to you)
  • Pull both ends to ensure that they are even.
  • After ensuring that that shoelaces ends are even, pull the laces taut.

    Now, you have your first bar.

On shoes with odd numbers of eyelet pairs,

Adjust so that the left end is slightly longer than the right end.



  • The left (blue) end runs straight up on the inside from the first eyelet to the second
  • Then straight across on the outside to create the second bar.


  • Run the right end (brown) of the lace along the underside of the eyelets
  • Bring it from the first eyelet to the third eyelet on the right side of the shoe.
  • Pass the left end of the shoelace from the second eyelet to the fourth, also on the right side of the shoe.
  • Both ends run straight up on the inside, each skipping one eyelet and emerging two eyelets higher up.


  • Both ends of the shoelace continue straight across on the outside and in through the adjacent eyelets.

Now, you have your third and fourth bars. 



  • Pass the right end of the lace (brown) from the third eyelet to the fifth.
  • The left end of the lace (blue) runs diagonally across from the fourth eyelt on the left side to the fifth eyelet on the right side.


  • To finish off the lacing, ensure that your shoelaces are of an even length.

    They may require a slight adjustment to ensure that the ends meet when the laces are pulled tight.
  • Now that you’re done, it’s time to tie your shoelaces together.

Straight Lacing Video Demonstration

Leather Dress Shoes Criss cross Lacing

Criss cross lacing tend to be less formal 

And is meant for brogues or derbys

The yellow means one side of the shoe laces

While the blue meant the other side. 

Image taken from The Art Of Manliness

Image taken from The Art Of Manliness


Key Takeaway: Use straight lacing for your oxfords

And criss cross lacing for your derbys/brogues

Use a round lace for your oxfords

And a flat lace for your brogues/derbys

When in doubt, just go straight lacing and round laces.

You will never go wrong with them. 

Also, please experiment with colors! 

Go darker colors and more similar to your shoes to play it safe. 

CustomMade Opening Promotion

We are moving to a new showroom at 82 Telok Ayer St, #02-04. Our opening will be tentatively on 15th May!

Until then, we won't be able to accept appointments. Sadly.

We'll be offering a one time opening promotion. 

This would be available for those who sign up to our list and Like Our Facebook! 
(if you're already on the list,  you don't have to sign up again)

There will be not be any promotional emails of my shoes or 346 different angles of my beautifully crafted CustomMade shoes send to your email.

Just useful content on shoes, being well dressed and updates on CustomMade stories! 

Everything Useful About Leather Dress Shoes

Actionable tips and advice to up your shoe game or for your next shoe shopping experience. 

3 Step Checklist To Find Your Perfect Dress Shoe Fit

4 Factors That Lead To Unsightly Creases And How To Remove Them

How Long Should My Dress Shoe Last? 

Should My Belt Match My Shoes?, Answer By A Shoe Insider