The Case for Investing in Quality Clothing, Part 1
How buying a pair of $450 boots a decade ago shaped the way I buy clothing today.
In 2014 I was 19 working my first salaried adult job while living at home with mom & dad and not paying any bills. It was a glorious time in my life where everything I wanted, I purchased. It was a purely feral desire to spend money on anything I set my eyes upon without considering the cost. I was thriving.
This was right around the time Kanye started wearing the tan suede Common Project chelsea boots and I felt compelled to mimic what I saw on message boards and forums online (just want to clarify 2014 Mariano and 2024 Mariano have very different thoughts on Kanye West). I remember the smell of the box. I remember the handwritten note from End. I remember the excitement of knowing I had spent so much money on a pair of boots. I wore those things every single day for a month until the heel tabs randomly come undone and tore off. It’s understandable that products will fail, but at 19 and having spent $400 on them I was extremely disappointed. After a quick email to End, they offered to exchange the boots for a new pair orrrrr…they offered to give me credit to purchase something else from the site. I refused to get another pair of Common Projects and so I scoured their site and ended up ultimately deciding on a pair of Stephen Chelsea boots from a brand I had never heard of called Trickers.

They were $450 in 2014. They’re almost double that in 2024. And still wear them at least once a week.
Was $450 a lot of money in 2014? YEAHHHHHH. But I was hopeful that I’d wear them over and over and over into the future. In some seasons, that meant every day for weeks at a time. In others I actually forgot I even owned them and would be surprised to find them buried in my closet. Now I’m looking at getting them resoled with a Vibram commando sole with Goods & Services in LA.
Here’s my sales pitch: It was a wise financial decision to spend $450 a decade ago for boots I still wear today. That’s a $45/year investment.
I overheard someone recently said they buy a new pair of boots from Zara or Aldos every winter and beat them into the ground by the time spring comes. In the last decade, that’s at least $100 a year for 10 years, or +$1,000 for some poorly constructed and surely uncomfortable boots. Not only is that a waste of money for shoes that you can’t wear past a year, but it’s also an extremely wasteful way to look at clothing and shopping.


Here are some things to consider before spending $450 on a pair of boots (or any amount of $$$ on clothing):
More money does not (always) mean more good. The temptation to believe that a $$$ product is going to be more durable or comfortable or better than a $ product is real, but that isn’t necessarily true. A lot of $$$ products are that expensive because of name and name alone. You can spend a lot of money on garbage, and you can also spend very little money on something great and timeless. There’s a reason why the Dickies 874 work pants are so popular — they’re durable and also still $30! When it comes to spending money you have to…
Research, research, research. Once you break away from the idea that spending $$$ is always going to get you the best product you buy, it’s time to start looking at what’s out there. Personally I have an unwritten rule that I’ll spend a few weeks (or months) ((or in the case of the Drakes raglan, 3 years)) researching a product to see if it’s worth buying. In some cases, you’ll stumble upon a reddit thread that will let you know that the jacket you were looking into is actually garbage. Save yourself the buyers remorse and just Google “_________ product review,“ you’ll find articles and blog posts and YouTube videos that might guide your opinions.
Some brands are worth the money. I’ll be honest, I really lucked out with the Trickers. I had no idea whether or not they’d last, I just thought they looked good. After all these years of wear, and having purchased other shoes that haven’t lasted nearly as long, it’s become clear to me that not all brands are created equal. Not every boot has the ability to last a decade. Not every boot can be resoled. Not every boot has leather that can withstand northeastern winters. And to get that level of quality, it came at the price tag of $450. In hindsight, that’s money well spent.
If the price is too high, either save up or consider shopping second-hand. There’s no shame in putting some money away for a future purchase, especially if it’s something that you plan on keeping for a long time. My wife actually had a savings fund set up for me for my Drakes coat and that helped soften the blow when it was time to make the purchase. You don’t always need to have the thing you want right now; be patient, wait it out, and look for sales. Alternatively, I proudly lowball people on Grailed. I’ve managed to get absolute STEALS on that site. I’m talking about scoring brand new Visvim boots with stickers still on for $1,200 off types of deals. If you’re patient, can negotiate, and are kind to the sellers, you’ll be surprised with what you’ll be able to find. I haven’t used Depop or Poshmark myself but I’ve been told you can find deals there too.
Finally…resist the urge to give into the capitalistic idea that owning more things is a good thing that will somehow fulfill that gaping hole in your soul. Recently my wife and I have been selling / giving away / donating clothing that we no longer wear and it has been wonderful. Apart from gaining closet space back, it also has allowed us to really wear the things that we like more often and enjoy them for what they are. I think owning ONE pair of boots you really love and that you saved up for is so much better for you (and the environment) than owning 4-5 pairs of cheap boots that you sort of like. In a world that says BUY BUY BUY, sometimes the most punk thing to do is to buy well, buy less, and wear it into the ground.
Sometimes the quality is worth it, even if it comes at a price. Once you decide that something has PHYSICAL DURABILITY, you now need to decide if it has EMOTIONAL DURABILITY. Sub to the newsletter below and stay tuned as we dive into that next week in Part 2 — Just because something can last for a decade, will you want to wear it for a decade? See you next week boys (and the 3 girls that read this).