Note: I originally wrote this article for Reddit’s Male Fashion Advice community. Since the information may be useful to this audience as well, I’ve decided to post it here.
In celebration of the good weather we’re having here on the West Coast I thought I’d write a roundup on one of my favorite shoe styles – the penny loafer. This list covers all of my favorite styles, as well as many other options at a variety of price points. To start, here’s an album of some of the shoes mentioned in this post.
A brief history of the penny loafer that you are welcome to skip:
G.H. Bass is generally credited with the development of the classic penny loafer in the mid-30’s (they were called “Weejuns” – short for Norwegians – which is where the style originated). At the time, apparently public phone calls cost about two cents so by loading up your shoes you could call your mom later and tell her that you were going out to the malt shop with the boys. The popularity of the penny loafer reached its peak in the fifties and sixties, when it became synonymous with the post-war “Ivy Look” and with prep culture in general. Since then, it has maintained its association with classic, comfortable, American style.
About this list and how to wear penny loafers:
This list definitely won’t be exhaustive; it will lean a bit to my own tastes. I tend to prefer styles that are a bit chunkier and casual, as opposed to the more elongated and angular Continental styles. In my mind, the penny loafer in its purest form is a casual, preppy shoe, so I gravitate toward brands whose products reflect that. Penny loafers are a natural pairing with chinos, oxford cloth shirts, and other preppy clothing. They’re also great with most denim, especially those that are a bit more broken in. They can sometimes be worn with tailored clothing like trousers, sportcoats, and suits, although this is a bit more of an advanced move.
Just about every prominent footwear brand will have a penny loafer or two, so if you’re loyal to any one brand be sure to see what they have available. Here are some common go-tos:
Under $200: Footwear at this price tends to come with some sacrifices – for starters, you generally won’t get the quality of materials and construction that make great footwear so enjoyable. With that said, there are a few brands worth mentioning.
- Meermin: everyone’s favorite budget shoe brand has a few penny loafers in their arsenal. Personally, these are a touch too sleek and elongated for my tastes but it’s hard to argue at this price. They’re definitely the best buy around $200 in my opinion, and the fact that returns go through their new NYC store now makes them that much more approachable.
- G.H. Bass: these guys have the distinction of having allegedly invented the penny loafer, but outside of that there’s no real reason to get them. Their classic beefroll Weejun looks OK stylistically, but the quality is pretty garbage (I know this because I bought a pair years ago before I knew any better). I’d recommend saving up for something else on this list unless price needs to be in the double digits and buying shoes from dead people’s closets on ebay weirds you out (a phobia I’ve bravely managed to overcome). EDIT: they do have a made in USA collection that may be worth looking at, although my hunch is that they are made by either Rancourt or Quoddy (both on this list).
- Jack Erwin: These folks have three penny styles that all clock in under $200 – again, to me the more angular shape doesn’t do the style justice (and I think Meermin’s quality is notably better), but it’s a solid price point if you want to avoid spending half your rent on a shoe that makes you look like you dropped out of Princeton.
- Beckett Simonon: This brand offers footwear at an impressively low price by keeping no inventory and placing group orders for all their products. They recently released a few loafers in suedes and calfskins. The biggest downside is that these won’t ship until mid-summer, but if you’re not impatient then these could be an affordable buy. Keep an eye out for sale codes, too.
$200-$350: This is where choices start to open up. There are definitely some solid pieces in this bracket.
- Rancourt: these guys have worked to expand their footwear line extensively in the past couple of years, but I think that the handsewn styles are still what they’re best at. They have a bunch of penny styles, and the beefroll and pinch penny are their classic models. These have a bit more of a rustic vibe due to their handsewn construction style. And for under $300, they’re a great choice for a comfy, casual, American-made classic. Quoddy and Oak St. Bootmakers also make loafers in a similiar “Maine handsewn” style, although I tend to prefer Rancourt.
- Loake 1880: the most approachable Northampton brand has an attractive penny style, the Whitehall. Unfortunately, about two years ago Loake changed up their distribution strategy and now it’s much harder to get them in the US (and prices went up around 25% for US customers). If you can score a pair under $300 they’re a great buy, but if not then I’d check out other options.
- Morjas: This young Spanish brand has one penny loafer style. I’ve never handled any products from them but they look pretty promising, especially for the price.
$350 – $600: To me, this is the sweet spot – the best quality and design for your money. I try to save up for shoes in this bracket, even if it means buying used or hunting for sales.
- Allen Edmonds: The more expensive AE gets the harder it is to justify getting them over Alden, but they do have some solid pennies if you want to save about 20% off the Alden price. The Randolph is my favorite, available in various calfskin and shell cordovan colors. And there’s always the AE sales and seconds game if you wanna get them at discount.
- Alden: As one of the most storied American shoe manufacturers, it’s no surprise that Alden has a good number of handsome loafer styles to choose from. My favorite are the unlined suede pennies, which are exceptionally comfortable. The combination of the super soft suede from CF Stead (the preeminent suede tannery) and the flex welt sole make them feel like slippers. My favorite is the dark brown, but all the colors are pretty great. Another excellent penny from Alden is the Leisure Handsewn, often made up in shell cordovan. Hard to go wrong with any of their choices, though – loafers are one of the things that Alden does best.
- Crockett & Jones: In my opinion, one of C&J’s greatest strengths is their collection of more informal shoe styles. They have a few great penny loafer models, but I think the best is the Harvard, no contest. The combination of unlined construction (great for going sockless), classic last shape, and beautiful apron stitching makes them one of my all-time favorites. They’re available in a variety of calfskins, suedes, and shell cordovan from Horween. I have a pair in tan calfskin and they’re the shoes I want to be buried in. For purchasing, it’s much better to go through a UK-based retailer or direct through via a UK store (the US prices are jacked up significantly).
- Carmina: The premium Spanish brand always offers great value for the price, and their loafers are no exception. I prefer the more casual styling of Alden and Crockett & Jones for penny loafers, but if you’re looking for a more European vibe then these are a great choice.
Note: Coincidentally, Brooks Brothers carries shoes made by Allen Edmonds, Alden, and Crockett & Jones – they often aren’t labeled as such, but you can usually tell from the photos. I mention this because it means that you might be able to grab a pair during one of BB’s better annual sales.
Over $600: the world’s your oyster. At this point you should be getting superlative materials and construction, as well as excellent finishing.
- J.M. Weston: I’m told that the 180 loafer is a bit of an icon for the French brand and that they’re a big hit in Japan, but honestly the style doesn’t do that much for me. I’m sure the quality is great, but for $850 I’d rather get a pair of Aldens or C&Js and keep the extra $300. Better luck next time, France.
- John Lobb: The Lopez is one of Lobb’s classic models, although I’ve always been weirded out by the size of the penny-holder part – doesn’t seem like it would be a secure place to store change. Perhaps they’ve been adjusted for inflation to hold quarters instead of pennies, I dunno. Lobb makes exceptional shoes, so if you have money to burn and the style appeals to you then go for it.
- Edward Green: I mean honestly, if you can afford Edward Green then you probably don’t need my advice. The Picadilly model is excellent and quite formal for the penny style – definitely the best on this list for dressing up, if suits with loafers are your vibe. If I were to splurge on a pair of EGs their penny loafers probably wouldn’t be my first choice, although this picture of Hooman Majd’s feet makes me reconsider.
TLDR: Rancourt, Loake or Meermin would be my go-to in the lower price brackets, both Alden and C&J crush in the middle, and if you really want to spend a grand on penny loafers then you can do whatever you want because you probably don’t care about my opinion to begin with.
