Often, shoes they’re the first and the last thing people will notice when they see you, and as such, it pays to get it right. For us, getting it right means that you have a quarterly pair of leather shoes.

In fact, my first pair of good quality, Goodyear-welted shoes were from Church’s. They were a black, cap toe Oxford that I bought from eBay back in the early 2000s. I heard about the brand Church’s from the book “Gentleman” by Bernhard Roetzel, and you can learn more about that on our website.

Back then, I didn’t have any money, so buying a used pair of Church’s was the only way for me to get a quality pair. Today, I no longer have to buy used shoes. I can buy new shoes made-to-order, ready-to-wear, I even ordered bespoke shoes, but I still buy used shoes.

For example, one of my recent acquisitions was a pair of Gucci loafers that we found at a local vintage store when Jack from our team was in town, and it cost a whopping 38 dollars. Over the years, I learned a thing or two about buying used shoes – what not to buy, what to pay attention to, and in today’s video, I want to share that with you.

I’d like to discuss reasons why you should buy used shoes and reasons you may not want to buy used shoes. I also share my strategy to find great shoes and avoid the lemons. Obviously, in the internet age, there are thousands upon thousands of opportunities to buy shoes new and used online, and if you want to learn about all my eBay tips and tricks, you can check out this in-depth video here. Those tips apply to all sorts of shoes, including sneakers. This video is more about classic-style men’s dress shoes.

Now, our cameraman is a sneaker aficionado, so not only do I get a good glimpse at the different sneaker models out there, but I also understand that it’s an entirely different ball game. And if you’re one of those persons who feels yucky about used shoes, check out this video where Preston shows you how used shoes or sweaty shoes are not yucky anymore.

Why Should You Buy Second-Hand Shoes?

1. Great Way To Save Money

Frankly, there are various reasons, but the biggest and number one reason is that you can save a great deal of money. Yes, retail prices mean nothing anymore when it comes to use shoes.

For example, this pair of loafers from Ralph Lauren Purple Label was made in England by Edward Green; retailed somewhere in the neighborhood of 1850. The pair was worn once or twice, it still came in the original box, and I paid 250 dollars – meaning a savings of 86.5%. At the end of the day, quality dress shoes are just like expensive cars. They depreciate a lot the minute you drive them off the lot, so why not let someone else take that big hit initially?

Now, there are rare occasions where you can find the specific model and style that you want from a specific brand, in the size you want, in the width you want, at the time you want it; however, if you’re not in a hurry and you can be patient, you can save searches on eBay for your favorite brands and sizes, and eventually, you will find great stuff at low prices.

Also, don’t forget, because you’re now buying from secondhand shoe vendors, you can do something that’s not really common in retail – you can barter! You can ask questions, strike up a conversation and maybe you get even a better deal than before.

To learn about all my tactics, check out this video here.

2. Gives You Access To More Brands

For example, if you’re interested in vintage styles, you can get a old Florsheim or Johnston & Murphy shoe, which is of a much higher quality than their modern counterparts. Also, if you think of higher-end classic men’s shoe brands such as Edward Green or Gaziano & Girling, you may find a style online that is no longer available in their current lineup.

For example, I bought a black pair of Gaziano & Girling brogue shoes with the original shoe tree that fits the last. They retail from around 1300 to 1400 dollars. I paid 250 dollars for them, so that’s a savings of at least 80%.

Honestly, many these high-end brands can be found at dramatic discount, and this is how everyone on the team in the Gentleman’s Gazette has amassed a large portion of their shoe closet. Because, sometimes, you may want to get this really cool spectator shoe, but you don’t want to spend full price on it, but you’re used to quality, so buying them used or gently used is the way to go. Which brings us to the third reason why you should buy used shoes.

You can get unusual styles and express your unique take on style without having to break the bank by going bespoke. So, for

3. Access To Unsual Styles

Finding a spectator loafer new is hard; most brands don’t carry it. So, you’re left with a made-to-order option or going custom, and there’s a good reason. Most brands wouldn’t be able to sell a lot of ready-to-wear loafers in a spectator pattern, so they just don’t do it. Or maybe look at lazyman shoes. They are typically hard to fit, so most ready-to-wear companies don’t offer them and you have to go made-to-order or bespoke.

I found this very gently-used Gaziano & Girling lazyman. The style is in Melbourne under the TG-73 last. This shoe, including the shoe trees, costs about 200 dollars. I paid 300 dollars. So that’s at least 85% off. Would I have bought these shoes at 2000 dollars? Absolutely not! I would have opted to go bespoke, but since they were available for 300, it’s a good way to get a style that I may not have in my wardrobe yet, in maybe a cool leather, or something unusual that I may not get as much wear out of, but I still want to enjoy

Maybe you want something that’s a bit more casual or unusual. For example, a kiltie loafer without the tassels. This is a style I found from Paul Stewart, made in England. I think they were made by Grenson.

On their website, their made-in-England shoes retail for around 895 dollars. I paid a hundred bucks shipped, so that’s roughly savings of 88%. Personally, really like having unusual items, and I don’t just want to have three pairs of shoes in my wardrobe. So buying used pairs of shoes allows me to express my style, to get maybe a pair of shoes that only works with two or three outfits in my wardrobe, but I know when I have them, they’re really really cool.

For example, this spectator loafer was made by Edward Green England for Barney’s New York. I would say it’s at least 20-25 years old based on the whole branding and the way things look, but they’re in great shape. It’s a kiltie loafer that has kind of a monk strap buckle and is a spectator. I mean, you’re not gonna find that today anymore.

4. Breaking-in Is Less Of An Issue

If you’ve ever had a pair of new Allen Edmonds shoes before that was Goodyear-welted, you know what I mean when I say, new Goodyear-welted shoes may need a break-in period. Yes, I know many shoemakers now have a softer Goodyear option, but I still feel it needs to be broken in. Why? Because it’s leather, it’s a natural material, it’s stiffer at first, but it’s much more comfortable once it’s broken in. And yes, even bespoke shoes need break-in time, even though it’s not as much as some other shoes.

Of course, if you buy a used pair of shoes that has been worn a few times, this work is already done for you. As a fun fact, many years ago, wealthy gentlemen would have their staff pre-wear their shoes so they would break them in for them. They bend and flex the sole and the uppers just so the shoe would be more comfortable.

Now, you may even have heard of the trick of peeing in your shoes to make them fit better, and that’s what maybe servants did back in the day. No, Preston! I’ve already broken those in.

Some shoes on the second-hand market are new old stock, meaning they’ve never been worn or they’re very gently worn, they’ve only been worn a few times, but the vast majority is already well broken-in.

5. It’s More Sustainable

Now, if you’re interested in becoming more green and more sustainable, keep in mind that nothing is as green as the shoe or the clothes that have already been made. No additional resources are necessary to produce them and, as such, they’re much better than any new thing you can make.

6. More Retailers are Dedicated to Selling High-quality, Used Clothing

Fortunately, in recent years, there have been more local retailers or even online merchants who specialize in used clothing. In the US, you even have stores like Leffot, which sell new shoes but also have a use section; in the UK, you have Abbot’s, which is like an online emporium for used clothing; or you can have physical stores like the beautiful Rudolf Beaufays vintage store in Hamburg, Germany. By the way, we visited there, and you definitely don’t want to miss the cool look of that store.

Why Shouldn’t You Buy Used Shoes?

Now, naturally, life’s about a balance, so let’s take a look at the drawbacks of buying used shoes and why you might not want to buy them.

1. Hygiene

Yes, I know the biggest concern is that some people think use shoes are icky or yucky, but again, Preston made a video that shows you how you can get a used pair of shoes fully hygienic. And yes, there are limits to that.

For example, personally I don’t buy used boat shoes because boat shoes, you typically wear just barefoot in the summer, so you sweat a lot into them. It’s in the leather. So, I only buy new boat shoes.

2. Buying Online Can Be Tricky

Another drawback of used shoes is that the whole buying process can be admittedly quite difficult, especially if you buy them online and you can’t try them on.

With clothes, you can go to the alterations tailor; with shoes, you can go to a cobbler, but there are limitations as to what they can do.

Yes, you might get them stretched a little, but there’s only so much you can do before you destroy the shoe. You can also maybe add an insole; or Preston, for example, he adds pads to his heels and over the vamp just so he makes his loafers fit for example. In any case, you won’t be able to change a shoe from size 8 to size 10 or form 43 to 45.

Even if the sizing seems right in the listing, you may not quite exactly know what you get because sometimes, over time, brands change their lasts and their sizing slightly, and you don’t know about that; or maybe the brand made the shoe for a different company.

So, let’s say, the made-in-England Edward Green makes a shoe for Paul Stewart, but the sizing Paul Stewart wants was US sizing. So, now, it’s all confusing.

Sometimes, the person who lists the shoes online may not be an expert and so the details may not be accurate. Therefore, it’s always advisable that there is a returns option. Even if it’s paid, at least you’re not out all the money if the shoe doesn’t fit. Of course, it’s always best to shop for vintage stuff in person, but that limits you to your local retailers or maybe if you visit a store while traveling.

3. Unknown History

The second challenge when buying used shoes is that you don’t know how the previous owner wore the shoes and how they cared for him or potentially didn’t care for them at all.

Of course, if there are obvious flaws like, if the sole is worn through and there’s a big gaping hole or if there is a rip in the upper, you can immediately see that and you stay clear of that. And frankly, if you can’t see that, maybe it’s time for an eye test.

Other signs of wear are a bit more subtle. Typically, you start by looking at the soles first.

Personally, I always stay clear from shoes that have been resoled because I don’t know how many times they’ve been resoled, I don’t know if the job was done properly, and it’s impossible for me to ascertain that just from the picture. So, I look for the original sole.

Typically, brands have a stamp, there may be some painting at the bottom, and you can see how worn the sole is. If there’s a channel, on a Goodyear-welted shoes, it’s the stitching, are they walked through or not? Otherwise, how can you really understand what a sole looked like?

That requires more knowledge and you have to understand, maybe an Edward Green, typically, has this sole brand new from the factory. And when they make it for Ralph Lauren Purple Label, this is what it looks like; and in twenty years, that’s what it looks like. But, as you go through the listings, you get an understanding of what is the original sole and what isn’t.

I also check the tip of the shoe because, if that is worn, I know immediately that it’s not something would want to buy. I also check the heels and see how they are worn. Are they scraped, are they coming off, do they need an immediate repair, or are they basically brand new?

A sure way to find out if a shoe is only gently used or not is to look at the lining. Because of the sweat of the feet, typically, when you wear shoes a lot, it darkens, and if the inside of the lining and the sole are in very good shape, I can tell this person has only wore them a few times max – maybe just once or twice – and the shoe has plenty of wear left.

Now, even if the lining is in great shape, but the outside has been neglected. Maybe they left the shoes in the sun, and they never polish them. Now, the leather is dry and crackly, and and you see those deep ridges or even some openings. That’s a sure sign for me to stay away because likely you’ll just run into issues with those shoes.

Sometimes, people also just sell the shoes that they’ve worn a lot and are now done using to someone else, who maybe just wants the brand but isn’t so sure about what to look for in a used shoe.

Also, keep in mind, hardly anyone is going to say, “Hey! This is a completely worn-out shoe. Now, here, please give me some money for them.” That’s why it’s good to have a general understanding of how a pair of Goodyear-welted shoes or quality pair of leather shoes are made and how much it costs to a repair, and you can watch some videos here on our channel or even follow other cobblers to just see what goes into something and what is a good stage to buy a shoe at and what is something to stay away from.

When I started out buying used shoes, I definitely bought some that were more used than now because they were less expensive. Now, when I buy a pair of used shoes, I pretty much only go for “worn once or twice” or “gently used.” I don’t go for anything that needs a repair. I still save a lot of money compared to the retail price, but I pay maybe just slightly more. And often, they still come with the original shoe trees and I know exactly what I can expect.

4. Sizing Can Be A Mystery

The third reason why you may not want to buy used shoes is that sizing can be a crap shoot. Obviously, even the best shoe is worthless for you if it doesn’t fit. Now, especially quality men’s shoe brands have different widths different sizes, and over time, they might add lasts and maybe discontinue some, and so things get a bit more convoluted.

Not all sellers disclose what kind of last was used, so it gets even harder. But, keep in mind, you can always ask. The inside of the shoe will typically have the information that you want.

To be fair though, even when you buy a new pair of shoes, trying on all the different models and widths and sizes can be challenging and, for a clotheshorse like me, can take an entire day. 

Now, for argument’s sake, let’s say you know what lasts you like in a brand and what size. If you are going to buy a used pair of shoes, especially an older shoe, maybe it was owned by someone who was quite heavy, maybe they had a very wide foot and they had a shoe that wasn’t really wide enough, so that will now stretch the leather and impact that shape that you thought works for you but now, no longer does. It’s a useless pair of shoes. They molded to the previous owner’s feet, not to yours.

The same is true with the heel. Maybe they had a really wide heel, maybe you have a slim heel, and now, that doesn’t work anymore.

So, in my book, that’s just another reason to only go with very gently used shoes because then you know the previous person didn’t really change them from the factory setting in any meaningful way.

As I mentioned before, certain lasts get discontinued or changed. There are probably hundreds if not thousand pages on the style forums where people say, “Hey, if I have a Crockett & Jones size 11 in this shoe, what should I go with with Edward Green?” And it can be helpful, but finding the right information can be quite tedious, and nothing is as good as having experience.

So, in the beginning, I would really stay with shoes that you can return; even though you pay for the return, it gives you the chance to try things on and to understand, “Oh! This works!” and “This doesn’t work!” But, personally, sometimes, I’m even surprised because I’m like, “Hey! I wear Edward Green in this size, in this last,” and then I get the shoe and it fits slightly differently.

Other Tip When Buying Used Shoes

Now, that we’ve discussed the pros and the cons of buying used shoes, here are a few more things to consider.

1. Not All Leathers Are Alike

There are very fine calf leather, there’s cheaper calf leather, or there is cowhide, which is even less expensive. Also, the thickness of the leather and how it feels and how it was tanned can be quite different. So can be the toe caps – some can be stiff, others can be soft. The soles – some are really stiff, others very flexible.

2. There’s More Than One Way To Make A Pair Of Shoes

Just because it’s Goodyear-welted, doesn’t mean it is a good quality shoe. If you want to get a hunch about different brands, what we recommend, what we like, please check out our ranking videos or our “Is It Worth It?” videos, so you get a good understanding of what makes sense and what maybe doesn’t make sense.

That being said, with used shoes, you may be able to buy a John Lobb shoe that you would never buy at retail price. but now that it’s used, you still get a good quality shoe at a lower price.

3. You Don’t Have To Settle With What You Buy

Keep in mind, you don’t have to settle for what you buy; sometimes you can buy a used shoe with the intent to maybe strip the color and then put a vintage patina on it, right? And it’s much easier to do that or even experiment with it on a cheaper used shoe than on a new pair or in a crust leather pair.

You could also make little changes – such as polishing the shoes, adding some edge painting, or exchanging the shoelaces to something that make them look unique and different. For a selection of quality shoelaces, please have a look at our shop here.

4. Upfront Cost Is Rarely The Final Cost

Also, keep in mind that the upfront cost is rarely the final cost. If you buy online, there’s shipping involved. There may be free shipping, there may be paid shipping. There is taxes involved. And in terms of time, when you get the shoes, maybe you want to polish them, maybe you have to apply edge painting. Maybe you have to go to the cobbler. This is all something that goes into the final cost of the shoe.

So, that bargain shoe that needs all these repairs – new polishing, a new heel – may end up costing you more in time and money than if you had just bought a new pair, maybe on sale or a pair of seconds.

5. Value Your Time

Outfit Rundown

Fort Belvedere

Yellow Exotic Caribbean Boutonniere Buttonhole Flower

SHOP HERE

Fort Belvedere

Moss Green Silk Wool Pocket Square with Printed geometric medallions

SHOP HERE

Fort Belvedere

Madder Silk Tie in Green with Blue Orange Motif

SHOP HERE

Keep in mind, money is not the only resource you’re investing here but it’s also your time. Just searching for second-hand shoes can be a huge endeavor, and you can maybe get obsessed with it. And it’s very easy to go down the rabbit hole. If that’s your hobby or you do it during your off time, cool. But, just something to be cognizant of.

6. Be Careful With Used Bespoke Shoes

So, what about bespoke shoes? Should you buy used bespoke shoes? After all, most bespoke shoes are generally made to a much higher standard of craftsmanship and workmanship than a factory shoe. Yes, they’re typically hand-welted, they have unique styles, the leather is going to be good quality, and oftentimes, it sounds like a super enticing deal.

However, keep in mind, this shoe was made for the original customer, and no human being has identically mirrored feet. So, it’s even more of a gamble than buying a sized used shoe. Even the best made shoe in the world is of no use to you if it doesn’t fit your feet.

Now, on the flip side, most bespoke customers don’t just have one pair, and sometimes, lots of bespoke shoes come up at a huge price advantage. And sometimes, they can’t be returned; sometimes, they can.

You can ask for measurements just to create an idea of how wide is their shoe, how long is the shoe, and so forth to get an idea of whether it might fit you or not. And maybe you want to risk it, buy one pair even if you can’t return it just to see if it fits you. Because if it does, you can probably get the whole lot at a discount because you buy all of them, and they know they have a hard time selling them anyways because they are bespoke.

Also, you can go and ask bespoke shoemakers if they have any pairs of customers that were never picked up. Or for example, when we were at the bespoke shoemaker the other day, Amara Hark Weber, who made a whole series of shoes with me, which you can check out here, said that her feet grew after her pregnancy, and so she had a bunch of shoes.

Teresa tried them on and she said, “Wow! This is the best fitting shoe I ever had,” and so we scooped up some pairs, which was really nice for us, of course. She can make new shoes for herself, but these are all things to consider, especially when you can try the shoes on in person because then you see immediately if they fit you or not.

One more important note on bespoke shoes: If you buy them used, check the heel height and if they’re different, or if you have differences. Because the last thing you would want is buy a pair of used bespoke shoes that then will cause hip or back pain for you.

Where Can You Buy Used Shoes?

So, what are good places to buy used shoes from? I mean, obviously there’s eBay, there’s Poshmark, but there are also lots of other smaller stores that are more curated, and we’ll have a list of all the stores that we have personal experience with and our corresponding post on our website.

Outfit Rundown

In today’s video, I’m wearing a nice sport coat from Brioni that I got second-hand. It’s paired with a linen-cotton striped shirt in light blue and white. I’m wearing a pair of Prince of Wales check pants in kind of a linen-cotton blend, which is in a nice high-rise cut. It’s a prototype for Fort Belvedere, and it’s paired with a pair of khaki and navy socks and a pair of second-hand Gaziano & Girling shoes I bought for $300 on eBay. It’s that Melbourne style.

It was a made-to-order shoe on the TG-73 last. It has this cool rubber sole that is very flexible, so it feels more like walking with sneakers than with a classic dress shoe. But, it has the look of a classic dress shoe. It’s also a lazyman style, which is not something you will find very often.

The leather has this beautiful hatch grain. It has this dark, deep, rich reddish brown tone, and it has the beautiful pointed cap toe, which is typically something you only see on bespoke shoes because the uppers have to be pulled exactly centered over the last; otherwise, it will look off.

My watch is a vintage Gruen Precision with a brown lizard strap that picks up on the color of my shoes. I’m also wearing a ring with a white stone. The metal is gold just like the parts of my watch, so everything is harmonious and works together.

Last but not least, I’m wearing a pocket square from Fort Belvedere that is hand-rolled and has hand-embroidered polka dots in blue. For my cologne today, I’m wearing the Roberto Ugolini High Heel White, which is a beautiful unisex scent that has tones of vanilla and is available in our shop along with other Roberto Ugolini fragrances.

Outfit Rundown

Fort Belvedere

Navy and Khaki Shadow Stripe Ribbed Socks Fil d'Ecosse Cotton

SHOP HERE

Fort Belvedere

White Linen Pocket Square with Blue Hand Embroidered Polka Dots Spots

SHOP HERE

Fort Belvedere

Roberto Ugolini – Kitten Heel

SHOP HERE

Do you wear used shoes? What do you believe their pros and cons are? Have you scored any great deals? Let us know in the comments!