That Guy…

That Guy…


Yesterday afternoon I decided it was time to get a fresh shine to my black cap toes.  I knew I could not rest until it was done, so I went to my local shoe shine to quell my anxiety.  Typically I like to observe what the shiner is doing, to see if their are doing a proper job.  However, this time I could not get my mind off of what the gentleman before me was wearing and the shoes he was getting shined.  This guy was wearing a black suit with slip on dress shoes, an abomination on two fronts.  For one should not wear either item as professional dress, let alone the two together; but sometimes when it rains it pours.

In my view, almost as bad as square toed shoes are slip on dress shoes like the ones the man was wearing and like pictured below,

Horrible shoes: Stacy Adams

Shoes like this have no real place in a proper wardrobe, for a variety of reasons which I will not get into right now.  They especially do not have a place to be worn with a suit.  Nor do they have a place at a shoe shine stand.  At best, they have a place in one’s trash can (so if you have a pair I suggest you dispose of them via the closest trash receptacle, homeless person or better yet with those poorly dressed protesters at Occupy Wall Street).  Most well dressed men will tell you that you can tell how well a man dresses by looking at his shoes (women also take note of your shoes, trust me).  Don’t let yourself be ‘that guy’ that I saw.  By looking at his shoes I could tell he was a terrible dresser.  I was right, things only got worse for him…


  1. Hi Justin. I’ve recently discovered your blog and I have enjoyed reading all the posts.

    In your What I Wear Part X, you sport your Indochino suit with blue suede slip ons. Did you feel that was an appropriate combo with your suit given your rule no. 15?

    What is it with suits and slip ons that is such a no-no anyway? I’ve seen a lot of great outfits in Europe (esp Italian guys) pairing suits and slips ons and I thought they looked great. Just wondering your thinking on this one.


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  3. A couple of notes
    1. I did see that you were wearing slip-on shoes in your dragon inside review. I think they were burgundy slip-ons, but they were not squared toes like the ones pictured above.
    2. The slip-on shoes have become a lot more popular since 9/11 and the stringent security requirements at the airport. They’re easy to slip off and on for quicker pass through the TSA check points.
    3. For Asians, such as myself, we take off our shoes at home, and again, quick ability to slip shoes on and off definitely helps.

    Lastly, I prefer slip-ons that look more like the Derby shoes.

    • JC,
      Valid points. Upon re-reading the article I realized that I did not specify enough about the offending shoes. Slip on shoes are fine, but it is the slip one with the elastic side gusset that I cannot stand. Like the Stacy Adam shoes pictured.