Recommended: most iconic/best penny loafer money can buy

[comrade]

Thirty years ago I had a pair of what were then considered "classic"
Wildsmith loafers. The were unlined and were made of heavy leather.
I do not find them on the Wildsmith website. Not the same company
which made loafers for King George V.

 

[symphvaria]

Thirty years ago I had a pair of what were then considered "classic"
Wildsmith loafers. The were unlined and were made of heavy leather.
I do not find them on the Wildsmith website. Not the same company
which made loafers for King George V.

Aren’t those just EG Harrows?

 

[James Fanta]

+1 for JM Weston if you want something that works with wool trousers and a blazer or with jeans and an OCBD with rolled-up sleeves. Others are too shiny/dressy or too casual. Weston 180s hit the perfect sweet spot in the middle.

 

[Wolf of Taunusanlage]

JM Weston 180;
Gucci Horsebit 1953;
Alden LHS (986);
Not really iconic but would add EG Piccadilly, CJ Boston and Cavendish as well as Alden Full Strap Loafer.

 

[troika]

My list that I own or have owned

JMW 180
Alden 987
John Lobb Lopez
Gucci Horsebit

 

[Clouseau]

JMW 180 are iconic here in France since the 1960s.

Bass Weejun iconic too but sh*tty quality now.
In the same price category i find Sebago better.

Rancourt ?

 

[Concordia]

Aren’t those just EG Harrows?

Or Eton. Two classic/iconic, if somewhat more delicate models.

For CJ Harvard, consider their slim city rubber sole. Especially if you really are scooting around a hospital all day. If that is not in their shop in the color you want, Ben Silver has some alternatives and you can also go MTO with CJ.

 

[smarley]

Honestly, when it comes to Loafers the fit will be the most important aspect of it overall. If you have critical feet in this regard you will get the most joy and wear out of the pair that fits you best.
Not many people will notice the difference between a JM Weston and an Alden. Maybe some notice the difference between an Alden and an Edward Green. But then again most won't. All people see is a black slipper of some sort anyways.
Regarding this topic I think as soon as you dive deep into the menswear bubble one becomes very conscious of stuff which others will probably never notice or care about. What is paradox about it is the fact that you get more self-concious in what you are wearing, criticizing it even and thus feel worse and less confident which will probably make you look less stylish. But this is getting kinda philosophical now lol

This.

I can’t tell you how many pairs of loafers I have purchased and given to Goodwill because I loved the look, but they didn’t fit my feet.

 

[nabass]

The Bass Weejun with the beef roll is the most iconic but far from the best. Alden LHS is to me the most iconic in color 8 shell or Alden's unique snuff suede, it has a golden wheat shade. I also feel a penny loafer comes in a few different styles but overall is a low profile shoe so if you want something really nice get the Edward Green Duke.

How do the Dukes compare to the Piccadilly?

 

[moltoelegante]

I have these in dark brown. Best loafers I have ever tried but of course there are many others I would still like to try!

Church's Hertford (Custom Grade)

 

[classicoutfits]

Thank you all so much for your advice and suggestions!

I guess I prefer black due to my subjective reasoning that it is more versatile than other colors (burgundy, browns) and I find that black falls in line with my much more conservative and non-flashy personal style. I do realize that may be an erroneous way of thinking...

I am very tall and do wear nice suits/sport coats to work and for whatever reason I feel as though a non-black color would only attract even more attention. My colleagues universally all wear scrubs to work so it does stand out quite a bit when someone wears something different.

I understand where you’re coming from, also work in a healthcare setting, and many colleagues are wearing scrubs to inpatient. I don’t think though that the color of shoe can be flashy unless you’re choosing something extreme. My favorite would be a dar brown suede because it’s subtle versatile and the texture matches with many outfit and suits. But you are 100% right, I don’t know why lot of people in this job setting choose black shoes maybe just a tradition

 

[assberg]

Saint Crispin's, maybe the so called best shoes on earth...

 

[pkincy]

Iconic, but not the Best: Bass Weejuns

History

Shop the home of traditional Penny Loafers and Bass Weejuns, est. 1876. Quality, handcrafted footwear for men & women with FREE UK delivery & returns.

www.ghbass-eu.com

60 years ago when I was in College the Bass weejuns were the only answer, However their quality quickly fell off a cliff and I wouldn't wear them today.

 

[ChicagoStyle]

If money is no object, then do consider John Lobb Lopez or Edward Green Piccadilly. I own the latter, in black grain, and it is a fantastic shoe which is well-made and the skin is of high-quality.
I would also say that not all shoes will fit so do your best to try all the models that you fancy before pulling the trigger.

I love the Cavendish but that is a tassel loafer for a future purchase, perhaps?

If the last fits your foot, I couldn’t agree more with the Lopez and Piccadilly

 

[Club Soda]

How do the Dukes compare to the Piccadilly?

The Duke is a traditional, round toe penny loafer named after the Duke of Windsor. The Piccadilly is what I would call a dress loafer as the stitching is the same as a tassel loafer, the dressier loafer, but has a penny strap instead of tassels. Some dress loafers have an extended strap, a full strap, that extends to the welt, see The Montpelliar.

The Piccadilly and Monetpilliar come on the 184 last which is the same last as the Belgravia and Greenwich, the tassel loafers. The Duke is on its own 137 last. They size the same but fit different. Tassel Loafers are supposed to be more sleek and narrow in the toe box than a penny as they are a "dressier" shoe, so dressier pennies are usually on that same last. The Duke has a little more room in the toe that gives it a comfortable, casual loafer feel.

I recommended the Duke because you asked for most iconic penny loafer. To me, The Duke is an actually penny loafer and among the best in the world that can be bought without bespoke. Any other style of loafer that is considered a penny is a dress loafer to me and is derivative of that style of penny loafer, thus less iconic and alternative in application; a dress loafer is inbetween a tassel and penny and somewhat niche. Both styles of penny serve the same purpose but the iconography of the penny loafer is its intentionally dressed down yet versatile appearance. The penny loafer held the responsibility that canvas deck shoes now hold for quite some time, yet a penny loafer still works with a suit, sport coat, blazer, or jeans and a tee shirt. Edward the VII, Michael Jackson, James Dean, Kennedy, and Bush 41 wore black calf pennies, not dress loafers.