What’s the Best Penny Loafer for Your Budget? (2025)
Updated for 2025
From the 1980’s until recently, the penny loafer has been in a bit of a weird position in men’s fashion. It wasn’t casual enough to replace a pair of sneakers, and it wasn’t formal enough to replace an oxford. The penny loafer pretty much only resided in the closets of preps and wall street bankers. Often, they were the same people.
Today, however, things have changed. In a world where even Goldman Sachs doesn’t require a suit, the Penny Loafer has found a new life. Fitting perfectly into the business casual environment of most offices, the penny loafer is a go-to for a lot of men.
However, for such a simple shoe, there is a baffling range in prices. From Sperry Topsider models that go for $50 to Edward Green models that retail for more than $1,200, if you have a budget there is a penny loafer that fits it.
If a penny loafer isn’t really your style, be sure to check out our Best Oxford for Your Budget and Best Service Boot for Your Budget alternatives.
Let’s take a look at our picks for the best penny loafer, no matter your budget, as well as a few other great options.
What’s the Best Penny Loafer Under $200
It used to be that this category was a bit of a throw away. The Weejuns had some history, so maybe they were worth considering, but otherwise this was just to try the style before you bought something below.
While Thursday has now succumbed to the inflation bug, at least slightly, they still offer great value here. The Lincoln Penny doesn’t have quite the same build quality as their main-line boots. Still, this is a lot of loafer for the money.
Of course, not everyone needs a loafer that will last years. Maybe you want something for once or twice a year. If that’s the case, the G.H. Bass Weejun does the best job at capturing classic style with an affordable price.
The Weejun was the first shoe that could be called a penny loafer. It’s genesis. Over the decades Bass has lowered the quality, moved production overseas, and increasingly focuses on name recognition, but that doesn’t change the history.
If you’re really looking to save some money, picking up whatever is at Nordstrom Rack for $50.
What’s the Best Penny Loafer under $250
While this price point will still come with compromises, that extra bit of money allows brands to differentiate themselves. Three loafers that I really like in this space are Jay Butler’s Cromwell Penny Loafer, and the Meermin Calf Penny Loafer.
Ultimately, both of these offer a great penny loafer for basically the same price. Meermin’s offering wins out to me due to the durability and resoleability. However, if you want a more subdued slim style, the Jay Butler option is still great.
What’s the Best Penny Loafer Under $400
Credit: Oak Street Bootmakers
- Winner: Oak Street Bootmakers – $348
- Quoddy True Penny Loafer – $349
- Rancourt Beefroll Penny Loafer – $328
What an absolutely stacked range to pick from. Honestly, not only are there a number of great options in this group, there really isn’t any reason to go beyond it unless you really want one of the other brands for some reason.
Personally, I would still go with the Oak Street Bootmakers, though it’s really personal preference between them, Quoddy, and Rancourt. Especially now that OSB and Rancourt are made in the same factory. All of these are the classic American loafer. It just depends on if you want one that’s very built up, sort of built up, or very flexible. At different points in my life I’ve had each of these be my favorite shoe in my entire collection. If you’re looking for more information comparing these three brands, click here.
Credit: Rancourt & Co.
What’s the Best Penny Loafer under $500
- Winner: Grant Stone Traveler – $412
- Alden Leisure Hand Sewn Seconds [Requires Shoemart Log In] – $419
A category that was once one of the most packed when I first started this list has become one of the most empty. The good news is that there are two great options here.
In this category, I’d be going for the Grant Stone Traveler. I personally find the fit of these two be among the best of any penny loafer out there. In fact, the nearly identical Tassel Loafers are one of my favorite pairs 100wears has ever looked at. Review Here.
If you don’t want Grant Stone for whatever reason, Alden 2nds are available for basically the same price. To access them you need to make an account at the Shoe Mart. However, unlike most seconds, there are typically a lot of options to pick from.
What’s the Best Penny Loafer under $800
- Winner: Alden Leisure Hand Sewn – $710
- Alden Leisure Hand Sewn Seconds (Shell Cordovan) [Requires Shoemart Log In] – $519
- Crockett & Jones Boston – $740
For loafers over $500, expectations are justifiably high. These options do not disappoint. It’s tempting to suggest the shell cordovan LHS seconds as the obvious choice. However, it’s simply impossible to ignore what the Alden Leisure Hand Sewn brings to the table when you’re not limited to seconds.
Depending on your retailer, you can find them in more than a half-dozen colors of suede, numerous calf options, or various chromexcel colors. The soles come in rubber or leather, with all of Alden’s edge dressings, and you can even pick if you want lined or unlined depending on if you like socks. No matter what you’re looking for, it’s likely that you’ll be able to find a non-shell LHS that fits your need in this price bracket.
The only real drawback to the LHS is that the Van last on which it’s built. It’s wide in the heel and narrow in the mid-foot. The Crockett & Jones Boston offers a more elegant last, and could end up being more affordable outside of North America.
What’s the Best Penny Loafer Any Price?
- Winner: Alden Leisure Hand Sewn (Shell Cordovan) – $947
- Crocket and Jones Harvard – $1,100
- Edward Green Piccadilly – $1,520
At this price point, you’re paying for small details. And, sometimes, you’re paying big money for small details. Buying any of these is an emotional decision, rather than anything else.
When it comes to emotional connection, many would say that the Alden Leisure Hand Sewn in shell cordovan can’t be beat. I’ve bought a pair myself – full review here. It will last your entire life, and your son will wear them as well. They work with a suit, blazer and slacks, or chinos and a sweater. If you’re lucky enough to get them in Whiskey or Ravello, they can even be worn with shorts. For many, they are the pinnacle of the loafer.
There is nothing negative that can be said about the others on this list. Picking a winner is like picking your favorite ice cream flavor. There is no right answer and no matter what it’ll be good. All of these options are almost certain to have impeccable construction and materials. If you don’t love the Alden – and at this point you really should love what you’re getting – either of these other shoes will serve you well.
Credit: Edward Green
Straightforward and well written, thank you for the info
Hey, I thought nettleton actually invented the loafer, although they’re in a weird spot, as their reputation was made in Syracuse, NY and now everything is in Belgium.
Hey John –
This might deserve it’s own post, but I love diving into this. In the early 1900’s a Norwegian man combined the teser – a kind of clog worn by lower income folks in Norway – with an Iroquois moccasin and started selling these “Aurland Moccasins” in Europe (they didn’t look like what the brand offers now, but they did have the moc toe and strap). Several companies – including both Nettleton and G.H. Bass – saw this and had the idea of adding a stiffer sole and leathers to this design. While Nettleton was one of the early ones and may have independently thought up the idea, G.H. Bass was the first to launch what we think of today as a penny loafer (1936 for Bass vs 1937 for Nettleton).
Nettleton can get a bit pedantic in saying they sold the first “Loafer,” because they came up with the name “Loafer.” Much like G.H. Bass has the “Weejun” or Alden has the “Leisure Hand Sewn,” Nettleton’s version of the shoe was marketed as the “Loafer.” It’s just that the name was put on a product that already existed.