The Summer Loafer: A Jay Butler Shoe Review6 min read

Hailing from my hometown of Philadelphia, Pennsylvania — Jay Butler has been making waves in the world of #menswear ever since launching in late 2014.

The Summer Loafer: A Jay Butler Shoe Review | GENTLEMAN WITHIN

Founder Justin Jeffers, who’s also the man behind The Fine Young Gentleman, has been in the menswear blogging game since early 2011. That’s over 6 years, which is a long time in internet years.

I recall stumbling upon his blog a few years back while researching various made-to-measure, custom suiting companies, but didn’t realize he launched his own shoe brand. If you want to know more about Justin and how he went from his blog to brand, check out this inspiring interview over on The Buttoned Up Podcast.

For a quick look at the loafer in video format, hit the play button below.

Jay Butler Cromwell Penny Loafer Sneak Peek | GENTLEMAN WITHIN

In this review I’m going to touch on 3 key components of what I think makes a great shoe—the style, the construction & quality, and the price. And how Jay Butler fares in each category.

But first, allow me to drop some knowledge on the penny loafer and its origins.


Jay Butler Cromwell Suede Loafers | GENTLEMAN WITHIN
Jay Butler loafers conveniently come with a canvas carrying bag and shoe horn for easy slip-on.

The penny loafer is a classic warm weather shoe that’s ultra comfortable, can be dressed up or dressed down, and worn on a multitude of occasions. Whether at work, at a wedding or wandering about the monuments at Washington DC, it’s the type of shoe that you can literally wear all summer long.

I’ve only begun to embrace the loafer in recent years and it’s quickly become a summer staple in my book.

It has two dressier siblings, the tassel loafer and the bit loafer which can be worn more formally with suits, but still retain a casual stance since they’re slip-ons after all. Finally there’s the opera pump which is a formal loafer mainly worn with tuxedos. In any case, the penny loafer remains the most ubiquitous of them all.


Penny Loafer Tribes Through History | GENTLEMAN WITHIN
With its versatility, the loafer through time has been embraced by style tribes from the preps all the way to the punks | credit: Esquire

Exactly a century after America declared independence from England, the penny loafer originated under the Bass brand. They didn’t reach mass market until 1936 going by the name of “Weejuns,” short for Norwegian.

it or not, they were originally worn by Norwegian fishermen and later adopted by preppy ivy league students. Today, loafers are worn with everything from swimwear all the way to custom suits.

Did you know? Word has it that the leather strap running across the front of the loafer with the little slit had a function—to hold, yep you guessed it, a penny—which conveniently at the time was how much it cost to make a phone call.


During the shoe break-in process, I wore my Jays down the shore on a beach trip w/the fam., slid them on a trip to Baltimore for a business meeting, and took them out to the driving range—Appropriate for such places if ya ask me.

Scroll through the images above to see some of my #JourneysWithJay so far.


When Justin asked me what style shoe I wanted to test drive, my first choice was the olive green suede Cromwell penny loafer, which is one of their seasonal colors (Fall 2016), but to my dismay there weren’t any in my size.

I decided to go with the versatile dark brown suede Cromwell penny loafer. Suede because it’s more breathable than the full grain leather, making it ideal for the summer heat. I opted for dark brown, albeit a bit more formal than a light brown, but more versatile.

If you know me then you know I’m all for versatile pieces that can be dressed up or dressed down. Justin also kindly threw in a matching belt. It has the same nap feeling as the shoes, complimenting them perfectly.

Personally, I like how the Jay Butler shoes remain true to the classic loafer silhouette with a few subtle modifications.

Jay Butler Goes Golfing | GENTLEMAN WITHIN
JFK wore ’em on the golf course, so can I. | photo by: Morgan Brown

Jay Butler loafers distinguishing features:

  1. Lower vamp—(vamp is the piece of leather that covers the top part of the foot) Creates better balance between foot and shoe compared with other loafers I own that have higher vamps.
  2. Thinner sole & lower heel—The thinner sole sacrifices a cork cushion, but makes for a sleeker look than other loafers out there. And lower heel is more elegant than a chunky one.
  3. Padded insole—To make up for the lack of a cork sole, there’s a padded insole that provides cushion from heel to toe, molding to your foot over time.

These are small details, but make a big difference to any discerning man.


Justin looked into India & China and thought about Spain & Portugal as potential factories to work with. He found the right fit for Jay Butler in Mexico, where their shoes are handcrafted. He said they were nice people that were honest and forthright about their businesses.

Mexico seems to be doing a pretty good job with the construction. The shoes are lightweight, flexible and durable. I’ve worn these loafers for a good three weeks now and they’re even beginning to mold to my feet.

Recently a pair of loafers from Cole Haan that I’ve been wearing for 2 years now, cut the back of my ankle up pretty good. It happened because I was walking aggressively for a long distance.

But with the “Cromwell” loafers from Jay Butler, I’ve had no discomfort on the back of my ankle, even during the break in period. The comfort and support for my achilles says a lot about Jay Butler’s construction.

Jay Butler Leather Sole | GENTLEMAN WITHIN
Although you may sacrifice a bit of comfort and and traction, I feel a leather sole looks more elegant than rubber.

Jay Butler loafer attributes:

  • Leather sole (Classier than a rubber sole)
  • Hand sewn suede upper (means a more careful attention to detail)
  • Blake stitched outsole (allows for resoling when the leather wears out)
  • Combo heels (half leather and half rubber—gives the feel of walking on leather with durable qualities of rubber)
  • Full-length padded insole with arch support (for lasting comfort)

The bottom line: 
The Jay Butler “Cromwell” suede loafer feels as good as it looks and there’s a nice nappy texture that I can tell is going to age well.


If you ask Justin, his goal for Jay Butler was to create shoes for gentlemen under $200. Mission accomplished. With shoes ranging from $145-$195, (minus the exclusive made to order exotic shoes) he created an affordable loafer without compromising on construction, quality of materials and style. A hard feat to achieve in the world of menswear.

$200 seems to be the sweet spot that most men are willing to spend, who know that they need to upgrade their shoes, but aren’t willing to drop $300+. My take is that Jay Butler is a quality shoe brand that sells stylish loafers at an affordable price point.


  • Wear pants with no break while wearing loafers. It makes for a cleaner, more streamlined look. It’s most aesthetically pleasing in my eyes.
  • Go sockless—it’s summer, it’s fun. Show a little ankle. If you must, you can always go with the trusty no-show socks.
  • With Jay Butler’s, I recommend sizing up a half size since they run a bit small. I got my usual 7.5 at first and they were too tight, I went with the 8 and they’re kosher.
  • Relax and have fun with your style. The loafer’s casual nature reminds me that it’s just clothes at the end of the day.


Jay Butler At The Driving Range | GENTLEMAN WITHIN
photo by: Morgan Brown

Finding a sub-$200 shoe that’s well made, well styled and well priced is often difficult. And Jay Butler manages to check all 3 boxes. In the future, I see Jay Butler continuing to grow as they make waves in the menswear industry. Right now they have loafers and matching belts, but in time I can see them expanding their offering. We’ll see.

If you have any questions, as always, you can reach me at khoi [at] gentlemanwithin [dot] com. I’d love to hear from you.

A note: The shoes and belt in this review was complimentary. These are all my own thoughts and opinions based on my experience and some online research.


Let’s continue the discussion over in the Gentlemen Within Private Facebook Community.

Looking forward to seeing you in there.


Get more posts like this plus style tips & advice delivered straight to your inbox.

100% privacy. No spam. Unsubscribe at anytime. Powered by ConvertKit


  1. J. Plybon says

    I’ve purchased 5 or six pair of Jay Butler loafers and dealt with Justin directly. Two things that were important to me; 1.) Justin is hands on and personable and has mastered the fine art of customer service. 2.) I own (and have owned) a great deal of loafers and Jay Butler loafers are incredibly comfortable, stylish and the price point is awesome for the quality. Keep up the good work Justin and the Jay Butler crew! Thank you for your incredible service and shoe. Cheers!

    • Khoi | Gentleman Within says

      Wow, 6 pairs of Jays. You’re spot on with the customer service. Justin is a great dude with a quality product. Thanks for sharing your thoughts! Will be sure to pass the good feedback onto his team.


Drop a Line!

This site uses Akismet to reduce spam. Learn how your comment data is processed.

%d bloggers like this: