When Is It Time To Let Something Go?

The warm temperatures of the new season have arrived. Even though I prefer the cold weather, I always get excited to start rotating my seasonal wardrobe.

Sweaters are swapped out for polo shirts. Corduroy for linen.

When items are packed away for a few months, it’s easy to forget the condition they were in at the end of the previous season’s use. Sometimes I’ll take something out of the closet and think, “Should I replace this?”

For the past three or four years I have asked myself that same question about my pair of navy boat shoes from Sperry.

I’ve had these shoes for probably close to ten years at this point. The leather insole is partially gone and the foam underneath it is disintegrating. Whenever I put them on my foot has to get used to the crumpled pieces of leather and foam, as if I had pebbles in my shoe.

Luckily, my brain can ignore the slight discomfort to the point where I don’t even feel it after a few minutes.

Why do I keep calling them for service year after year? Why don’t I simply get a new pair?

Well, I am too emotionally attached to these shoes to part with them. You see, these were the shoes I was wearing when both my sons were born.

It was a practical decision in the moment. Both my sons are warm-weather babies so I was wearing boat shoes daily up until the days my wife went into labor. I also wanted to make sure I was wearing shoes that were comfortable to walk and stand in and could be removed and put on easily. I thought a shoe with a non-slip sole was a good idea.

These shoes remind me of the very first time I saw both of my children. Every time I put them on, I think of those first magical days.

Because I was wearing those shoes when my kids were born, I was also wearing them the first time both boys met our dog and the first time my older son met his little brother.

Interestingly, while my wife was in labor, she asked me to just talk with her about anything that came to my mind since it helped her not focus on the discomfort.

I talked about my shoes.

At that time, before either kid was born, the emotional attachment I had to those shoes was because I had worn them on multiple vacations with her. I wore them in Paris the year prior. I wore them in Jamaica while on our honeymoon. My shoes already meant a lot to me from the adventures we had shared up to that point, but I wasn’t aware of how much stronger those feelings would become.

Another item of clothing I own that most people probably would have retired by now is a blue, Hyde Park, oxford-cloth, button-down shirt from Lands’ End.

I purchased this shirt over twelve years ago and it was one of the first items I bought when I got into menswear. Sure, I had dress shirts and ties and stuff before then but this was the first shirt I bought AFTER I had scoured sites like StyleForum and AskAndyAboutClothes. I was armed with a little bit of knowledge and that OCDB was the first item of “real” menswear in my crosshairs.

Over a decade later, the shirt is still soldiering on. The fabric on the collar and cuffs can’t really be described as “frayed”. “Non-existent” is more apt. The elbows are still intact, though, and I have never lost a button!

This shirt is so distressed that I would never wear it to the office. This shirt is strictly for casual instances. I’ll wear it with a chunky sweater or a thick tweed jacket. I’ll also wear it untucked with rolled sleeves in the summer.

Wherever I go, it’s always packed in my overnight bag.

That shirt is so important to me because it marks the beginning of something that would become a very large part of my life. Kind of like how restaurants frame the first dollar they make.

Another interesting aspect of that shirt is the way it smells. It sounds a little weird, but that shirt always smells like me, even right out of the wash. I don’t quite understand it. Maybe it’s because I’ve had it for so long, but none of my other clothes smell that way.

Its smell is comforting. When I put it on I feel happy and, in a way, safe.

Clothes and shoes are different from accessories like watches, necklaces, or rings. Those items are more durable and don’t experience the same wear and tear as clothes or shoes. Clothes and shoes have a much shorter lifespan so we are forced to decide what to do with them when they get old.

I think the two biggest factors to consider are your level of emotional attachment and the utility of the item. Like with my boat shoes and OCBD, if you are emotionally invested in an item and that item brings you joy, you’re more likely to put up with holes or stains. You’ll also be more likely repair an item if you have a connection with it. You might not darn the socks you got at the drug store, but you might patch the elbow of a shirt your wife bought you.

When it comes to utility, if the item is still serving all or part of its original purpose, then it probably still has time left to continue being part of your wardrobe. With my boat shoes, even though I am wearing them out, the outsole is still intact, which means I can still use them for, you know, shoes. With my OCBD, even though I can no longer wear the shirt in a business setting, I can still wear it casually. The item’s purpose has changed somewhat, but that’s ok.

But what happens when an item can no longer be used? What happens when I wear completely through my boat shoes? When happens when my OCBD is nothing but threads?

I don’t know. I guess I’ll cross that bridge when I come to it. I’ll probably keep them, just not wear them. I don’t think I could get rid of items that carry such personal, emotional significance.

I always say that your enjoyment of an item should increase with time. A lot of people get jazzed about the “newness” of something and then get bored of it when that newness inevitably wears off. The way I see it, the newness should play a very small part in your overall satisfaction with an item. An item should mean more to you as the years pass, since you’ll be making memories with it.

After years spent with a pair of shoes, or a shirt, or a watch, you should love that item more than the day you bought it, since the scuffs, dings, and scratches mean those items have accompanied you on your adventures.

I love my boat shoes because they remind me of my children. I love my OCBD because it reminds me of my long journey of personal growth.

People are always divided in their opinions of whether nor not it’s better to spend money on “stuff” or “experiences”. The people who like “stuff” are often seen as shallow and materialistic. I disagree with that. I feel the specialness of experiences is enhanced by the “stuff” since you can use the stuff to trigger memories of those experiences. Likewise, “stuff” is just a pile of junk until you have experiences using it.

I think my sadness over the prospect of letting go of the things I have emotional connections to stems from the fear of losing things that are special to me. I don’t want to lose any part of my kids’ childhoods and getting rid of my boat shoes feels like a little piece of that time will be gone. Getting rid of my OCBD feels like discarding a piece of myself.

Perhaps it’s a resistance to change. Perhaps having the same things year after year provides me with comfort in this very dynamic and unpredictable role of father.

Perhaps I get too attached to things. But the attachment is because of the people the things remind me of. Even though I put importance on material objects, I realize those objects would be nothing without the people I think about when I use them. That’s why gifts are so important to me.

I think the solution to all this is to keep making memories. Even if I were to get rid of my boat shoes or my OCBD, I would still be living my life with my beautiful children and amazing wife making new memories every single day.

Who knows what items I’ll be attached to ten years from now?