The 3 Most Important Points Before Shopping For A Quality Leather Dress Shoe In Singapore

Every men need a good looking pair of formal dress shoes

But most don't know the difference between an oxford and a Siberian deer.

(trick question...there is no such thing as a Siberian deer)

These are 3 things you need to know about men formal shoes for your next shoe shopping trip.

1.      Style & Design

2.      Construction

3.      Leather

Lastly, and most importantly, what is the purpose of your shoe?

Is it for formal work, smart casual wear

or you simply just have $300 in spare change...



This is where the purpose of your shoes play a part.

You want the style/design to fit the purpose.

Certain styles are more casual, while some are more formal in nature.

While style is not the only factor in how casual/formal a shoe is,

It plays a fair part.

These are the general styles of dress shoes:

1.      Oxford - closed lacing (most formal)

2.      Derbys - open lacing

3.      Monkstraps - buckles

4.      Loafers - no lace and buckles (least formal)


Designs of a shoe refers to its intricate pattern on the upper (main leather part).

There are two main kinds of designs -

  • Brogues (shoes with perforated holes) and drumroll please....
  • Non brogues.

For designs, less is more formal.

The front of the shoe which is the main part has 4 main different designs

1.      Captoe

2.      Wingtip

3.      Apron toe

4.      Plain

These designs are independent of whether the shoes are brogued.

KEY POINT: Style is more fundamental while design refers to the patterns on the shoe.

They are independent.

KEY QUESTION: What purpose am i getting the shoe for? 

If its formal office wear, get a cleaner design and oxford style

If its smart casual, you can experiment and go for brogues and derby/monkstraps

There is no such thing as a one shoe fits all. 

You can't have a shoe that is both formal and casual at the same time....

It just doesn't work that way. 



Construction is the method used to make the shoes.

Different constructions require different machines, techniques, labor, etc

And have their own respective pros and cons.

There are 3 main kinds of construction

1.      Cemented - found in most Bata shoes and buildings.

2.      Blake Stitch - found in most Italian shoes

3.      Goodyear Welt - found in most British shoes

KEY POINT: Try to stay away from cemented shoes.

They typically do not last long and break down after a heavy downpour. 

KEY QUESTION TO ASK: What kind of construction is this shoe made of? 

Note: Some designer brands of a higher price point use cemented construction



The most important part of a leather formal/dress shoe!

Typically, most premium leather formal/dress shoes would be in full leather which means:

1.      Upper - the main part

2.      Lining - the inside of the shoe

3.      Sole - the bottom

These would all be in leather.

Having them in leather means more breathability (airy) and also, over time,

it would mold to your feet, giving a more customized fit.


There are 3 grades of leather

1.      Full Grain (highest quality)

2.      Top Grain

3.      Corrected Grain (lowest quality)


KEY POINT: Stay away from corrected grain leather.

They tend to flake and peel off after a short period of use.

(some designer brands of higher price point use corrected grain) 

KEY QUESTION TO ASK: What kind of grain leather do you use for this shoes?

(note that corrected grain also means genuine leather)

Don't mean to brag but hey, my CustomMade shoes are made out of full grain calf leather.

(actually i did mean to brag).  


KEY TAKEAWAY: Know the purpose of buying a pair of shoe and shop accordingly while keeping these 3 things in mind.

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.

Opening Promotion (2).png

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)

Useful Information About Men Dress Shoes


3 Step Guide To Find Your Perfect Dress Shoe Fit


How Long Should My Dress Shoe Last


4 Factors That Lead To Unsightly Creases And How to Prevent Them


Should My Shoes Match My Belt, Answered By A Shoe Insider

3 Easy Ways to Match Your Socks With Your Shoes And Pants Perfectly

Poor matching socks with a bespoke suit and good looking shoes weaken the entire presentation. 

Like a weak link in a chain. 

We know that socks are important in your presentation

The first question is "should they match my shoes or pants?"

Should My Socks Match My Shoes Or Pants

1.) Your socks should match the color of your pants. 

Because they are an extension of your pants. 

A consistent sock - pant colour would not interrupt your silhouette. 

Giving you a more consistent, less jarring look. 


2.) If you're wearing a lighter colour pants, you can match your socks to your shoes. 

e.g. If you're wearing beige pants or khakis, you don't need to wear beige socks

These are just the "safe" rules.

However, multi colored socks with different patterns are good looking

And i'll show you a few ways to pull them off. 

3 Ways To Match Your Socks


This is the safest, most fool proof method. 

Choose a pair of socks that is either a shade lighter or darker than your pants. 

E.g. if you're wearing a charcoal grey pants, pair it with a charcoal socks. 

Or a sky blue socks for your navy blue pants. 

This is a formal, professional and elegant look

But it might appear boring. 

Good for: Interviews, formal meetings, etc



Coordinate doesn't mean match. 

Your socks don't have to be the same shade of color with your pants or shoes. 

But it is nice if there is natural symphony. 

Think of colour complements and contrast.  

Alternatively, introduce some patterns or texture to your socks. 

You can follow the tonal principal, but add a subtle strip or polka dot. 

Or use a thicker socks to team up with heavier material like denim. 

Just remember that textured styles can add weight to a look. 




Integrate some bright and bold colors into your outfit. 

An easy introduction would be to pick patterned socks in the same base color as your pants. 

You can go further and opt for vibrant colored socks that is complementary to your pants. 

Remember, your sock color must be complimentary or contrasting correctly. 

Think of the color wheel. 

Pro-Tip: Neutral coloured pants would be easier to match with bright coloured socks. 

It is less likely to go wrong. 

Neutral colors are black, white, tan, grey.

Key Takeaway: Socks are important to an outfit. 

You can revamp your presentation without breaking the bank with socks. 

Just take note of the colors and always play it safe when in doubt. Go tonal. 

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.

Opening Promotion (2).png

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)

In 95% of social situation, the well dressed man is king

Where there is only one climate in Singapore, being well dressed is easy

3 Key Principles To Be Well Dressed in Singapore

The 5 Mins Principle To Be Well Dressed With Colors For Every Outfit in Singapore

The Ultimate List to Find Your Perfect Fit For All Your Clothes

The Well Dressed Man: Should My Belt Match My Shoes?

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?