A Hands-On, Honest Review of the Oliver Cabell Penny Loafers

Are you looking for a new pair of penny loafers? Don’t overlook the pair offered by Oliver Cabell. Here’s what we think about them.

There are a few pairs of shoes every guy should have in their wardrobe. Even if you have a minimalist or capsule wardrobe, you should have a pair of penny loafers. They are incredibly versatile so that you can dress them up or down, and of course, they’re comfortable. Penny loafers are a dime a dozen, so where do you start if you’re on the hunt for a pair? Luckily, I had the opportunity to give the Oliver Cabell penny loafers a try. 

Oliver Cabell targets the true ‘middle’ in the men’s shoe market. From their original “Low 1” sneakers to Chelsea boots, they have exceptional value by going directly to the consumer. Let’s consider a targeted review of the Oliver Cabell penny loafer. I’ll cover what works, what doesn’t, and whether you should invest in a pair.

About Oliver Cabell

There is no shortage of direct-to-consumer footwear brands. Some are good, and many aren’t. However, not many of them have Oliver Cabell‘s mission. 

Founder Scott Gabrielson was burned out from his job in investment banking. While visiting Asia on a job sabbatical, he saw women making ‘designer’ shoes for under $10 a day. While such tactics aren’t anything new, businesses usually sweep them under the rug. Out of sight, out of mind. But seeing this up close bothered Scott. Why not make a company with transparent pricing? So, he did. 

Oliver Cabell sources its raw materials from Italy’s Marche region, which is well-known for its shoe leather. It manufactures in Portugal and offers a wide range of shoes for both men and women. The designs are classic and fairly conservative—all for under $200. 

But Oliver Cabell’s hook is that they tell you the rough cost breakdown for each pair. Some companies cover this more broadly, but these guys list everything from labor to raw materials. 

What Is a Loafer?

A loafer, in short, is a laceless shoe with a low heel. The history, though, is far longer. Native Americans wore stitched ‘makasins’ (what we today call moccasins) some 4000 years ago. They sat close to the foot, protecting it from sharp rocks, branches, and irritating pebbles. At the time, of course, cobbling wasn’t a thing. A heel didn’t really exist. 

A few thousand (yes, bear with me) years later, a shoe appeared at the excellently coiffed court of Louis XIV.  The Sun King only stood about 5’4” and needed a heel to keep up with his Habsburgian wife, Maria Theresa. His shoes frequently had buckles. While this doesn’t quite fit the contemporary definition of a loafer, it’s a good middle ground. 

The loafer, as we know it, first appeared near the turn of the 20th century. Supposedly, Norwegian fishermen wore them because they were easy to take on and off. Perhaps it was easier to shake the water out. Or because wet shoelaces aren’t much fun. 

The “Weegun” was first mass-produced by GH Bass & Co in the 1930s. Because the term “hippie” didn’t exist yet, Ivy League students in the 1950s began to wear the “loafer” as a symbol of rebellion. The rogues even stuck pennies in the slits of the vamp. Hence, the ‘penny loafer.’ 

Loafers today come in a range of styles. For the more traditional take, try a tassel loafer with a small braid on the vamp. East Coasters in the United States might be familiar with the unstructured Belgian loafer. If you like your shoes specialized or are a car guy, the driving moc is a good option, too. 

You can change your silhouette, too. Traditional penny loafers have a rather short vamp and toe box, but more modern versions stretch it. 

Oliver Cabell Penny Loafer Review

With some necessary context, let’s dive in. Now, when Oliver Cabell approached us and offered to send these penny loafers, I’d expected to have a couple to work with. Not because I need more (I don’t…really…ask my wife), but it’s difficult to fully evaluate a shoe brand based on one model. I also usually try to get two different sizes, especially as I’m a rather difficult customer to fit. But they only sent one, so we’ll work with what we have.

Styling

Loafers can come in any color you can think of, but the most common are black and brown. I’ve got brown loafers pretty well covered, though. Black is having a bit of a revival, so I figured I’d try it. 

Proportionally, it’s a well-balanced pair of shoes. The vamp and toe box aren’t ultra-long. This is quite nice for me, as I do have longer, narrow feet compared to my 5’7” (172-ish cm) height. Longer, exaggerated lasts can look a little clownish on my feet. But, the vamp and tongue aren’t so low I feel I’m going to step out of the shoes. 

The toe box itself has a soft, slightly rounded shape. This is, again, perhaps the most classic Ivy or Weejun-inspired design. I appreciate Oliver Cabell going in this direction. More aggressively styled brands tend to have long, almond-like shapes to their toes. It gets into pointy ‘spear-like’ territory pretty quickly. On the flip side, a chisel-y toe can become square pretty quickly, too. This is about right.

While the Oliver Cabell penny loafer has correct proportions, this pair has a few questionable styling details. 

I don’t understand the design choice for white stitching on the black background. It unnecessarily casualizes the shoe and makes it a little harder to style. I think it also cheapens the look. Luckily, other models don’t have this. I’d definitely go with ‘Jet black.’ It could have also been my fault for not double-checking on the exact product request. 

I’m also not a fan of the colored tag on the outside here. Again, it unnecessarily casualized the shoe. It’s not a deal-breaker and far less noticeable in other colorways. But this stark white tag on the black background still sticks out where it shouldn’t.

Build Quality, Construction, and Materials

A number of direct-to-consumer companies tout their use of full-grain Italian leather. It’s exotic, unusual, and the phrase “Made in Italy” exudes elegance and panache regardless of whether or not Italians are making your shoes. Oliver Cabell sources full-grain leather from the Marche region of Italy. Located on the country’s eastern side, Marche is well-known for shoemaking and good-quality leather. 

Oliver Cabell manufactures their penny loafers (and all their shoes) in Portugal. It doesn’t hold the same clout as, say, Italy or Spain. We at TMM definitely had an issue with one now-defunct shoe brand. But that’s not an issue here. 

All in all, I’ve found the penny loafer from Oliver Cabell to be pretty well-made. The stitching is even all the way around. There are no loose threads or anything to snag on.

The leather upper does feel nice enough. It’s soft and rather pliable out of the box- but holds its shape after you flex and move. I’ll have to wear them a little more to see how a patina develops- good leather adds quite a bit of character as it ages. 

The Blake-stitched (they call it ‘hand-stitched) doesn’t feel great or give me much confidence it’ll hold up the way the heels on some Thursday pairs I have. I like the idea of a rubber sole-less slipping on office floors. But, a hybrid leather and rubber sole with a stacked heel would be a much more premium product. Certainly, economic factors might make this a steep ask, but it would be worth it for a longer-lasting shoe.

Fit and Comfort

As readers of my shoe reviews will know, I’m not an easy foot to fit. With comparatively narrow and flat feet, some direct-to-consumer brands can be a bit difficult. 

Oliver Cabell penny loafers come in whole sizes, from 6US (38) to 15US (48). Usually, if given the choice of a regular direct-to-consumer brand in a “D” width, I try for a 9.5/42.5 in laceless shoes. I went for a 42 here. Going up to a 43 would have been the better choice. 

While the footbed is plenty comfortable, my foot does go nearly all the way to the end. You can see where it bows out on the side. 

Ideally, I’d like to see half sizes. But that may not be feasible and would, perhaps, add more to the per-unit price. 

Cost

Speaking of price, the Oliver Cabell penny loafer costs $179.99 at regular price. 

Oliver Cabell is phenomenally transparent on their average per-unit cost. 

• Upper: $7.14
• Interior Lining: $3.72
• Rubber Outsole: $3.24
• Labor (Cutting, Manufacture, QC): $17.88
• Packaging: $3.96
• Transit: $11.43
• Customs/Duties: $4.36
• Shipping: $11.50

Total: $63.23

Given the general business rule of thumb at 30% per unit cost of the sale cost, this largely tracks with a $180 retail. But, these are still sub~$200 dress shoes. While that’s not a drop in the bucket, the brand made a few sacrifices to hit the price point (namely, the rubber sole). 

After a routine discount or various promo codes, you can snag these loafers for around $160.

Wrap Up: Is the Oliver Cabell Penny Loafer Worth It? 

Oliver Cabell penny loafers offer a decent value proposition. The leather is soft and pliable, and the insoles are comfortable. The styling on my sample pair probably isn’t the most versatile, but there are other options. I’m not sold on the rubber outsole on my pair, and I think the budgetary constraints show up there. 

If you’re between sizes, fit might be an issue. It definitely was for me. But if you have a regular-width foot and most loafers tend to fit you well, these should fit.

Here at TMM, we try to give the reader a range of clothing and footwear options. We look across the spectrum and consider styling and budget when selecting your outfits. However, these are a good place to start if you’ve only got $150 or so to spend on dress shoes.

Thanks for reading.

Have you worn Oliver Cabell’s penny loafers? What are your thoughts on them? Let us know in the comments below.