Rather than provide an example of my own shameless salesmanship — which I’m happy to do on a regular basis going forward — I thought I’d expose what is quickly becoming a minor pet peeve of mine: the elusive "shoes that go with jeans and a suit".
To men that don’t like to shop, or to spend money on clothes, the Shoes-That-Go-With-Jeans-and-a-Suit, hereby shortened to STGWJAAS, is the Holy Grail. Rather than having to own two pairs of shoes, you only have to buy one! What could possibly be better than that? Well, nothing, if such a shoe existed. The truth is, with 97.2% of the shoes out there, they are, at best, going to dress down your suit or dress up your jeans, and at worst, break basic rules of fashion. If you’re ok with that, I apologize for wasting your time; if you’re not, punch in the face the next salesperson that tells you the shoes you’re trying on are perfect for jeans and a suit.
Now, forget what I just said as I share with you the couple of pairs of shoes we sell that can make the leap with a list of necessary caveats:
Michael Toschi Caan: I absolutely love this shoe. It’s shape is undoubtedly sleek enough to be a dress shoe, although a Dress Shoe Fundamentalist would argue that a slip-on is not technically dress shoe. More improtantly, the Caan has these subtle bright orange lining details that pretty much require you to have orange in your outfit (a tie would suffice). On the other hand, it is the orange detailing that makes them a really cool pair of shoes to wear with jeans. So to summarize why this is so difficult: these shoes can be worn with a suit, provided you don’t mind a slip-on with some personality that requires you to do something to accentuate the color orange, and you can wear them with jeans provided you’re not wearing them with anything that will clash with the orange.
Michael Toschi Berta: The Berta’s are another versatile shoe with specific, anal-retentive limitations. First, the contrast-stitching on it does "dress-down" a suit. A purist wouldn’t even consider shoes with contrast-stitching as "dress shoes", but for the sake of argument, let’s say we’re willing to overlook that. Conversely, the contrast-stitching is a great detail with a matching belt and a pair of jeans, but the shape of the shoe will still be dressing up your jeans in a way that makes them perfect for the hot, new restaurant, but overdressed for almost any other activity to which you might be wearing jeans.
That’s pretty much it. Out of all of the shoes we sell — which is almost 100 different styles — those are the only two pair that I would attempt to wear with a suit and with a pair of jeans. Every other style fits neatly into the dress shoe category or the casual shoe category. And I’m not afraid to say it.