Use The Jeans Strategy To Save More For Retirement And Stay In Better Shape

The Jeans Strategy

Who doesn't like a pair of nice fitting jeans? Did you know that you can use the jeans strategy to save more for retirement and stay in better shape to boot? What the heck is the jeans strategy? Read on to learn how jeans can inspire you to save money and stay healthy.

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. Aha – the jeans strategy!

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.

And, 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!

Further Reading


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50 thoughts on “Use The Jeans Strategy To Save More For Retirement And Stay In Better Shape”

  1. I’m not spending $185 on a goddamned pair of jeans. But mother F’ER those James Jeans look good! A lot better than the complete KNOCK OFF $35 Lucky Jeans I recently bought at the COSTCO.

  2. Very creative! I’ve made the mistake of over washing my jeans so they fade and shrink. Now I only line dry and wash when they really need it. I also switched to stretchy jeans which last longer and are way more comfortable. I’ve never bought a pair of designer jeans. But I’ve basically followed your jeans rule just with more pairs that are cheaper. Fun post!

  3. Carlos @ TheFrugalWeds

    I appreciate the accountability of the jeans theory, which seems to parallel loss aversion. To avoid the pain of a perceived financial loss, you forced yourself to stay fit and kept them for a long time. 14 years later I would say you got your money’s worth.

  4. Ever since I lost all that (35-40 lbs.) about 35 years ago, I use the snugness of my jeans/trousers to remind me to be careful with my diet. I never intend to gain back that weight and so far so good. We all need reminders to keep us on track. This is true with weight, finances, etc. I think it is our desire to maintain a routine.

  5. Are jeans that last 14 years a guy thing? I’ve tried buying the expensive jeans based on the assumption that the quality must be higher to justify the cost. They weren’t. They stretched out of shape and wore out just as quickly as the $30 jeans I usually buy. No more expensive jeans for me.

  6. Oh Sam, I can relate! I had two babies- one in 2009 and another in 2011- and both times I was hellbent on getting back into my work clothes…quick. I had to dress up and even wear suits on certain days and there was no way that I was going to spend money on a whole new wardrobe when I already had perfectly good work clothes. Just another reason being cheap is awesome.

  7. I love the analogy and the site. At 48 and probably not planning to retire until I hit my official retirement age but I have been very aware recently that I have been running around in my financial fat pants and need to trim down and get things much more under control. The one positive side to this is I believe I am in a good financial position for retirement when it does happen.

    I just wish there had been a resource like this available when I first started out my career. I would probably be retired already ;)

  8. I like the logic, but this theory assumes you’re not going to somehow stain the jeans 6 months into owning them. Whether it’s red wine, grease, a permanent marker or an ink pen, I find myself replacing pants more often for stains than I do for wear and tear. Admittedly, it’s a bigger problem with khakis than jeans since they don’t show up as badly on jeans. I’ll stick to my Levis.

  9. David Michael

    Wow! Interesting theory around clothing and finances.

    As a person in my second adulthood (as Gail Sheehy would say) in my mid-seventies, I just bought a new pair of jeans in Costco for $15, size 32 waist. Really could have used a 33 inch waist but they didn’t have any so it looks like a few months of extra exercise and more veggies.

    I’ll be more than happy to buy another pair if these wear out and hopefully, with the same waist size. As for $200 for jeans…I’d rather put the money in P2P Loans and buy jeans in Costco with the accrued interest over time.

  10. mysticaltyger

    This is interesting because I did something very similar. When I hit my early 30s, I started gaining weight, but instead of going out and betting bigger pants, I ate less junk food and lost the weight. I simply don’t let my weight get over a certain point. If my pants are too tight, then I know I need to eat less and/or exercise more. It’s really not that difficult.

  11. You are not the first one to mention this one Sam..

    A mentor of mine mentioned the jeans strategy, you found it worked a treat for you?

    You used to be in Banking? Not too sure if you’ve mentioned this elsewhere but how long were you in that for?


    Jef (The Career Crusader)

  12. Great example on how getting good value out of something trumps paying the lowest price possible. It took me some time to realize that with shoes, you get what you pay for. A $20 pair of tennis shoes will wear out pretty quickly. But get a $100 pair, not only will it last longer but you will probably not wear it out as much because you want it to last longer after paying $100 for it.

    1. I do like getting criticized a little and being made to feel bad for spending $200 on jeans though. It’s always fascinating how people put their spending habits onto others. Personal finance at its finest!

      I want higher quality, longer lasting, better looking items in few quantities.

  13. I spent $300 for a tailored suite, soon after getting married some 15 years ago. I was worried I wouldn’t be able to wear it more than a few times. But now I’ve worn it about 12 times or more. Worth it after having gained 70 lbs (and then lost it prior to having to wear it again) … absolutely.
    $30 is about the maximum I’d ever consider spending on a pair of jeans.

    But I’ve bit the bullet on your “Make it hurt to make a difference”, by bumping my 401k up to 16%. This coming paycheck will hit me hard in the wallet! But in the long run will feel very good I’m sure.

  14. That’s a pretty commendable feat you’ve managed: staying in the same size jeans 10 years later after living in two of the best cities for restaurants. You must stay naturally skinny!

    I am somewhat of a designer so I have to have a little change and personality with my clothing.. I’m ok with shopping once a year to refresh my “palette”. It gives me energy, confidence, and I usually get compliments which is ice breakers for meeting new people and opening up more opportunities.

  15. Chris Minasian

    I think you mean you just bought a pair of “Joe’s Jean’s”…I don’t think there is such a thing called James Jeans?!?! That’s a good thing you got that incorrect! It shows how long you’ve been out of the jean market….great post!

  16. So guys use the same trick!? I have a favorite pair of jeans. If they don’t fit, my whole world turns upside down until they do. I’d rather starve than not fit the jeans!

    On a side note, the best place place to buy high-end designer jeans is a high-end consignment store. I bought my $200 jeans for $50. I couldn’t tell if they had ever been worn. I love that store.

    1. You are lucky to get a nice pair to fit from a consignment store! I used to do the same, but now that I’m only buying 1 pair every 10+ years, I figure I might as well go to The Blue Jeans bar, which specializes in selling boutique jeans.

  17. I am looking at this from a woman’s perspective, although I am not a shopper! This would not work for women during their child bearing years, just because we became pregnant. While you could argue that women need to work out to lose the weight and get back in shape, I would argue that the entire body changes after having a child. My hips, thighs, etc. all changed and even though I was the fittest I have been in years last year, my jeans prior to kids did not fit me, nor will they ever. I am ok with this.

    That being said, I do agree that buying certain clothing that is more expensive makes sense at times. I have nice shoes that go with certain outfits and I look and feel better in them.

    However, buying one pair of jeans in 14 years is awesome! If you want to spend $200 on them, go for it. You have saved plenty of money over the years by wearing only one pair.

    1. I love your perspective Kristy. Didn’t think about how one’s body changes post child birth, but now I have.

      Perhaps for a woman then….. maybe it’s not so much an expensive pair of jeans, but an expensive blouse or snug coat.

    2. I came searching down the comments for a woman’s perspective!
      For me, after our first child, I found my waist went back to its pre-pregnancy measurement, but my hips were wider than before and never went back! I still have all of my pre-pregnancy jeans 12 years later but haven’t worn them in all that time.

  18. couldn’t have been better timing on this article! So funny, cause I tried on a pair of my CH jeans this past Friday night and thought to myself…whoa, these are a tad snug! O.k. so its been a brutal winter here and I’ve comforted myself through it with many a tasty Belgian beer…but I thought the exact same thing Sam, no way am I not going to make these $200 jeans fit perfect again! Thankfully at 43 my waistline has only grown to 34″ from the 33″ in my college days…but I could totally see just “accepting” it and upsizing, hell the majority of my college friends long ago gave up that battle. Not me…at least not without a fight!

  19. Maybe I need to invest in an expensive pair of jeans, mine typically only last max a few years before they start wearing out regardless as to whether I got too big for them.

  20. insourcelife

    Interesting take… I guess I have a similar approach although I do have 3 pairs of jeans. The oldest pair is probably over 10 years old and all are 32″ waist which is what I wore back in college. The only difference is price – I can’t imagine spending $206 on one pair as each pair cost me about $30 on sale. They are Levi’s and Gap and look/work/last just fine. I guess what I’m saying is you don’t have to spend $200+ on jeans to use your approach. Plus you have an extra pair if the other one is dirty :)

    1. Everybody has a different spending tolerance, which is partially based on current income. This is why I didn’t put an absolute dollar amount in my Jeans Strategy, but said:

      “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. ”

      Based on my observation, I think once you start making over $150,000 – $200,000, you’ll feel less bad about spending $200 on a pair of jeans you’ll wear for a very long time. Which is why you should probably spend $500 on a pair if you want to stay in shape and use the Jeans Strategy!

  21. I just got a $26 pair of jeans… I should try James Jeans and see if they make me look hot. It might be too late at 40, though. I got a 30 waist and it fits well. It will give me the incentive to stay the same size over the next 10 years.
    You can still use the sizing as motivation without spending $206. :) I guess I’m just too cheap.

    1. I suppose everyone has their thing. I suppose it’s all relative. I used to scoff at going out to eat multiple times per day or splitting a check evenly when I knew my order was much less than others. In hindsight that was self-preservation, as I had just struck out on my own and wanted to make some serious progress in my savings/investments.

      Now, a few years later and making 50% more, I still get annoyed over the order splitting, but not because I think it’s unfair or because I mind picking up a check for a friend. Something about numbers not matching just bugs me in a visceral way. Must be some disease I picked up from being an accountant. :)

    2. With how studly you and Insourcelife life are, of course this article is irrelevant!

      But for those of us who struggle to stay in shape, I think this is a good trick.

      BTW, the trick to not feeling bad spending $200 on jeans is to simply make more money. Everything is relative.

  22. Funny! It must be PF fashion week – I just published an article this morning about attending to your wardrobe as well!

    I think the jeans strategy sounds like a great one for people who are conscious about spending. Unfortunately, for many, the cost of the jeans would fade away in their memories and not provide the same motivation in later months and years.

    I saw kudos to you for having the discipline for a strategy like this to work for you!

    1. You’re probably right about people forgetting. When I was in college, I could usually give a good estimate of how much I had spent the past day/week on food and entertainment. Mostly because at that time my budget was much smaller from mom and dad, and I was determined to spend their money wisely… much to the chagrin of my ex-gf who thought I was a money fanatic and that she wasn’t worth it. Probably good that we didn’t stay together as she hardly ever even tried to track her spending.

      Even now, a few years later and with many many times more expendable income, I still seem to track my “discretionary” spending on an ongoing basis (more out of habit than anything else). I’m not nearly as accurate as I was in college, but I do track to the nearest hundred still for overall spending, and can usually recall the amount (or will hunt down the credit card statement) for larger purchases… I paid ~$2,100 for my macbook 3.5 years ago and around $1,950 for my most recent update. (on a side note, I hope the upgraded HD screen and solid state drive will not be outdated for at least 4 years).

      I remember because I am determined to make it worthwhile!

    2. You’re probably right. But imagine if you spent $1,000 on a pair of jeans…… or were forced to do so. I would think most people would never let themselves go if they spent this amount!

      So, it all depends on how much one values money, fitness, and pain.

  23. The First Million is the Hardest

    I like this philosophy. I do something similar without even realizing it. I bought a nice suit a few years back when I was in about as good of shape as I’d ever been in. I use the few times per year that I have to throw a suit on as a barometer. If it starts to feel a little snug I know I need to start hitting the gym a little more, cause there’s no way I want to shell out that kind of money again just because I got lazy!

  24. Wall Street Playboys

    Sam this is one article where we are in 100% agreement. Do not agree with the buying homes argument (saving freedom) BUT this is spot on.

    Take it further.

    Even if you are still working you should also simply spring for two things:

    1) tailor made suits
    2) $250 shoes

    Why? Over the long-term it does significantly more help than harm.

    You don’t need to spend $2000 on a sit but simply having 2 nice suits form fitting, you have to stay in shape!

    Also for number two by having nice shoes you actually SAVE money in the long term.

    The quality of a show is enormous, you can simply buy show trees, shine them yourself and they will last 10 years.

    That is significantly longer than the 1-2 year time frame for a typical shoe.

    $50 per year with cheap shoes, $25 per year with nice shoes.

    Also as you stated
    1) you look better
    2) you feel better
    3) you increase your confidence

    Again you don’t need a billion nice items, just a few so you’re cognizant of your body and health.

    Great post!

    1. Speaking of suits… you are right! I have my Hugo Boss pin-stripe suit I bought for sale at Century 2000 back when it was next to the World Trade Center back in the fall of 1999! Totally forgot about that. I’ve patched holes in the bottom of the pants, but I might just give that suit a go again today.

      I agree with you on nice shoes too. Don’t need many, just a black and a brown one that have high quality leather and can be resoled.

      1. Nice post. I have a pair of slacks and a brown pair of shoes that I had custom made about 10 years ago durring a trip to Chile. The shoes were about $50 and the slacks were about $25. Lots of pesos, but reasonable for a gringo. I have worn each much more than anything else in my wardrobe. I noticed that the slacks were a little tight the last time I put them on, but maybe it is time to get a nice new pair in my nice new size, and hold myself to that new weight (I was rail thin before but am “normal” now).

  25. Good article. When I gain weight and my pants are getting uncomfortable I will use that as motivation to lose weight. If I keep gaining I will eventually buy a size up because the others are too tight. I hate doing this and it motivates me to really focus on getting back to my old size.

    When you only buy one pair over 10 years or so you can afford to spend $200 or so. Do they really look that much better though?

    1. It’s a different cut, actually the exact same one in the picture. They do look better b/c the color is a deep blue, and there are no frayed tassels at the bottom, so I can wear them with more formal clothing.

      14 year old (not 10 ear old) jeans definitely fade!

      B/c I was stubborn, I REFUSED to spend money on a size up.

  26. That’s an interesting philosophy. It’d work great if your intentions were honest and your resolve was sincere because all you’d need were those little reminders to stay the course. I can see lots of people just using that strategy as an excuse to buy overpriced items though. They’ll use that philosophy as justification for the purchase, but then they won’t stick to the “real reason.” Then they’ll just be left out-of-shape and with an expensive pair of jeans!

    The really important question is: Were you still receiving “You look hot in them” comments 14 years later?

    1. I think people are really rational beings. If you spend above your comfort zone for a particular item of clothing, then end up not being able to fit in them soon after, people would feel really, really stupid, as would I.

      I believe that folks who let themselves go have the highest self-esteem because they don’t care or care LESS of what other people think of them. I, on the other hand, did care in my 20s b/c I didn’t have money, was trying to climb the corporate ladder, and hadn’t found the one yet.

      Why else do you think people get all scruffy and chop off their hair after they get married?

      1. You have more faith than I do when it comes to people and rationality. It seems like the biggest flaw in some economic theory – the idea that people will behave in a rational manner. But emotions and feelings are completely irrational.

        On the other hand though I couldn’t agree with you more about travel being better than buying things. I actually wanted to write something soon about how there have been studies cited by the Economist that show people’s experiences (travel, being with friends, etc) produce lasting happiness in comparison to materialism. In the end thats what we all want, so why not make sure we’re using our money to maximize our happiness.

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