Dad: “How much did I pay for those?”

I’m 14 and my dad is looking down at my khaki shorts that are fraying at the bottom and have a rip on one seam.

I smirk and say, “Forty bucks, but that was four years ago.”

My dad is an incredibly kind and generous man, so he didn’t actually care how much he spent on a pair
of shorts that my mom got me when we were doing back-to-school shopping. And I didn’t intentionally buy new shorts that were made to look distressed (read: destroyed), which I’m sure is what my father thought and which is why he was confused. He is an American dad after all, and American dads and fashion aren’t exactly the most cozy bedfellows.

The shorts were frayed and worn because I had worn them out through several years of adolescent use. What started out as a pricey pair of shorts turned into a pretty decent investment. I’m not that old, but $40 for a pair of shorts when I was 10 wasn’t cheap.

My dad is a finance guy – dialed when it comes to numbers. So I knew that when I told him they were forty bucks four years ago, he instantly quantified it as $10/year. A pretty minor clothing expense in the world of adolescent sons that tend to outgrow clothes long before they can wear them out.

Being a finance guy, my dad will shudder at me calling anything clothing related an investment, because most of us treat clothes as an expense, but the way I look at it – the longer an item of clothing serves you, the less clothes you will need to buy, which saves you money, and a penny saved is a penny earned, and earning based on a prior purchase decision is an investment right?

Let’s continue down this rabbit trail for another moment.

It is Spring, which for a lot of us, means Spring Cleaning. This is a time when we “find” all of the clothing items
that we have “lost” over the past year in the deep dark corners of our closets and dressers. Rediscovering these old pieces as we sift through everything in our wardrobe will push us to make decisions about what to keep and what to pass on.

We will keep our favorites. Those pieces that we feel like a total badass in, that fit just right, and that seem to get better with time.

These are your investment pieces.

We will donate the pieces that we have forgotten about. We forget about them because we don’t wear them, and we don’t wear them because they don’t fit right. They don’t make us feel like our best selves and they have only gotten worse with time.

Not investment pieces.

How do we end up returning to this familiar process every year? What merry-go-round did we jump on?

This process is familiar because our shopping decisions and habits don’t change. We buy items based on a gut feeling in a store or on an online sale – we keep it even though it’s just okay – and then we donate it a year later when it’s still just okay.

We think that we are saving money because it was cheap or on sale or both. And we do save money
if we only look at that one purchase. But what happens when we look at our wardrobe as a whole? Are fifteen “cheap” items that we never really wear that good of a deal? Or even worse, we absolutely love a piece of clothing but it becomes unwearable before we are finished wearing it because it was completely lacking in quality when we first bought it.

If you don’t mind chasing the fashion trends that change weekly and you don’t mind spending an incredible amount of time shopping, then you don’t need to buy for quality because there will be another shiny trend to chase before you can ever wear out the last trend.

But, if you want to take some stress out of your wardrobe (while giving your style a major boost), then you would benefit from choosing to invest in quality pieces that will outlive next year’s Spring Cleaning.

Those $40 khaki shorts weren’t the only investment piece from my youth – I had a $40 shirt too.

It was a pink, Polo Ralph Lauren button-down Oxford. It might have started out as an Easter shirt, but it quickly found its home in the staple section of my closet where it was put on heavy rotation and even played with my khaki shorts on a regular basis.

Unlike those khaki shorts, however, I actually never wore this shirt out. It was made with good materials, crafted in a quality manner, and cut in a timeless silhouette that never “fell out of fashion.”

It still isn’t “out of fashion.” I gave it to a friend when I outgrew it (my final growth-spurt made the decision for me) and he can still wear it with a pair of jeans and a sport coat in his day-to-day as a realtor.

How is that for an investment? It saved me money, it saved my friend money, and it isn’t finished yet.

That is the mark of a true investment piece – You have to decide when you are finished with it, because it won’t ever be finished with you.