Every man needs a quality pair of dress shoes. But how do you tell the signs of a good dress shoe?
If you don’t know what you’re looking for, chances are you’ll just end up judging based on price. And if that’s all you’re looking at, most likely you’ll end up overpaying.
Recently, I had a chance to try a pair of shoes from Beckett Simonon. Full disclosure, Beckett Simonon sponsored this article, but they had no input on the content and they didn’t know what I was going to say. Fortunately for them, I really like their shoes.
In fact, I think Beckett Simonon shoes are a great example of the 4 things you need to look for in a quality pair of dress shoes.
Watch the video below or continue reading.
1. Quality Leather Upper
The first thing to look for in a great dress shoe is a quality leather upper.
Not surprisingly, the material the shoe is made of is pretty important. You’ve probably noticed, there are all different types of leather for shoes, and it can be pretty confusing:
- Full grain?
- Top grain?
- Genuine leather?
What do these even mean?
Let’s start with the worst first:
Genuine leather is basically third-class leather. It is real leather, but it’s not as high-quality. It’s essentially what remains after they split off the higher-quality parts of the leather and is sometimes spray-painted to look like higher quality leather.
Next, there’s top grain leather. This is what’s left after they sand down the top of the leather to get rid of the imperfections. One advantage is that the look is more uniform, so it’s good for mass-market products, but it’s not quite as strong, and it doesn’t have as much character since the outer layer has been removed.
Finally, the best leather to look for is full grain leather. This comes from the top layer of the hide. So it’s going to have more imperfections and nuances, but it’s also going to have more character. Over time it develops more of that rich patina that you expect from great leather. It’s also the strongest and most moisture-resistant type of leather.
This graphic from Real Men Real Style helps put things in perspective:
Beckett Simonon Caine Oxfords
The shoe I received from Beckett Simonon is the Caine Oxford, and it’s really an elegant shoe. It seems to be their take on the classic cap-toed Oxford, which is a pretty timeless style. (to learn more about different styles of dress shoes, The GentleManual has a great article here).
The Caine Oxfords are full grain leather and they’re also vegetable-tanned and chrome-free, which means your skin—and the workers who make them (if that matters to you)—aren’t being exposed to harsh chemicals.
If you’re interested in trying Beckett Simonon for yourself, you can use offer code DISTILLED to save 15% off your order. Visit the site now.
2. Stitched Leather Sole
The next thing to look for in a great dress shoe is a stitched leather sole.
The construction of the dress shoe is very important to the quality. There are basically three types of construction: cemented or glued, Goodyear Welted, and Blake Construction.
As you might guess, cemented or glued soles are more commonly seen with less formal, more disposable shoes like sneakers and casual shoes.
For dress shoes, you want to go with either Goodyear Welted or Blake Construction because:
- they’re stronger and will last longer, and
- it means you can replace the sole
If you’re going to invest in a nice pair of dress shoes, it’s kind of a shame to throw them away just because the sole wore out, right?
It’s almost like spending a bunch of money on a car, and then sending it to the scrap heap just because the tires wore out.
If the shoes are stitched with Goodyear Welting or Blake Construction, you can give your shoes a second life (or even a third or fourth) by re-soling them.
With Goodyear Welting, an extra layer of leather called the “welt” is sandwiched in between the outsole and the insole and all three are sewn together with the upper. You can usually tell because you’ll see the welt sticking out with stitching around the outside of the shoe.

This is probably the sturdiest type of construction but it also ends up being less flexible. And because of the extra labor and steps involved, it’s usually the most expensive.
The Caine Oxfords have a durable leather sole and use the other main type of construction method: re-solable Blake Construction.
With Blake Construction or the Blake Stitch, as it’s sometimes called, a leather upper and insole are sewn directly to the outsole. So the stitches are inside the shoe. This sometimes means you can have a narrower profile since you don’t have the welt sticking out around the edge. And because it is less complicated than Goodyear Welting, it is usually less expensive.

3. Natural Leather Lining
The third thing to look for in a great dress shoe is natural or leather lining.
Having natural fiber like leather in the lining helps a lot in terms of making the shoes comfortable and also more breathable to help avoid odor. The Caine Oxford’s actually have a full-grain leather lining that makes them extremely comfortable and breathable.
4. Affordability
The final thing to look for in a dress shoe—at least in my opinion—is affordability.
When you don’t know what to look for in a quality shoe, this might seem counterintuitive—because again, you’re probably using price as your primary measurement.
While there may be SOME correlation between price and quality, the truth is, most shoes at retail have a 200-300% markup. So the extra cost you’re paying doesn’t go towards the quality of the shoe.
What you’re actually paying for is the cost of:
- carrying inventory
- paying rent in stores, and
- hedging against risk

Think about it: When you mass-produce shoes ahead of time, you don’t know if everything’s going to sell. So you have to price the shoes in a way that makes up for that potential “waste.”
Beckett Simonon keeps their shoes extremely affordable because they don’t have all these extra layers of cost. The average order is between $160 and $199, for shoes that would easily be $300 or more in a traditional retail environment.
They can do this because all of their shoes are made to order. So they don’t carry any inventory, they’re not paying rent for some fancy store, and they eliminate waste since they only manufacture the number of shoes that get ordered.
Here’s how it works:
Each month they release about 8-12 new styles they’ve designed in-house. You select what you want, choose your size, and place your order.
The hard part is, you do have to wait. It takes about 6-8 weeks for the shoes to be completed. So if you need shoes for a wedding that’s happening in 3 days, this isn’t going to work—you best head to Nordstrom.
I know what you’re thinking:
There are other crowd-funding or pre-order models like this, and they have their share of issues.
First, usually, they have minimums. If not enough people place orders, they can’t do the production run. But Beckett Simonon doesn’t have any minimums because they own and operate their own factories.
Also, unlike other pre-order arrangements, Beckett Simonon actually offers free returns and exchanges, which is pretty generous if you think about it, considering that you custom-ordered those shoes.
The other interesting thing Beckett Simonon does is that they involve you in the process.
Co-founder Nicholas Hurtado told me he calls this “backstage access.” Rather than waiting for 6-8 weeks and not hearing anything, you get periodic email updates about what’s going on with your shoes. They tell you what stage they’re in, they share videos so you can see the process, and you even see the faces of the people who are actually making your shoes…which is pretty cool.
Beckett Simonon: Turning Over a New Leaf
If you’ve known about Beckett Simonon for a few years, there might be an elephant in the room that needs to be addressed.
When I started researching Beckett Simonon, I noticed that there were a handful of reviews and forum threads around 2014 or so that were, let’s just say, less than positive. I heard stories about a few people who weren’t satisfied with the shoes or frankly the experience.
But then, I noticed something else:
Some of the reviewers who initially had complaints a few years ago were now updating their reviews and saying good things. Like my friend Justin over at The Fine Young Gentleman, who incidentally knows far more about shoes than I do, since he owns and operates his own shoe line.
When I spoke to one of the co-founders, Nicholas, he explained that their original model was much different:
They weren’t doing their own manufacturing back then. They were working with a vendor in India, and the quality didn’t end up being up to their standards. Since they were still outsourcing the creation of the shoes (like most brands do), as Nicholas said, they “lost control of the most important part of the product.”
Personally, I think they were also challenged to be able to service all the orders they received initially and weren’t set up to maintain quality and customers service.
But now their process and their business model are entirely different. As I mentioned, now they actually OWN the factories and are responsible for all aspects of the shoe creation. In many ways, they are an entirely different company.
Now they are focused less on quantity and speed, and focused more on value and quality.
As Nicholas told me, “We have less sales volume overall now, but I like to think we have better customers.”
I have to say, the more I learned about this company, the more I really appreciate what they’re doing, and—let’s be honest—the fact that they learned from their mistakes. Not only are the shoes beautiful, well-crafted and reasonably priced, but I think the way they run their business is really refreshing.
If you’re interested in trying out the Beckett Simonon experience for yourself, you can use offer code DISTILLED to save 15% off your order. Click here to browse this month’s styles.
Kyle, Great lead on shoes. Ordered a pair from Beckett Simonon. Their customer service was outstanding. Lance
That’s great to hear, Lance! Glad you had a good experience so far! Would love to hear your thoughts once you get your shoes.
I perfer Magnanni