A Summertime Favorite: Penny Loafers

Once the weather warms up and the days get long, I often find that the best shoes are either sneakers or slip-ons. I typically wear sneakers with jeans and casual outerwear, and slip-ons with dressier trousers and sport coats. Styles can really range, but most of the time, sneakers tend to be white and minimalistic, and the slip-ons tend to be penny loafers.

The penny loafer is often thought of as a quintessentially American shoe – a style that’s most at home with tweed jackets and Shetland sweaters, as they were originally worn on Ivy League campuses in the mid-20th century. Today, however, you can safely wear them without any preppy connotations (although, you can also wear them as such, if you wish). With a sleeker pair of European pennies, for example, you can combine them with a soft-shouldered sport coat, wool trousers, and an open collared shirt for a very dégagé Continental look. With some beefroll loafers, jeans, and a light jacket, you can go back to looking like an American, but in a way that doesn’t feel too preppy. 

If you haven’t yet got yourself a pair, consider some of these:

  • Highly expensive at $750+: JM Weston’s 180 moccasin and John Lobb’s Lopez are pretty iconic, with the first having uniquely high walls around the toe that help distinguish it from the pack. My favorite loafers in this price tier, however, are all from Edward Green – an English firm known for its tasteful designs, quality construction, and beautiful finishing. Check out the Piccadilly, Montpellier, Sandown, and Harrow to start.
  • Pricey options between $350 and $500: Less expensive, but no less well-made, are loafers from all of your usual suspects. Carmina, for example, has something that looks very much like Edward Green’s Montpellier, while Alden has a wide range of handsome American designs. More recently, Wildsmith (a bespoke shoemaker once famous for their unlined loafers) relaunched as a ready-to-wear brand, and although their loafers aren’t as close to their originals as Edward Green’s Harrow, they’re priced competitively. Shipton & Heneage will also have a nice range of options, and they’re made a bit more affordable through the company’s Discount Club. Additionally, Crockett & Jones is very much worth a look, as are Alfred Sargent, Sid Mashburn’s house line, Kent Wang’s antique calf loafers, and the newly launched Paul Evans.
  • A bit more affordable at $350 and below: Of course, for more affordable shoes, there’s always Allen Edmonds’ factory second store, where the company heavily discounts shoes that didn’t pass quality control. Flaws are often very, very minor, if even visible at all. Loake’s 1880 line is also worth a look, and they sometimes produce for Charles Tyrwhitt and Herring (just note that some Loake-made shoes aren’t of terribly good quality, so use good judgment). Similarly, Ralph Lauren and Brooks Brothers will have some nice models, even though their quality can really range. Stick to the stuff that retails for $350 and above, and wait for end-of-season sales. In addition, Meermin offers some of the best price-to-value ratio right now in footwear, especially once you take into consideration their made-to-order program, and Jack Erwin is the best I’ve seen in the sub-$200 price range. For more American styled loafers, check out Rancourt and Bass’ Made in Maine collection.
  • Shell cordovan: Lastly, shell cordovan loafers are worth highlighting. Although shell cordovan is traditionally a workboot material, it works wonderfully today for slightly dressier styles (think wingtips, tassel loafers, and penny loafers). Alden’s Leisure Handsewn is a really beautiful American model, while Carmina will be more European. Meermin may also be able to make you something through their made-to-order program.

(Pictured above: Hooman Majd in his fifteen year old Edward Greens)

The Wonderful Split Toe

If I had to stick to one style of footwear for the rest of my life, it might have to be the split toe. Defined by that vertical toe seam and crescent apron, the style is sometimes referred to as an Algonquin in the US and a Norwegian in Europe. The terms here can be confusing since “Norwegian” can also refer to a method of attaching a shoe’s uppers to its sole, but not all Norwegian shoes are made with Norwegian constructions. (I suppose this means a “split-toe trifecta” might be a Norwegian made by a Norwegian using a Norwegian construction, but I don’t know any Norwegian shoemakers).

In any case, the nice thing about split toes is that they’re less formal than oxfords and less ubiquitous than wingtips. I find they go with everything – business and casual suits, sport coats and trousers, and (sometimes) even certain styles of casualwear. Everything is in the details, really. Like with any style, the sleeker the shape, the more refined or “city” they become; the chunkier the style, the more causal or rustic they look. For the most part, I find most good split toes can be worn without much thought, making them an easy go-to when you’re running out the door. See our friends Bruce Boyer, Ethan Newton, and MostExerent for style inspiration. 

Unfortunately, split toes tend to be expensive. Although there are plenty of beautiful examples with machine-stitched aprons, most are good split toes are handsewn around the toe (which adds time and money). If you’re looking for a pair, here are some options.

Under $350

As usual, your best bet is eBay and thrift stores, where you can find gently-used models from well-regarded makers. I find Brooks Brothers and Ralph Lauren to be particularly good for value, as they’ll often just rebrand high-end shoes with little to no change in quality. Just look for the ones that have been made in the US or UK. 

There’s also Meermin, who used to produce a model with a “pie crust” apron – a detail that some people pay upwards of $1,500 for (theirs is executed surprisingly well). It doesn’t seem to be in production at the moment, but with enough emails, maybe they’ll bring it back. 

From $350 to $1,000

This is where your options really open up. See Alden and Carmina if you want something with chunkier stitching. That kind of detailing can make a split-toe more casual, although Carmina is still sleek enough to feel relatively dressy. 

There’s also Brooks Brothers, Vass, and Crockett & Jones. The last has them in two models – the Durham and Cornhill. I find the latter more handsome, but the first is easier to wear with either jeans or wool trousers. 

Skoaktiebolaget is also holding a group-made-to-order run this week with Enzo Bonafe, a small Italian producer of handwelted shoes. (Note: Enzo Bonafe’s prices are going up next month, but these are being offered at pre-hike prices). That mid-brown calf looks gorgeous. 

Above $1,000

For the serious splurge, see Gaziano & Girling, JM Weston, and Saint Crispin’s. Or my favorite model of all time: Edward Green’s Dover in dark oak. Excruciatingly expensive, but also exceedingly handsome. You can see an example of the Dovers in the image above. 

Interestingly, the vertical toe seam you see on split toes was once used on wholecut derbies in order to create a more water-resistant shoe (specifically those worn by canal and railway workers in Britain, who didn’t want water seeping into their footwear). Bespoke shoemaker Nicholas Templeman recently posted a story about it on StyleForum. Of course, today, they’re more of a decorative detail than anything, although John Lobb in London still sells bespoke shoes inspired by those original workwear designs.

(photo by Gezzasmenswear)

JM Westion x Maison Kitsuné - The New Yorker J.M. Weston accompanies Maison Kitsuné to New York and creates “THE NEW YORKER” ! Ever since their first collaboration a few years ago, Michel Perry and Masaya Kuroki have known that they share the same vision of style : elegance with a touch of nonchalance.The artistic director of J.M. Weston decided to support Maison Kitsuné’s debut in New York by designing a specific loafer. Michel Perry and Masaya Kuroki worked on the French shoemaker’s emblematic model, the Loafer 180. “New Yorker” Loafer J.M. Weston x Maison Kitsuné sold exclusively from April 19th at Maison Kitsuné at NoMad – New York (1170 Broadway) and at J.M. Weston (600 Madison Avenue).