Initial Impressions, Jay Butler, Stitched Footwear

Jay Butler Cromwell Penny Loafer: Out of the Box

Disclaimer: It’s generally accepted that there are several great choices in the $300 range for penny loafers, and to stay away from everything in the $100 range. Wondering about the middle, I asked Jay Butler if they would be willing to provide a pair of their Cromwell Penny Loafers for review, and they agreed.

Jay Butler Logo


  • Price: $195 MSRP
  • Pros: Amazing materials, Extremely competitive price
  • Cons: Runs small


If you’re looking for the long term review of these shoes, we did a follow up after 100 wears here.


If you go on Styleforum, Reddit, or any other well-known website and you ask about any budget penny loafer, you’ll generally get the same response. The responses given say that the $100-tier shoes are “plastic garbage.” Generally, people are told that if you want a penny loafer that isn’t made with old newspapers, you need to step up to the $300ish dollar price point. No doubt there are great options there, and we’ve reviewed several of them.

Of course, most people would guess that something designed to be sold in an outlet mall for less tan $100 is going to be a bad investment. And, of course, most $300 loafers will be good. I couldn’t help but wonder about the pricing in between. Where does something for $200 land on that scale?

Thankfully, I’m not alone in that. There is a brand that targets that specific market.


Founded in 2014, Jay Butler was part of the crop of brands that started right when men’s fashion was really taking off again. Focusing entirely on loafers (at least from a footwear perspective, they also sell other things), they have managed to keep everything but the exotic leathers under $200.

The question is, should their $200 loafer be discussed as an affordable alternative to the “Big 3” Made-in-Maine options? Or is this just a more efficient way to get rid of money than the $100 brands? Let’s find out.

Jay Butler Cromwell Penny Loafer
Jay Butler Cromwell Penny Loafer


The Jay Butler Cromwell Penny Loafer aims for a slightly different look than most handsewns. Something more in line with a city than a hike. This design focus is something that you can see and feel throughout the shoe.

One of the first things I noticed when I pulled it out of the box is that the moc toe stitching is short and even. I’ve previously stated that a bit of unevenness on a moc toe doesn’t bother me on reviews here, and I stand by that, but it does set a tone for the shoe. Just a few inches behind the toe, 5 loops hold the beefrolls, and the strap that runs between them, tight.

Jay Butler Penny Loafer Toe
Jay Butler Cromwell Penny Loafer – Tight and Even Moc Toe

The front of the shoe is also part of the signature look – the low/short vamp. Considerably shorter than other loafers I own, it lends itself towards a slightly relaxed look. They are certainly more at home with chinos and shorts than a cuffed suit. It might be possible for some to make them work with a more casual suit, especially in a different material, but in the short time I’ve had them it’s been beyond my ability.


Moving back, the throat of the shoe features a fairly standard design with a piece of suede around the collar. The stitching here, like elsewhere on the shoe, is straight and even. As good as any of the “big 3.” The back of the shoe features another piece of matching suede to hide the stitching, again a fairly classic penny loafer design.

Extremely long-haired suede makes up every exterior panel of the upper. It’s very soft to the touch, and feels great in hand. The color has a tendency to change a bit depending on light, with it being browner in direct sun and greener in the shade. It’s also nearly impossible to capture a color accurate photo. I’ve included both sunlight and shade in the pictures, but the reality is somewhere in between.

Olive Green Jay Butler in the Shade
Jay Butler Cromwell Penny Loafer – Shade

Out of the box, the suede had worn a bit on the rear of the shoe from rubbing during shipping. It’s not the end of the world, and came out with a bit of brushing with a suede brush. It’s still a lot better out of the box than my Alden Indys.

Inside, the lining is a tan, glove leather. This leather is incredibly smooth, and covers every surface of the interior of the shoe. The heel of the non-removable insole features the Jay Butler logo.

Moving to the bottom of the shoe, the tan outsole features brown edge dressing around the sides. In line with it’s more city-oriented aesthetic, the upper overhangs the sole a bit in just about every location. This overhang is most noticeable over the heel, where the shoe pinches in visually quite a bit.


It’s also worth noting that they offer a belt in every leather that they offer their shoes in. Not a huge deal if you’re getting brown or black, but a nice choice to have if you like green or red suede.  

Jay Butler Cromwell Penny Loafer – Non-Corrected Color in Sunlight

Fit & Comfort:

These shoes fit tight. Very tight. I’m an 11.75D brannock, ordered a 12 and, even with no socks, they were only just barely big enough. These are anywhere from a half size to a full size smaller than comparable Maine-made loafers, depending on how wide your toes are.

I have no doubt that they will stretch a bit and end up comfortable. Though, that is the same way I felt about my Quoddy bluchers. Those are a full size smaller than these, and I wear those with socks.

I can’t knock them too much about this, they offer free shipping and exchanges. However, on your first try I would certainly suggest going up rather than TTS or down.

The reason I kept these, though, and didn’t size up is the lining material. It is amazingly soft. Marshmallow Fluff soft. It would be a crime to wear these with socks and miss out on that softness. It’s my favorite part of the shoe.


It’s also my biggest concern, but we’ll get to that later.

Elsewhere, the comfort is about what you’d expect with such a thin sole. You feel the ground, and there is very little impact protection outside the liner. It’s better than the Quoddy True Penny – it has actual arch support – but don’t expect to walk miles in these.

Jay Butler Loafer interior
Jay Butler Cromwell Penny Loafer Interior – Note the Thick Material on the Tounge


The materials on the upper of the Jay Butler Penny Loafer were the biggest surprise for me. Pulling them out of the box they feel extremely high quality. Jay Butler has done a great job in picking their materials.

They are also thick. The suede and the lining combined are 3.8 mm (.15 inch)! Other than the double-layered tongue of the Rancourt Boat Shoes we reviewed a few weeks ago (which hit 4.0 mm), this is the thickest handsewn featured on this site. It’s as thick as my Indys. Thankfully, that thickness doesn’t translate to stiffness. Even with the nearly half a centimeter of leather and suede it is soft and pliable.  

I do have my concerns here though. The materials are almost too soft. On the interior, I am concerned the soft leather might not be the hardiest material. Especially when worn sockless like I plan on doing. I will be wearing these throughout the winter – salty roads and all. Expect an update to see if these concerns are founded.


Along similar lines, any ultra-thin sole could be fast wearing. I don’t have any reason to believe this will end up one way or the other, and this is a design choice not a cost saving feature, but it’s something to keep an eye on.

On the other hand, this sole features something I’ve never seen before. In most blake-stitched moccasins, the heel sewing is much further in compared to sewing around the forefoot. This leaves an area for water to enter and dirt to build up.

This shoe has something different. Attached to the heel at the back of the shoe there is a piece of leather that almost looks like a welt. This fills the area that would normally allow for buildup, and will help prevent water entry.

I’m not sure if this was the intended purpose of this piece, but either way I’d like to see more manufacturers do this. It seems like a really cost-effective way to solve this issue.

Jay Butler Cromwell Penny Loafer – Note the Leather Piece Between the Heel and Upper

Ease of Care:

While suede can look amazing, it also is a material that requires significantly more care than leather. Expect to clean these shoes fairly often if you’re wearing them in regular rotation. Generally, you’ll want to give a full cleaning every couple of months or so.


The procedure to clean starts with brushing with a suede brush, or an eraser if the dirt is really bad. Once the dirt is removed, wet the leather and use a soft brush and suede shampoo. Rinse off the shoe, and use the brush to get the shampoo out of the suede. If you’d like to bring back the nap, brush again at the end.

There are suede protectors that you can spray on as well, though for this pair I’ll be leaving that off for the long-term review.

The other wear point on these shoes is the sole. As a blake stitched shoe it is resoleable, though Jay Butler doesn’t currently offer a factory option to do so. You’ll need to find a cobbler that has a blake machine. Many do not, so it’s smart to call ahead.

Of course, you’ll want to use shoe trees in these whenever you’re not wearing them. If possible, as with any leather footwear, try to give a full 24 hours rest in between wears.

Jay Butler Sole
Jay Butler Cromwell Penny Loafer Sole


As mentioned above, the Jay Butler Cromwell Penny Loafer is priced at $195 dollars. This puts it substantially lower than the normal prices of Quoddy ($275), Rancourt ($295), and Oak Street Bootmakers ($328).

From a price standpoint, the most comparable product is probably the Thursday Lincoln ($170). That being said, the Lincoln is a very different loafer style-wise. Personally, I prefer the handsewn/moc-toe look when it comes to loafers, so I wouldn’t cross shop these, but others might.

Jay Butler Olive Green Corrected
Jay Butler Cromwell Penny Loafer – Corrected Color in Sunlight


One of the key selling points of the Jay Butler Penny Loafer is their value proposition, and they don’t disappoint. The materials on particular pair are really nice, especially for the price point. While it’s true that you are giving up something compared to the more well-known brands, you’re also knocking around $100 dollars off the price.

When it comes to comparable brands, Thursday is slightly less, but the style isn’t for me. As I’ve said in other reviews, if you don’t like the product it doesn’t matter if it’s free.

Resoling using blake stitching is typically more than a goodyear welt shoe. Each city is going to be different, but I did call a few random cobblers around the country. Prices ranged from $60 to $120.

Jay Butler Box
Jay Butler Cromwell Penny Loafer

Wrap Up:

The Jay Butler Cromwell Penny Loafer has amazing materials for a really competitive price. While it certainly isn’t true that every loafer in the $200 price range is a good purchase (looking at you To Boot), this pair shows that it is possible.

If you’re looking for a handsewn with good materials and a reasonable price, Jay Butler is definitely worth checking out.