Penny Loafers - Classic Round Toe or Modern Elongated Toe?
Loafers by Crockett & Jones

The penny loafer is the most classic style of loafer there is. And probably my least favorite as I personally prefer a butterfly or wholecut version. But I am not the end all be all as most of the world still loves a good ‘ol fashioned Penny strap version.

But the question now is which version is more preferred by the people: the classic round last or the modern elongated toe? I have always preferred a loafer to be on a round toe. Not an overly round one, but a smart round one that has some shape other than just “round.” But now you are seeing a lot of loafers on the chisel last, such as Crockett & Jones’ version above. It is definitely an elegant option and for me makes it more dressy for suit attire. But the flip side IMHO is that it makes it almost too slick for jeans whereas the round last keeps it more casual, not 100% ideal for suits but good for casual wear.

Whats your take on it? Which do you prefer?

Penny Loafers - Classic Round Toe or Modern Elongated Toe?
Loafers by Lof & Tung
Penny Loafers - Classic Round Toe or Modern Elongated Toe?
Loafers by Edward Green for Unipair

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4 thoughts on “Penny Loafers – Classic Round Toe or Modern Elongated Toe?”

  1. STEPHEN and SARA WIERHAKE

    I like both – and have both styles. I suppose I consider the classic round style more “preppy”, and would wear clothes in keeping with that style. My elongated toe penny loafers look better with more dressy clothes, in my opinion.

  2. I have to say I prefer the sleeker penny loafers such as the C&J example shown above. If it’s in a material such as suede I find it combines both an elegant and casual look.

  3. I have to say I prefer the sleeker penny loafers such as the C&J example shown above. If it’s in a material such as suede I find it combines both an elegant and casual look.

  4. I have to say I prefer the more rounded look in the tassel dino loafer from Nettelton. It has a classic look that works well with slacks, jeans and chinos without being needy or overbearing. Get a chocolate brown pair for starters.

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