If the shoe fits

When you like something or get used to doing something the same way over a span of years, sometimes it can be hard to change things up.

I’ve noticed lately that I have that problem with shoes. For example, I wrote recently that I went out on a limb and bought myself a pair of Blucher moccasins from my youth. When it comes to work shoes though I find that I stick with the tried-and-true.

When I was a kid, my dad loved penny loafers. I’m sure he loved them because they came out of the fifties when he was growing up. Back in the day it was fashionable to keep a dime in the half moon cut out slot of the leather strip. This eventually gave the shoes their colloquial name of penny loafer.

I’m sure he liked them too because they represented an easier life than the scuffed steel-toed work boots that he wore to work when he was still physically able. My father had heart problems and he bought me my first pair after visiting the PX in the Veteran’s Hospital where he went. My father couldn’t be happier when he gave me the shoes. I, on the other hand, wasn’t sold on the shoes.

In time though, the shoes grew on me and soon became my go-to business casual loafers. I have a nice pair of black formal wingtips that I wear when I have to wear a suit and tie, but when I need a pair that are a little less formal, but still very presentable I find that I fall back on burgundy colored penny loafers. I try my hardest, but, like clockwork, I come back to what I know.

In particular, I love that I know what they go with and what they don’t. The problem, however, is that it’s not the 60s, 70s, or 80s for that matter. I need to update my wardrobe.

So I’ve been trying to branch out. I’ve been perusing the different types of shoes. It’s slow progress, but I think I’m heading in the right direction. When I went shopping this weekend, I bought a new pair of penny loafers, but hey, I switched colors, buying a pair of black instead of burgundy loafers.

Yes, yes, it’s still the same type of shoe, but progress is still progress. Give me time and maybe in another ten years I’ll move onto suede lace-ups or Chelsea boots or even a double-strap monk shoe.

We’ll see.