The Pointy Versus The Square » Manolo for the Men


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The Pointy Versus The Square

By Manolo

Manolo says, one of the Manolo’s many internet friends has left the interesting comment.

Manolo, this seems like a good time to request your thoughts on the square-to-pointy ratio of men’s shoes. I have very squared off toes and have formed a dependency upon the round-to-square toed, plain front black lace-ups that Kenneth Cole manages to make every year. Furthermore, I definitely don’t like the high-fashion, very pointy shoes of the last year or so, and am depressed by the thought that the pointy shoes are back. Does the successful man of the world have to wear the pointier of the shoes? (I’m ambivalent about even the otherwise quite handsmome J&M captoes you highlight…)

Manolo says, for the shoes of the man of the business, the Manolo he prefers the rounded toe shoes, above both the pointy toed shoes and the shoes with the square toes. The reason for this is that in the matter of the business attire, the well-dressed man he should keep to the golden mean.

The attire for the place of business it should not be fashion forward, but rather of the classic nature. It should be distinguished by the high quality of the tailoring and the material rather than the trendiness. A best suits made by the best of the tailors should last you forever, it should never go out of the style.

Much of the same it can be said for the shoes of the man. The best quality mens shoes of the classic shapes will never go out of the style.

Manolo says, if you are serious about the business success, avoid the trendiest of the styles in the shoes and the clothes. It is the sad fact that the man of business he must avoid being made sport of, and so the clothes he wears, they must conform.

There is, however, some of the exceptions to this. If the man he is working in the more artistic field–the architect for the example– he is granted some laxity with regards to the attire. He is somewhat freer to follow the whims of the fashion.

The final answer to your question is that you are right to avoid the shoes with toes that are too pointy. But also avoid any shoe that is too “fashionable”. The classic, that should be your goal.








One Response to “The Pointy Versus The Square”




  1. Urocyon Says:

    Square toes belong on biker boots. Pointy toes are befitting Austin Powers, guys with big hair and makeup back in the ’80s when it was cool, and wicked witches of the west.

    That’s not to say there’s anything wrong with any of the above if such is your desire, but something to keep in mind when choosing. At least, such is my humble opinion.

    -urocyon
    Who did indeed have big hair in the ’80s, but had the prescience to avoid photographic evidence thereof. ;)










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