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Recommended: most iconic/best penny loafer money can buy

SilverJag

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Gentlemen,

I am wanting to purchase a pair of black penny loafers (money is no object) and wanting to get the most iconic piece available on the market. I humbly ask you experts because I have not kept up with what brands are worth the money. I am looking only at ready to wear models, not bespoke or custom made.

I will be wearing mostly to work (clinic setting) wearing either a suit or most commonly sport coat and wool or cotton trousers. I am leaning towards black for the versatility and more importantly for an under the radar look (I work in healthcare)

I am looking at Alden, C&J handmade (not sure Harvard v Boston v Crawford), etc.

Any tips and advice is greatly appreciated

Regards,
 

Satmoche

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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?
 

SilverJag

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Thank you kindly
I did a deep dive on this model and it really is gorgeous. Thank you for highlighting it. Will likely be the pair I purchase.
 

PurplePolo

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Gentlemen,

I am wanting to purchase a pair of black penny loafers (money is no object) and wanting to get the most iconic piece available on the market. I humbly ask you experts because I have not kept up with what brands are worth the money. I am looking only at ready to wear models, not bespoke or custom made.

I will be wearing mostly to work (clinic setting) wearing either a suit or most commonly sport coat and wool or cotton trousers. I am leaning towards black for the versatility and more importantly for an under the radar look (I work in healthcare)

I am looking at Alden, C&J handmade (not sure Harvard v Boston v Crawford), etc.

Any tips and advice is greatly appreciated

Regards,
Realistically black will be difficult to pair well with cotton trousers, but if you must, I would look at either the JM Weston 180 or the Alden 987, as they strike a good balance between formal and casual.

I think the Piccadilly from EG would be far too formal for cotton trousers, even in pebble grain.

I will caveat this by saying that you’ll need to make sure that the last actually feels comfortable for you.

I went through a similar exercise last year wanting to buy either the Alden 986 (No. 8 cordovan) or a JM Weston 180 and found that neither really fit my feet, which are spade shaped with a high-instep.

In the end I went with the C&J Harvard in brown cordovan, which fit my feet great and are “versatile” but I feel are rarely optimal.
 

JohnnyLaw

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I have the C&J Boston in dark brown pebble grain and I think it's a great shoe for almost any outfit more casual than a business suit.
 

Steve Smith

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Do you have the same shoe in #8? If not, consider that color, much more versatile. There are several great choices already mentioned, and I think that buyers make a choice and then bond to that particular model. I have a pair of Alden for Brooks Brothers LHS in #8 and consider that to be the ultimate loafer, but I wouldn't argue that they are superior to a pair of C&J, Lobbs, etc.
 

SailingIvy

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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
 

dh797_sfs

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aubercy-lupin3565-coinloafer-dupuyvitello-loafer-nero-2022-altoediritto-nagoya-2022827.jpg

French shoemaker Aubercy's Lupin is a great choice -- with the charm point being the strap which looks like a mask, instead of a single penny slot.
 

SilverJag

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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.
 

symphvaria

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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.
Burgundy and dark browns are absolutely considered more versatile than black in classic menswear, and I can assure you that no one will bat an eye at the color of your shoes anymore so than they would at you wearing tailoring in the year of our Lord 2025.
 

comrade

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Iconic, but not the Best: Bass Weejuns

 

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