What’s the Best Penny Loafer for Your Budget?
Updated for 2022
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.
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 $150
It’s hard to specifically recommend anything within this price range. To keep the price this low, significant compromises need to be made in materials, construction, or – most likely – both. On a cost-per-wear basis, these shoes will almost certainly be higher than the next few tiers. And, they won’t look nearly as good.
To make matters worse, with the recent inflation, the Weejun has gotten worryingly close in price to the next tier up.
Of course, not everyone needs a loafer that will last years. Maybe you want to try out the style first. 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 $30.
What’s the Best Penny Loafer under $200
- Winner: Jay Butler Cromwell Penny Loafer – $195
- Meermin Calf Penny Loafer – $195
- Thursday Lincoln – $168
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, the Meermin Calf Penny Loafer, and the Thursday Lincoln.
For my money, I’m taking the Jay Butler. Leaning a bit towards a Northeastern style, the Jay Butler is the closest in style to shoes further up the list. We have a more in-depth review coming soon [UPDATE: now live], but in addition to the style, the materials are great for the price point. What you’re giving up is the country of manufacture, and the limited resolablity of the construction.
If you’re looking for something that is a bit easier to keep going long term, both the Meermin Calf Penny Loafer and the Thursday Lincoln come with a goodyear welt. While not aligning with the preppy/nautical vibe many penny loafers aim for, both of these should last for many years of wear.
What’s the Best Penny Loafer under $300
- Winner: Grant Stone Traveler – $288
When this was first published this was the spot where all the big brands lived – but in the past two years almost everyone else has gone up in price, leaving the Grant Stone Traveler the sole quality option under $300 – and that isn’t a bad thing.
The Grant Stone Traveler offers great build quality and easy resoling at a really attractive price. Even more impressive, while just about everyone else on this this has raised their prices by 20% or more since 2020, Grant stone has gone up a much more reasonable 3%
While I have not had a chance to review a pair of Grant Stone Travellers here, the nearly identical Tassel Loafers are one of my favorite pairs 100wears has ever looked at. Review Here.
What’s the Best Penny Loafer under $400
- Winner: Oak Street Bootmakers – $336
- Quoddy True Penny Loafer – $300
- Rancourt Beefroll Penny Loafer – $315
This bracket is where you are going to find the heavy hitters of the Penny Loafer world. The “Big 3” from Maine – Oak Street Bootmakers, Quoddy, and Rancourt.
Really, you can’t go wrong with any of them. All three have a great history and are known for making great products. If you’re looking for a more in depth comparison, take a look here. It just depends on what you’re looking for.
Quoddy makes the most classic “Made-in-Maine” look, Rancourt will be the most presentable at a more formal event, and Oak Street Bootmakers lands somewhere in the middle. My personal favorite at the moment is Oak Street Bootmakers since I keep getting older and appreciate the greater support, but I’ve owned and loved all three. If you want to see a review of the Quoddy True Penny, you can check out the review here.
What’s the Best Penny Loafer under $700
- Winner: Alden Leisure Hand Sewn – $517 – $621
- Alden Leisure Hand Sewn Seconds (Shell Cordovan) [Requires Shoemart Log In] – $519
- Allen Edmonds Randolf Shell Cordovan Loafer – $695
- Crockett & Jones Boston – $640
For loafers over $500, expectations are justifiably high. These four 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. If you’re not a fan of that last, or the LHS in general, first quality Allen Edmonds Randolf Shell loafers are available for a bit more, though I don’t think it fits in quite as well as the now-discontinued Patrio. Alternatively, 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) – $830
- Crocket and Jones Harvard – $950
- Edward Green Piccadilly – $1,285
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.