A Guide to Men’s Loafers

May 11th, 2015

It’s officially loafer season, so I thought it would be a good time to brush up on our loafer vocabulary.

Here are the classic loafer shapes/styles that have defined timeless leisure in menswear over the past hundred years or so. Keep in mind that many modern designs are simply hybrids of these tried and tested styles, taking classic design elements and mashing them up into a “new” modern shoe.

The Penny Loafer


Olive Trousers by Articles of Style

This is a classic casual loafer for men, based off the original Bass Weejun design. They’re a great match for chinos, jeans, cords, or just about any other casual trouser. The signature design details are the rounded moc toe, the “beefroll” bindings on the sides of the vamp, and the diamond-shaped slit which has been known as a clever place to store actual pennies.

The tradition of carrying coins in penny loafer has uncertain beginnings. One explanation is when American prep school students in the 1950s, wishing to make a fashion statement, took to inserting a penny into the diamond-shaped slit on their Weejuns. Another theory is that two pennies could be slipped into the slit, enough money to make an emergency phone call in the 1930s. Either way, the name penny loafer came to be applied to this style of slip-on and has since stuck.

The Horsebit Loafer


Gray Lambswool Tweed Trousers by Articles of Style

In 1966, Italian designer Gucci saw the popularity of the penny loafer and adapted it with a metal strap across the front in the shape of a horse’s snaffle bit. These Gucci loafers (now a general term referring to shoes of this style by any manufacturer) also spread over the Atlantic and were worn by 1970s businessmen, becoming almost a Wall Street uniform, reaching widespread use by the 1980s.

The Tassel Loafer


Mid Gray Flannel Trousers by Articles of Style

Traditionally the tassel loafer is a wholecut style with a rounded toe outlined by a reverse seam. The leather “stings” that hold the tassels usually outline the back heal of the shoe – a detail that is similar to boat shoes like Sperry or Sebago. These loafers are often made of stiff oxblood leather (preferably true cordovan) and have been known for their durability, versatility, and timelessness. For this reason, they are a great loafer to search for in vintage and thrift shops.

The Double Monkstrap


I don’t have to say much about this shoe, as it has become the defacto shoe for menswear enthusiasts…to prove their menswear enthusiasm, especially within the realm of blogs and online communities. Although it’s becoming more and more “expected” by the day, it’s still a good-looking shoe with a versatile mix of dressy and casual – which is why it became popular in the first place.

The Single Monkstrap


Essential Charcoal Trousers by Articles of Style

Not nearly as popular right now as its double-strapped cousin, the single monk is one of those styles that is rarely seen in menswear. Monkstraps come in a wide variety of designs as the hardware (buckles and straps) come in many sizes, shapes, metals, etc. The toe is also plain and open for design interpretation, allowing for details like captoes, wingtips, medallion perforations, etc.

The Kilted Loafer


A little dandy, a little retro. This is one of those old man styles that can be very “Granpa Chic”. Typically a kilted loafer has a low vamp which makes them easy to slide on and off. In some cases the “kilt” is also removable, and held on by mocassin-like leather strings (similar to the tassel loafer “laces”). In my opinion these are going to be the next loafers to trend in menswear (like the dub monk), as things gradually become a little more “relaxed dandy”.

The Driving Shoe


Khaki Cotton Trousers by Articles of Style

These slip-ons are designed for driving, not walking. They are usually softly constructed from a supple leather or suede, which is meant to be worn comfortably without socks. They usually have flat bottoms with grippy rubber “grommets” (as pioneered by Tods) rather than heeled soles that could get caught on the edge of the pedals.

The Formal Pump


A formal loafer (or slipper) is black, understated, made of shiny patent leather, and has a low vamp (some black hosiery will show, so make sure to wear the right formal socks). They also sometimes have a simple bow detail on the front, often made of grosgrain to match the trims of the tuxedo. These should be kept shined and reserved for formal occasions.

The Slipper


The velvet slipper was originally designed as a modern alternative to the formal pump above. The vamp is a little higher, but the design is still very minimal. Over the years men have adapted them (in all kinds of fabrics from canvassy linen to needlepoint cotton) by adding their own emblems/crests/monograms, and wearing them with everything from leisure suits to jeans. It’s an in-your-face style that is usually worn to convey a subtle F-You to conformism.

The Boat Shoe


Your best bet is you’ll be close to the water, or expecting rain. Boat shoes (also known as deck shoes) are typically canvas or leather with non-marking rubber soles designed for use on a boat. A siping pattern is cut into the soles to provide grip on a wet deck; the leather construction, along with application of oil, is designed to repel water; and the stitching is highly durable. Modern boat shoes were invented in 1935 by Paul A. Sperry of New Haven, Connecticut after noticing his dog’s ability to run easily over ice without slipping.

The Espadrille


These simple casual summer shoes have been made in Pyrennean Catalonia (Spain) since the 14th century at least, and there are shops in Spain still in existence that have been making espadrilles for over a century. The oldest, most primitive form of espadrilles dates as far back as 4000 years ago. Traditional espadrilles have a canvas upper (although they came in just about every fabric from cotton to suede) with the toe and vamp cut in one piece and seamed to the jute rope sole at the sides.

Hybrid Designs

As I mentioned above, modern loafers are often designed by combining elements of the classic styles outlined above. There are countless combinations. For example…

The Kilted Monk


The Tassel Driver


The Wingtip Monk


The Tassel Slipper


There will always be new iterations of these classic designs coming out…I’m just hoping that this guide can provide a base vocabulary to operate from when discussing the vast world of men’s loafers.


Thanks, as always, for reading. If you have any questions about our online custom menswear, feel free to contact us anytime. We look forward to serving as your personal tailor and stylist. 

Yours in style,

Dan Trepanier

Photography by Alex Crawford.

  • Christopher Jordan

    Will I look like a fool if I wear loafers in the winter?

  • Kyler

    I have to know where those first socks are from in the penny loafer photo

    • TO

      Smart Turnout (Google em)

  • Kevin Ogario

    Hi Sir,

    I have a question does this
    GOLD CUP KENNEBUNK ASV 1-EYE LOAFER looks good also in shorts? how about jeans and uniform? since no idea about this stuff… trying to change :D


  • Matt Foster

    Does anyone know where i could get a pair of the Tasell Slipper style as shown?

  • http://www.GetFoundMarketing.org/ David Scarpitta

    Loafers, loafers, loafers. It actually makes my head hurt on “Which ones are which”. In fact I was confused when I had seen all of these at https://www.menssuithabit.com/shoes/mens-loafers.html which classifies some as “driving shoes”, and “slip ons”. This kinda really breaks it down for me, but honestly it’s still a little confusing.,lol

  • randOh

    Does anyone know where I can get something like the “Tassel Driver” shoes?

  • Stuart

    For those of you interested in picking up a pair of custom slippers, check out Charles Philip. They’re a Milan/Shanghai company that makes damn cool shoes.


  • TO

    The article’s display picture is just beautiful. I was confused for a bit about the monkstraps making the list, but then I realized you basically slip them on so it makes sense. The way my mind works, I have a deep appreciation for categorizing and listing different types of things, so I am gleeful on the inside to see this seasonal footwear article added to the awesome growing section of guides!

  • Owen

    Hey Dan, what’s your opinion on wearing tassel loafers with jeans? yes or no?

  • Miguel

    My favorites are the Double Monks, Tassel Loafer and the Slippers, of course like Dan said, nowadays you’ll find combinations of all this shoes, like a cap toe D Monks, Swede Loafers Slippers.

    Excellent article, always love how you bring some history into this type of articles Dan.

    By the way, what brand are the Wingtips Monks? thanks.

  • James Wong

    Dan/AoS readers, I bought these Ralph Lauren Penny Drivers brand new for £100 off eBay for my four months of travelling Asia. They were great (easy to slip off for airport, lightweight, smart) however I noticed it lost shape due to my little toe pushing outwards (see pic). Is this due to the shoes being too small, maybe I walk strange or do I need to buy wider shoes?

    • cam

      they could be too narrow. do you use shoe trees to help maintain their shape? if not, i would invest in some.

      • James Wong

        Thanks for the reply Cam. Do menswear shoes often come in different widths? Like I said, I was backpacking for four months so carrying shoe trees wasn’t the on highest of my priorities :p however, even if I did shoe tree them, they are still out of shape when wearing them. I’ll tree them for a bit and see if it helps.

        • cam

          different widths? absolutely

        • http://www.TSBmen.com/ Dan Trepanier

          Yup. The width is denoted by the letter.
          Very Narrow: AA
          Narrow: A, B, C
          Regular: D (or M or “Medium)
          Wide: E
          Very Wide: EE, EEE

    • http://www.TSBmen.com/ Dan Trepanier

      Looks like your feet are short and wide, and the loafers are narrow and long. You’re probably something like a 9.5E, but wearing something like a 10C…

      • James Wong

        Haha, thanks for the reply Dan, though I don’t hugely appreciate being told I have hobbit feet!

        I actually had a look at the inside of the shoes and amazingly they are marked as a 9E which is wide! I checked my Frye’s and they’re only a D and fit fine. However, I am usually a US 9.5 which probably is the issue…

  • Harrison Krupnick

    Really like the penny! What brand and model is it?

    • Herb

      Bass Weejun x Barneys. I checked out the Style Guide and figured I’d answer for you since this blog has completely lost its personal touch and the team no longer responds to comments like it used to.

      • http://www.TSBmen.com/ Dan Trepanier

        Good thing we designed a brilliant Style Guide! This is exactly how we were hoping it would work.

        Apologies for the delayed responses…we’re doing some heavy lifting behind-the-scenes to bring you something MAJOR that I think all of you guys are going to appreciate!

        Stay tuned…

    • http://www.TSBmen.com/ Dan Trepanier

      Hey Harrison! The penny loafers are by Bass Weejun x Barneys

  • cam

    no boat shoes, camp mocs or espadrilles???

    • http://www.TSBmen.com/ Dan Trepanier

      Updated just for you, player. Cam got the power.

      • cam

        perks of being an OG…haha

      • James Wong

        glad I re-read the comments – I would have missed the add ons!

  • Vape

    Question for anyone. I tend to only where shoes that require socks specifically for the reason that wearing no socks enough times becomes a little gross and/or uncomfortable. Your feet naturally sweat all day, and if it’s hot, they can get very sweaty. Combine that with wear and tear and it can feel like putting on used gym clothes

    Has anyone else had the same issue? Do you wash your shoes? Use powder?

    • cam

      no show loafer socks will change your life

      • http://ledebonnaire.tumblr.com/ Juan Zara

        That, linen socks (although they tend to run pretty expensive) and talc spray for feet for when going sockless is extremely necessary.

    • James Wong

      Agreed with the no show socks. These are super popular in Asia and can be bought in most shops. I found in the uk though, they can still be bought in Aldo and Uniqlo so go check those shops out.

      • AdamE

        Has anyone found no show socks that actually stay in place? I bought some, but they slide down and make you 50% sockless and 100% less comfortable.

        I do sockless in some of my shoes, and I do use powder regularly (I keep a small thing of powder in my office too, if I feel humidity or the slightest inkling of smell, I’ll hit them again mid-day…) to keep dry, and then cedar shoe trees between wears.

        • James Wong

          All my no shows socks have stayed in place – maybe try a different brand?

        • donpelayo

          I can recommend the no show socks from Falke. It’s a well known German brand and easy to find in Europe or the US

    • Harrison Y.

      Uniqlo has an affordable no show sock. There is a company by the name of Taft that I ran across recently that has some fun colors & patterns.

    • Papi Moscow

      I used to feel same way a couple of years back. Until I started this simple system:
      -I put foot powder inside of shoe so the feet stay dry. After a day of wear, I clean out any powder residue with a damp cloth (just water).
      -Then I let them air dry empty for the next day.
      -Then on 3rd day I put back in cedar shoe trees.
      So if you want to go sockless all week you need at least 3 separate pairs of shoes.
      Been doing this for about 5 years now & no problems with odor, damages to shoes or to my feet.

blog comments powered by Disqus

NYE: “Black Tie Creative”

A Simple Guide to Pattern-Mixing

The Dandiest Tailor in London feat. Joshua Kane

“A Look Only I Can Wear” feat. Maor Cohen

The Odd Vest