Unlock the Secret Strategy I Use to Build a Killer Dress Shoe Collection for Work Without Breaking the Bank—And How It Can Transform Your Professional Game!

Ever found yourself pondering whether those ‘budget-friendly’ dress shoes on Carousell are a hidden gem or just a fancy way to collect dust? After 15 years of engineering life in sneakers and a half-decade navigating the world of formal footwear—starting off with trusty Pedro shoes and later stepping into the ECCO realm—I found myself on a curious quest. Why not build a rotation of second-hand shoes that not only saves my wallet but also tells a story with every wear? Sure, the idea of someone else’s shoes might raise eyebrows (or even a few superstitions), but what’s the real cost of that risk? Join me as I unravel my adventure into the imperfect yet surprisingly enriching world of preloved dress shoes—a journey filled with unexpected generosity, minor mishaps, and valuable lessons on patience and perspective. Ready to walk this path? LEARN MORE

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As an engineer for 15 years, I don’t really have to worry about wearing dress shoes because most of the time, I am in sports shoes. When I first started in Providend six years ago, I bought a pair of Pedro dress shoes for $179.

The Pedros are really like the entry working shoes if you are on a budget but actually I quite like my Pedro. Aside from that, I visited my colleague Kim and Wenxin not too long after joining Providend, and they had a dress shoe that fitted no one so they gave it to me.

These two pairs of shoes served me for like 5 years. I followed my friend’s advise by alternating between these two pairs but eventually the soles of each gave way. Superglue does not fix the issue but they ended up vital. But there were embarrassing occasions where the soles will come out.

So I decided to buy a new pair and that ended up being the ECCO (which I will share more later).

My experiences with second hand monitors (read here about me getting second hand 24 inch, 2K, 4K monitors if you are interested) eventually made me wonder: What is the downside of buying second hand dress shoes that is reasonably priced on Carousell?

I think the general goal is that if I can build up a fleet of dress shoes over time, and can rotate among them, it should last for a while.

I can take my time, wait for the better deals where the quality is higher than the price, and if the price is low enough.

I was initially concern about hygiene and if I will violate any superstitious rules. The hygiene part went away when I consider how I used it and how most people will use it. I decide to fxxk care about any superstitious stuff.

So I ended up with these bunch of shoes:

This is within 8-9 months HAHA. Probably went too crazy but let me tell you the story of each pair of shoes.

ECCO Queenstown (New) – $155

When my Pedro and the other shoe that my friend gave me broke down, I had to get a shoe.

I wanted to try another pair of shoes around the same price range as a Pedro and I forgot my research process but it lead me down to looking at this ECCO shoe available on Shopee.

Originate from Denmark, ECCO has been known for a balance of comfort, quality and versatility. Reviews have shown that the quality was better last time but in recent years the quality seem to have declined.

I bought it during a Shopee discount for $155 which would have cost $181 without discount. The Queenstown looks like a more reserve, less fancy, working shoe. On hindsight, it feels slightly more spacious and it was this and my next shoe that made me wonder if I might actually fit better in a size 41 or 41.5 shoe.

I am not sure how fast this will decline, but my ECCO is damn light and feels like wearing a sports shoe but for formal setting.

I think this is something what my colleague Yong Cheng and I appreciate about ECCO shoes.

There were days that I have to pre-commit which shoes to wear, and for days where I need little distractions, such as no worry of discomfort, potentially pain due to long walks, I will go with this ECCO.

Roger and Fank Double Monkstrap – $20

Roger and Fank is a Vietnamese shoe maker. Out of all the second hand shoes bought off others this might be the cheapest.

But in April 2025, this was the first pair that I bought for $20. The seller said the price was $120 but i felt it is likely lower than that.

The shoe was size 43 but the guy think it wears more like a 42.

Since my ECCO was size 42 it was really risky going with size 43.

The shoe wears really well after the initial getting used to. This Roger and Fank became my second go-to trashing shoes after my ECCO if I felt that I need walk around a lot.

Atelier Llyr Brown Oxford – $40

Atelier LLyr was a Singapore shoe artisan. Started by 3 people with passion for shoe making (Alan Lee, Alvin Lee and Teresa Chan), they sourced their French Vocalou Calf from the famed tannery, Tannerie d’Annonay and manufacture the shoe at vietnam to keep the price competitive.

They have stopped making shoes locally.

This paid of Oxford is a Goodyear welted construction. Goodyear welted construction is a traditional, high-quality method of making shoes and boots. It’s considered one of the most durable and repairable ways to build footwear. Shoes made this way will have a long lifespan because they can be resoled many times, have good water resistance, comfort.

The gentlemen I bought from kept the leather well, polishing with this sibeh premium Saphir Product. The heel is damaged but it is pretty usable.

I bought from the seller at Claymore Connect for $40.

This shoe is a very comfortable to wear and fits me very well. The downside is that the back of the left side of the shoe is starting to come off (see the picture the back side you will see the strands coming out).

He took care of it so well that it made me wonder what I can do to continue to take good care of it. This was not something that expected to feel, but I think it is something important that I learn from this second hand shoe buying process.

Loake Oxfords and Church’s Men’s Brogues – $80

I saw two pairs of shoes listed with the Church’s Men costing $88 and Loake Oxfords costing $28.

They were both size 41 and they were my attempt to buy the shoes that might fit my feet better.

Church’s Men is one of the oldest shoemakers in the UK. The shoe is Goodyear welted and this pair would have cost a lot of money. They were suppose to last for a lifetime. The seller say this shoe retails for more than $1,000 during its day. Loake is also a UK brand but more entry. The seller says it retails for over £200.

The seller was actually the Head of Debt Markets in a bank and charged me $80 for both.

I thought this was going to be a good purchase. I fitted both shoes perfectly but the problem is that the back of the shoe was rather uneven which eventually caused blisters if I wear them throughout the day.

Thus, they didn’t turn out to be that good of a purchase.

I still have both pairs and am thinking of how to fix the back of the shoe problem.

Moreschi Black Leather Dress Shoes – Free (with some Bus Travel Costs)

I got this pair only recently on 6 September 2025.

The shoe was listed at $10 and I was to go to Bedok South to collect.

Moreschi seem to be black leather shoes that is made in Italy with Vibram soles. If this is really the Moreschi, then a new pair will cost upwards of $200-$300.

You can see in the bottom picture that there is some wear.

I decided not to risk it anymore and stick with a size 42 shoe because if the back of the shoe is not too good, a size 41 one will be difficult to wear.

Turns out the seller was a Caucasian guy who decided to give it to me for free if I have some use for it.

After wearing it this week, I really, really like it, except that the worn out heel was making it too loud in Havend’s wood flooring.

There Were the Duds

I think the Loake and Church’s Men can be considered duds but that is the price I have to pay for less research and being unsophisticated about it.

I think each of us have areas we are either weak, less interested in building up sophistication. We just want it to work. Dress shoes is definitely an area I care less about.

Each of these shoes have their own minor flaws if I am honest and if you are buying second hand, you got to ask yourself where you are with flaws.

I saw this pair of dress shoes that went for $10 and another one that the seller was also selling for $5. So I went down to test and collect the shoes.

The $5 one is a good to have but I wonder how is this quality. This was a size 41, which is my attempt to buy a size that fits me better. The shoe fits well and I decide to purchase it and get the other $5 shoe as well. The owner wanted to give it to me but since he listed it I just transferred $15 to him.

I decided to just wear the shoe on the way back from Pasir Ris.

When I got home, I realized that my socks were all blacked!

Turns out the insides were disintegrating. Basically both pair were unusable. I wasted $15 and a good amount of time.

These two pair of shoes was a real dud but I was not disappointed compared to a deal that didn’t even successfully transact.

There was this seller who listed this pair of dress shoes for $60. The shoe looks to be in pretty good condition from the pictures but I wonder if the size listed would fit me.

So I asked the seller if I could try and if it fits I would buy it.

The seller than told me this is a Bruno Magli and this is one of the good brands. If you Google, the Bruno Magli Oxfords seem to be going for $298 without discount.

So I decided that I will make a trip after work from my office at Duxton… all the way to the east at Siglap Centre to try.

I got there, it was this lady probably in the sixties so we went into the MacDonalds where most likely I get to try the shoes.

Before I even try the lady ask me what I intend to do with the shoes.

So I explain that I want this to be part of my fleet of shoes so that I can rotate and use in the office.

The lady then explains that these are very good pair of shoes and she is looking to sell them to people who genuinely appreciate and use them. She is selling them at a cheap and doesn’t want to sell to people who potentially want to resell.

So i tried my best and explain to her again.

In the end, she said that I don’t look like a genuine buyer.

I decided not to reason with her anymore.

Deep down I was seething because KNN if this is a big deal for you, maybe you should fxxking check with me over the message so that I don’t have to go all the way from fxxking Duxton Hill to fxxking Siglap!

And what do you expect from trying to sell on Carousell?

It is these kind of experiences that made me fear for Kyith as he approaches his sixties.

Epilogue.

I felt that there were more imperfections with my dress shoe sourcing experience than my monitor experience. I would not check the monitors that I purchase much, relying on the law of large numbers that most monitors are in serviceable conditions.

It will also be difficult for me to check a display because where am I to plug into?

Part of the issues was not knowing what are the potential imperfections that could really derail the deal. I seen people who just pay me when I sell things but also those who examine in great detail. If you are paying an amount that is significant to you, then you would check more.

What is the most valuable about buying these second hand stuff is you remember the story behind the purchase, and sometimes the story behind the stuff, told by the seller themselves. Trying to learn more about something you are less familiar with is also part of the story.

While we need the shoes to be functional, comfortable enough, presentable enough, I wonder if buying a new pair of dress shoes would enrich me the same way I get from these second hand buying experiences.

There are research that show people are genuinely more happy with the process leading up to the purchase than the actual purchase. I would say maybe but your positive, and negative experiences, the experiences and memories that you could have because of the tool also enriches your life.

I disagreed with the concept that you should choose to buy experiences and not tangible things. There are stories that you can have because you have an Ipad Mini if that is what you are interested in.

Why do people sell their shoes?

Some just want some cash but through my experiences, I felt that they just want to pass down something valuable and useful so that the shoes don’t go to waste and can serve someone who needs it.

The relationships that they have with their shoes lead them with the hope the next person genuinely would want to use and take good care of them.

If you wish to find the sweet spot, this might be something that you should experiment. You got to accept the imperfections and the risks.

Just like equity, there is a risk you get an ultimate dud, but because of the risk there is a potential of great returns.

If you want to trade these stocks I mentioned, you can open an account with Interactive Brokers. Interactive Brokers is the leading low-cost and efficient broker I use and trust to invest & trade my holdings in Singapore, the United States, London Stock Exchange and Hong Kong Stock Exchange. They allow you to trade stocks, ETFs, options, futures, forex, bonds and funds worldwide from a single integrated account.

You can read more about my thoughts about Interactive Brokers in this Interactive Brokers Deep Dive Series, starting with how to create & fund your Interactive Brokers account easily.

Kyith is the Owner and Sole Writer behind Investment Moats. Readers tune in to Investment Moats to learn and build stronger, firmer wealth foundations, how to have a Passive investment strategy, know more about investing in REITs and the nuts and bolts of Active Investing.

Readers also follow Kyith to learn how to plan well for Financial Security and Financial Independence.

Kyith worked as an IT operations engineer from 2004 to 2019. Currently, he works as a Senior Solutions Specialist in Insurance Start-up Havend. All opinions on Investment Moats are his own and does not represent the views of Providend.

You can view Kyith’s current portfolio here, which uses his Free Google Stock Portfolio Tracker.

His investment broker of choice is Interactive Brokers, which allows him to invest in securities from different exchanges all over the world, at very low commission rates, without custodian fees, near spot currency rates.

You can read more about Kyith here.