The Gentleman: Style Sins

The Square Toed Shoe

This week, The Gentleman was supposed to give you a peek into his end-of-summer party, however, real life intervened and the party had to be pushed back. Instead, I look forward to sharing New Orleans’ end-of-summer styles with you next week.

Today, I bring you the eagerly awaited second installment in my recurring “Style Sins” column. Let’s dive right in to discuss a particular pet peeve of mine, the Square Toed Shoe. Appropriate shoes are so essential to style that I devoted my very first Gentleman column to them. It seems that hordes of men ruin otherwise excellent outfits with poorly chosen footwear. I suspect that a lot of this has to do with skimping on shoe purchases. Men seem at ease with shelling out a decent amount of money for a suit or a shirt, but then are aghast at having to approach $100 or more for a pair of shoes when it is quite likely that they will wear their dress shoes far more often than any other part of their business wardrobe. It’s paradoxical why men won’t invest in higher quality footwear.

Another possible reason for so many ugly shoes pounding the pavement of major cities is a simple lack of understanding about what makes a shoe aesthetically pleasing. The easiest way to avoid wearing a bad pair of shoes is to ban the horrid Square Toed Shoe from your closet entirely. Below is a perfect example of an ugly Square Toed Shoe. It’s the “Run For Cover” by Kenneth Cole, which is an appropriate name considering that a Gentleman should run for cover if he ever encounters this shoe at a department store.

Photo Credit: Kenneth Cole

Unlike a lot of other advice I give on Cubicle Chic, I can’t exactly say why I think Square Toed Shoes look bad. They just do. Maybe it’s the fact that the human foot is naturally rounded and a Square Toed Shoe gives it an artificial angularity. Whatever it is about them, I think they instantly ruin any outfit.

Square Toed Shoes seem to be even more of a menace when men wear loafers. Nearly every loafer I see young gentlemen my age wearing are of the square toed variety. It does NOT suddenly become acceptable to throw style to the wind when you dress down and wear a loafer.

Photo Credit: Kenneth Cole

I save the in-depth discussion of loafers for a later post because they are the ideal shoe to wear in autumn, but for the moment, a horribly angular loafer by Kenneth Cole, the “Ring n Run,” is pictured above. Why is it that all of their bad shoes use the word “run” in the title? To show that I don’t hate exclusively (though frequently) on Kenneth Cole, below is an equally dreadful Square Toed Shoe from Johnston & Murphy. I’ve praised this company before for selling generally high quality shoes, but this shoe, their “Dobson Moc Toe,” is as ugly as both of the previous shoes.

Photo Credit: Johnston & Murphy

The alternative to buying a Square Toed Shoe is to buy a traditional, rounded dress shoe. Johnston & Murphy’s “Melton,” which I wrote about in my very first post, is an excellent example of a classic round “cap toe.” A classically designed shoe like this is not more expensive than the ugly ones discussed above.

Photo Credit: Johnston & Murphy

I’d love to hear more about your thoughts on this “Style Sin.” Are Square Toed Shoes just a personal pet peeve of mine or are they a serious style sin? Feel free to sound off in the comments!

Next time, the Gentleman will be sharing his end-of-summer house warming party and the styles that his guests wear…



Filed under The Gentleman

7 responses to “The Gentleman: Style Sins

  1. Absolutely dreadful! They are so clunky, and for some reason any man wearing square toed shoes wears them for years until they are beyond acceptable for any type of shoe.


  2. Alice

    The square-toed shoes remind me of those shoes Charlie Chaplin (I think) had with the extensions on them so he could lean forward.
    That being said, I really dislike square-toed shoes.

  3. The Gentleman

    Glad to hear that I’m not the only one who finds them to be so ugly! I’m about ready to make a major shoe purchase in a few weeks that I think you guys will like. Stay tuned…

  4. Sara

    You know you didn’t post the style that I SWEAR every man’s mother buys with him when he’s too young to have a serious girlfriend… the square toe with the really distinct seam along it and the really clunky bottom/heel. HORRIBLE! haha

  5. Sandy

    They are also ungodly uncomfortable. They can ruin your feet! I had some I wore for high school graduation and I still regret it – many, many years later. Unfortunately there are photos…

  6. Pingback: Chic Squared Party

  7. Pingback: The Gentleman: Suiting Up « Cubicle Chic

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