Beckett Simonon vs Jack Erwin: I Test & Compare Both Brands

Direct to consumer brands aren’t a new concept, and over the years, several boot and shoe brands have come and gone.

But there’ve been a few that stand out: Beckett Simonon is one that comes to mind.

Beckett Simonon has long been one of my favorite brands, and I recently had someone ask on the BootSpy YouTube channel how they compare to Jack Erwin shoes.

I hadn’t heard of Jack Erwin before, but they’ve been around for the better part of a decade, so I figured it was time to try a pair for myself and settle the debate.

Beckett Simonon and Jack Erwin Overview

Beckett Simonon

Beckett Simonon has a unique business model that allows them to make high quality shoes and boots at a relatively low cost. But it’s also kind of annoying if you need your boots in a hurry. 

Let me explain.

All Beckett Simonon boots and shoes are made to order. So when you order your new boots, they don’t actually have them in stock—they have to send that order to their factory in Colombia so it can be handmade and shipped right to you. 

You might have to wait anywhere between 6-12 weeks. When I ordered my two pairs of Beckett Simonons, each took more like 6 weeks, but I’ve read some comments from others who had to wait longer. 

The downside of this practice is obvious: it takes longer to get your new boots. 

But the upsides are worth it in my opinion. 

Beckett Simonon doesn’t have to keep a massive stock around, which is usually the biggest expense for any company. So they’re able to cut down on the cost of their entire line as a result because they don’t have to add margin to cover a huge range of styles and sizes. 

After owning boots from entry level and high end brands alike, I’d say that Beckett Simonon really stands out because of their leather quality at their price. The construction is solid, but the leather is buttery soft and looks incredible. 

Beckett Simonon leather outshines all other brands I’ve tried in the $200-$300 range, and I’d put it more on the level with $300-$400 brands. 

So for me, Beckett Simonon is one of my favorite brands because of their unique ability to deliver superior leather compared to similarly priced brands. But you’ve got to have some patience to shop with them. 

Jack Erwin

Jack Erwin has been around for almost a decade, but I just heard about them. Looking through their catalog, it seems like Jack Erwin produces new models based on current trends.

Through research, I’ve seen Jack Erwin pop up in debate amongst other direct-to-consumer brands, though they’re not really in the same category—the brand has their shoes made in Portugal, and they don’t run the factory as far as I can tell. 

I was a bit disappointed in their selection of boots (I’m a boot guy, after all). They had three styles of Chelsea boots, but no lace up boots at all. 

Like many brands out of Portugal, Jack Erwin boots and shoes are made with a Blake stitch construction and high quality leather. 

I’ve had the chance to try two pairs of Beckett Simonon’s, and I only own one pair of Jack Erwins: the Ellis Chelsea. So while I have more experience with Beckett Simonon, I still think my perspective on the two brands will help you make a choice between the two. 

Features Face to Face

Style

Obviously there’ll be some major style differences depending on which models I’m discussing, but I’ll give an example to support my feeling that Beckett Simonon’s design and shape is more sophisticated.

Let’s compare the Beckett Simonon Douglas Jodhpur to the Jack Erwin Ellis Chelsea.

Check out the toe box on both:

The Beckett Simonon (in black leather) has an angled toe, which is similar to many other high end brands that are popular in Europe and London. It’s not as pronounced as I’ve seen with other brands, but the subtle slope at the end of the toe gives the Beckett Simonon a unique shape that’s sleek and stylish without being cookie-cutter. 

The Jack Erwin Ellis is exactly what you’d expect from a slim, narrow-toe Chelsea. I’m not disappointed with it, but I’m also not impressed. It’s basically identical to my Ace Marks Troy, and is also similar to the first pair of Chelsea boots I bought for $60 back in the day: the shape is super common. 

The Jack Erwin Ellis is a good looking boot, and I really like the color of the leather. But Jack Erwin’s Chelsea is like most other Chelsea boots out there, whereas the Beckett Simonon Bolton Chelsea has a little unique flair to its style. 

Leather

Leather quality is the big difference between these brands. 

I should start by saying that the Jack Erwin Ellis Chelsea uses high quality leather: it’s all full grain calfskin with a nice leather lining. And for the price, you’re getting solid value for that kind of leather. 

But Beckett Simonon is a special brand in that they use exceptional quality leather for boots and shoes close to the $200 mark. 

It’s worth repeating that they’re able to use that high quality leather and keep their prices lower because they hand-make their boots to order, meaning it can take 1-3 months to get your order. While that might be an inconvenience, it’s a fantastic way to get what feels like a $350 boot for only $200. 

There’s no break in time with either brand: they were both immediately comfortable. Though I noticed that my Jack Erwin boots developed deeper creases because of the stiffer leather. Beckett Simonon leather has a creamy smooth texture to it that I haven’t seen with many other brands, and because of that, they crease gently. 

Sole

The sole quality and construction is quite similar, so I can’t say one brand beats out another in this category. 

Both Beckett Simonon and Jack Erwin boots are made with Blake stitch construction, and while you could technically have each resoled, it would cost nearly as much as a new pair of boots from either, so it’s not very reasonable. 

My Jack Erwin Ellis boots have a rubber studded sole with a nice balance between firmness (for durability) and give (for grip and comfort). The rubber stud sole makes this much more of a casual boot, though most people wear Chelsea’s for casual purposes anyway. 

The Beckett Simonon Douglas, on the other hand (foot?), has a leather sole, which makes it a bit more formal. 

Leather soles typically do terribly in poor weather and rain—if they get soaked through, they can be damaged easily. But they also make for a more formal option. 

I never wear my Chelsea boots in bad weather so it doesn’t make a difference to me, but it may be worth considering which sole you’d prefer. Just to be clear, though, you won’t ruin your leather soles if you get caught in a rainstorm—but repeated exposure to water is harder on a leather sole than a rubber sole. 

Shopping Experience

Besides the 6-12 week shipping time from Beckett Simonon (which, to be honest, is a pretty major “besides”) both brands offer a similar shopping experience.

You can expect free shipping, free returns, and free exchanges from either brand. You have 30-days to return your boots but you must make sure they’re not creased or look worn in any way.

For that reason, I recommend trying your boots on at home on a carpet. That way you won’t scuff up the sole but you can still feel if they’re comfortable or not. 

You can check out my in-depth Beckett Simonon sizing guide if you’d like to see how to get your best fit there. 

Which is Best for You?

If I had to choose between the two brands, I’d go with Beckett Simonon. Their boots have much higher quality leather at a very similar price. 

The construction quality isn’t all that different (they both use Blake stitch), so that’s not really a factor. 

The big downside with Beckett Simonon is their lengthy wait time, but it’s also how they’re able to add leather that you’d normally find on a $300+ boot and put it in a ~$200 package. 

Otherwise, there was nothing about Jack Erwin that felt unique or special—the Ellis Chelsea was decent, good quality leather, nice construction, and pretty comfortable. 

But considering that you can pick up the Beckett Simonon Bolton for just about the same price, but you’ll get a more sophisticated shape and much higher quality leather, I think the choice is easy: Beckett Simonon all the way.