Who doesn’t like a pair of nice fitting jeans? For the first time in 14 years I bought myself a new pair. My old boot cut jeans were purchased back at the Diesel flagship store in Manhattan a month after I got my first bonus in 1999. I’m surprised they’ve lasted this long. There’s nothing wrong with them, it’s just that the bottoms have started to fray and the color has faded.
I’m a pretty minimalistic guy when it comes to clothing. I enjoy wearing the same outfits over and over again probably because I’m lazy when it comes to fashion. Jeans and a t-shirt or jeans with a long sleeve collared shirt and a blazer are the cleanest looks in my opinion. I also enjoy using things until the max. My 2000 Land Rover is a perfect example of “if it works, no need to change” attitude. Shopping for clothes on a constant basis brings little joy. I’d much rather spend my money traveling.
THE JEANS STRATEGY
Theory: If all you could ever buy was clothing that fit you at the peak of your physique, would you be more attentive to watching what you eat and stay in better shape? This was the question I asked myself to help control my growing waistline back when I first started working.
The pair of Diesel jeans I bought in 2000 cost $160. I clearly remember thinking to myself, “holy crap this is a lot of money for a pair of jeans I probably can only wear on weekends.” I also remember thinking how tight they were with a 33″ waist. I was already starting to gain weight working all those banker hours and the 32″ inch waist jeans I owned in college was slowly becoming a distant memory.
As I hesitated to fork over the largest amount of money ever for an item of clothing, the sales woman deftly said, “You look hot in them.” Of course my money and I soon departed.
Once I paid for the jeans I vowed to never buy another pair until they broke. I felt an enormous amount of buyers remorse. I also promised not to gain too much more weight because I would feel absolutely stupid if I couldn’t fit in the jeans several months later.
The guilt of spending so much more money on a pair of Diesel jeans vs. a classic $48 pair of Levi’s jeans made me control my clothes spending habits for over a decade. I would still shop for clothes during sales every couple of years, but I would never spend an exorbitant amount of money. I’d buy GAP polo shirts 40% off for $15 or a pair of Banana Republic khakis on sale for $30 and that’s it. Also, I didn’t buy another pair of jeans to keep my promise.
Because the Diesel jeans were snug and a little uncomfortable when I sat down, I was constantly reminded to always eat in moderation. If I let myself go, the pair of jeans would simply be too uncomfortable to wear. This mentality really stuck with me over the years as my income continued to grow. I truly believe these pair of jeans acted as a terrific anchor mechanism for saving me money and keeping fit.
I didn’t want to cheat by buying clothes that fit a yo-yo sized body. I wanted to always fit in clothes that I bought as a 22-year-old as long as they lasted. I knew if I did, at least I’d always look reasonably fit for the rest of my life. Jeans are the longest lasting items of clothing, hence the Jeans strategy. If a t-shirt was even longer lasting, then I’d write about The T-Shirt Strategy to save more and stay in better shape.
The jeans strategy for saving money and staying fit: Buy one pair of well-fitted jeans that costs at least 2X what you’d normally pay during peak physical fitness and vow to never buy another pair again until they break.
MAKE IT HURT TO MAKE A DIFFERENCE
If you don’t make the initial expenditure hurt (money and physical discomfort), it’s hard to change your habits. Getting in trouble the summer after high school hurt enough for me to focus during college. Losing a girlfriend to another guy hurt enough to not take girlfriends for granted. Having my net worth almost get cut in half during the financial crisis in 2008-2009 hurt enough for me to start this site and learn how to actively diversify my income streams.
If you feel good about the way you look, I’m absolutely positive you’ll do better work than if you’re always feeling self-conscious about your weight. You’ll naturally become more optimistic about everything and people will probably treat you a little better as well. Socializing with new people becomes easier because you’re more confident. You might even save a lot of money and time along the way because you’re happy with exactly what you have.
So what did I end up buying? I ended up paying $206 after tax and hemming for a pair of James Jeans. I’ve never heard of the brand, but apparently they are a coveted boutique brand that produces a limited batch of jeans out of Southern California. Yes, I know $206 is a lot to spend, but I talked them down from ~$265.
Although the saleswoman said I should go with a 32″ waist for a tighter fit, I decided to play it safe with a 33″ waist and give myself a half inch of cushion instead. I’m no longer hurting for cash like I was as a 22-year-old. But I do plan to make these jeans fit for another 10 years until I’m 46!
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Updated for 2020 and beyond.