Looking Back, You’ll Wish You Dressed Up

Looking back at pictures from the 30’s-mid 60’s, everyone looks cool. No matter what your personal style is, you can’t deny that even the average Joe from these decades looked like a total boss. Ties, fedoras, and jackets abound and everyone seemed to have an innate sense of easy, relaxed style.

When I’ve dug up old pictures of my grandparents, or my wife’s grandparents, if they weren’t completely decked out, they at least looked like they put in some serious effort for the picture. My mother used to say that my dad’s parents were always “well turned out”. It made me think about what future generations will think about me when they see my old photos.

As I look through pictures of me from years ago, there is one constant thought that keeps flickering across my mind: I wish I had dressed up! Now, in the years since I’ve developed enough sense to dress appropriately for various occasions, but prior to that, I really had no idea what I was doing. Growing up, since my dad wasn’t around too much and we rarely visited extended family, I was never instructed from a young age how to dress appropriately. I had to figure it all out myself in young adulthood. That means there were plenty of instances throughout my 20s (and earlier) where I look like a bit of a goofball (or specifically: a child) because I hadn’t taken the extra steps to dress up a little. I’ll give you two specific examples:

I was around 17 or 18 years old at the time. My family travelled to upstate New York to have dinner with my aunt, uncle, and cousin whom we saw once every few years. I remember the dinner taking place in a nice hotel restaurant. The meal was lovely. The company was even better. What do you think I wore for this special occasion? If you guessed something like “chinos/button down shirt/loafers”, I appreciate your optimism, but you’d be way off the mark. If you guessed “ripped jeans/Ozzy Osbourne t-shirt with the word ‘HELL’ blazoned across the front” you would be, regrettably, correct. It wasn’t like I was some rebellious hoodlum, though! It was just a shirt I liked and I had no sense of what was or was not appropriate or respectful. It was a wonderful evening but I cringe every time I see the photos.

This next example was about ten years later. I was about 27 when my wife (we weren’t married then) got her Masters. What did I wear to her graduation? Well, to my credit, I at least put on a pair of chinos and polo shirt. But the polo shirt had stains on it! I thought no one would notice but they are readily apparent in all the pictures. Where was my tie? Where was my jacket? It was her Masters graduation for goodness sake and there I am, a grown man, looking like a middle schooler. By the time she received her Doctorate some years later I thankfully had enough sense to put on a suit and tie in order to give the occasion, and the recipient, their proper respect.

So remember this the next time you meet up with friends, or take your kids somewhere, or go to dinner with your wife, or go over to your parents’ house for the holidays: Trust me…looking back, you’ll wish you dressed up.

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