Contrarian Shopping: 20 Things I’m Willing to Pay More For

There’s a lot to be said for contrarian investing. Famous investors like Warren Buffett and Jim Rogers are routinely lauded for going against the herd and purchasing unwanted stocks at bargain bin prices.

Interestingly enough, nobody ever gets credit for contrarian shopping — that is, purposely choosing to pay more for certain products and services.

Don’t believe me?

A recent Google search on the term “contrarian investing” turned up almost a half-million results.

As for “shopping contrarians”: 23,500.

I know what you’re thinking: Len, why would I ever pay more for something if I didn’t have to?

It turns out there are plenty of reasons, including:

  • Added convenience
  • Better quality
  • Environmental friendliness
  • Superior customer service
  • Additional security via guarantees

With that in mind, I thought I’d put together this quick summary of things I’m willing to pay more for. What’s on your list?

Bed sheets. I figure since I spend roughly one-third of my life in bed, I may as well be as comfortable as possible. The key is knowing that higher thread counts eventually reach a point of diminishing returns.

Nonstop flights. For me, the ability to bypass a layover — or maybe even two — and avoid flight delays is usually well-worth the price premium.

Extra leg room. When flying economy class domestically, I’ll often pay an extra $40 to $100 for so-called “premium coach” seats with more leg room. Those extra inches make all the difference in the world — especially on longer flights.

Food. Eating is one of life’s simple pleasures — which is why I always buy high-quality food. That being said, I never overpay for organic produce.

Internet service. There’s nothing worse than a slow Internet connection, so I have no qualms paying an extra $20 per month for service that’s up to 15 times faster.

Soap. Awhile back the Honeybee started buying low-priced tinted “designer” liquid soaps. Unfortunately, they don’t cut through grease. At all. But, hey, at least the soaps are now color-coordinated with our remodeled kitchen and bathrooms!

Appliances. Although they typically have higher upfront costs, the payback period of gas appliances tends to be relatively quick because natural gas is cheaper than electricity in most places.

Carpet pad. I always pay extra for a thicker carpet pad. It not only provides added comfort, but it also extends carpet life too.

Coffee. I’m talking about the stuff I brew at home. I can’t stand Folgers coffee — besides, Folgers is more expensive than you might think. We pay extra for the Dunkin Donuts brand — or sometimes a premium whole-bean coffee that we have to grind ourselves.

Tools. It’s simple; I pay more for Sears’ Craftsman tools because of their ironclad guarantee: If for any reason your Craftsman hand tool ever fails to provide complete satisfaction, return it to any Sears store or other Craftsman outlet in the United States for free repair or replacement. (No, I don’t work for Sears.)

Home maintenance. My home is my castle and so I treat it as such; I refuse to hire unlicensed contractors or use shoddy materials on my most important purchase.

Comfort. Speaking of my castle, I’m not the type who is willing to bundle up at home just to save a few bucks on the heating bill. And during summer, we’ll run the A/C at a reasonable setting to stay cool and comfortable too.

A nice neighborhood. I’ll always pay more — or trade 200 square feet of living space — for the opportunity to live in a better neighborhood.

Toilet paper. Trust me: Cheaper toilet paper actually costs more in the long run because it requires much more product to, um, get the job done. I’m sure Sheryl Crow, who advocates using only one sheet per visit, will back me up on this.

Shoes. If you spend a lot of time on your feet, a good comfortable pair of shoes is an absolute necessity for avoiding blisters, sore feet and other problems.

Lodging.Trust me; trying to cram four people into a cut-rate no-frills hotel room is the quickest way to ruin a family vacation. We don’t skimp when traveling now; we only stay in hotels that offer multi-room suites.

Beer. Because life really is too short to drink cheap beer, folks.

Desk chair. I hate to admit this, but there are days when I sit at my desk for 10 or 12 hours with few breaks in between. I couldn’t do that with a substandard chair.

Open highway. I save about 20 minutes on my daily commute home because I pay $5 to use the express lane. That’s a bargain considering I’m only paying around $1250 annually to free up 83 additional hours of my valuable time.

Clothes. While most kids tend to outgrow their clothes before they wear out, it’s a different story for adults. Over the long run, good quality clothes are often the better deal. Heck, I have coats and jackets that are a decade or more old — and yes, they’re still in style. Well … at least I think they are.

Photo Credit: Thomas Quine


  1. 1


    I have some custom made tailored slacks and coats that were made almost 20 years ago by a competent Indian tailor from Hong Kong. Remarkable that the classic style is in fashion, even more remarkable that the slacks still fit my waistline (with only a little effort).

    • 2

      Len Penzo says

      And if even if the stuff goes out of style, if you wait long enough it eventually comes back in style!

  2. 3


    Sheets and shoes are at the top of my quality vs quantity list too. I still kick myself for buying flannel sheets that were just a little bit cheaper than my normal brand but pilled after one washing. That is one expensive drop cloth that I now have. I would also put mattress on that list too.

    Non-stop flights have been added to the list once we had children and time off became harder to come by…although I had no problems with longer flights when I was younger, poorer and single.

    Great list.

  3. 5

    Cindy says

    I think you covered some good ones. I’m with you on cheap coffee. I’d include disposable diapers on that list too!

  4. 7


    I’m definitely more willing to pay more on this kind of stuff too. If you try to save money on every single expense you’ll just be unhappy and it will sometimes cost you more in the long run. The one that I would go against is cheap beer. I’m not particularly picky about my beer and enjoy some of the cheap brands just as much. Then again, if you really enjoy the better beer, that extra money would be worthwhile. I also tend to be cheap on my clothes, but I don’t sacrifice quality for my cheapness.

    • 8

      Len Penzo says

      With respect to beer, I felt the same way when I was younger. I remember in college buying the cheaper stuff to stretch my money because, for me, it was simply more a matter of quantity over quality at the time.

      Nowadays it only takes me two beers in the evening to guarantee a hangover the next morning. LOL

  5. 9


    Over the years, I generally defer to quality in everthing i buy. I would rather have a smaller quantitiy, but higher quality. Most people waste their spending on cheap stuff and lots of it.

    • 10

      Len Penzo says

      Same for me. Age (and increasing income) has influenced my increased attention to better quality and more convenience.

    • 12

      Len Penzo says

      I can think of more than a few things though where you can buy high-quality stuff where it makes little sense too — but that is the topic for another post.

  6. 13

    Oscar says

    These 20 things represent a pretty significant chunk of your life and your expenses – why not just come out and say that, on the whole, you’d rather pay for quality and convenience than not? Nobody’s going to judge you – heck I myself am noticing that “frugal” is often a disguise for “cheap POS”.

    • 14

      Len Penzo says

      Because this is a blog post about things I’m willing to pay more for. If I took your advice, instead of a blog post I’d be left with a 140-character statement better-suited for Twitter — and nowhere near as informative. 😉

  7. 15


    I’d add “pillow” and “mattress” to the list for the same reason as bedsheets. I’m a lifelong devotee to the expensive Tempur-Pedic brand, and no folks, I’m not getting paid to promote them.

    And I buy nice whole-bean coffee that I grind in the mornings, then put into a French press. But, of course, I save a few bucks by getting it from CostCo. That counts, right?

  8. 18

    Lola says

    Life is too short to eat cheap (bad) food, drink cheap wine (or beer), or sleep in a cheap bed! I also pay more for the Dunkin brand of coffee ~ Folgers sux. :)

    • 20

      Tony says

      Just a quick note about Folgers coffee. Most Folgers isn’t very good but if you can find Folgers “Pure Columbian”…. Nectar of the Gods!

      • 21

        Special Ed says

        I started roasting my own coffee a few years ago. I buy raw beans in bulk and control the entire process from the roast to grinding to brewing. I drink, literally, the best coffee I’ve ever had, every day. There is a learning curve, but it is so worth it. And it is actually very frugal. Once I got the process down, I spend maybe an hour a week roasting and the brewing process is simple.

        Two other things I don’t skimp on are cigars and a good single malt whisky.

  9. 23


    What are your thoughts on business class for a long flight? Our company policy allows it and that’s what I fly when going overseas, but I don’t think I’d spend $5K of my own money to do it on vacation. It’s easier to spend the company’s money than your own – is that wrong?

    • 24

      Len Penzo says

      My company’s policy is everyone is entitled to business class for overseas travel too. If it is policy, then there is no need to feel guilty taking it, IMO!

      If I was flying to Australia — or taking a flight 8 hours or longer — for pleasure, I’d at least consider business class. I don’t think I’d know what I’d really do though until I was actually in such a position. I was reading in the Wall St. Journal that many airlines have something like a “premium economy class” for overseas flights that falls between business and coach; that may be good enough.

  10. 25

    Jill says

    For an extra charge, Six Flags Magic Mountain offers passes that let you jump to the front of every line. Well worth it!

  11. 27


    Its interesting that healthcare wasn’t on your list of things you wouldn’t be willing to pay more for. Good healtcare is worth paying more for especially if you find a skilled clinician who’s office provides exceptional service. Its sad that today medical/ dentalcare is often viewed as a commodity. Look around…..there is a huge variation in the quality of care that exists.

    • 28

      Len Penzo says

      You know, it didn’t cross my mind, Dr. Frank. You make a great observation! I have no qualms paying more for better healthcare either — so there’s 21 things I am willing to pay more for!

    • 29

      Betsy22 says

      I was thinking this too. I happily pay quite a bit for my dental care (not covered under my insurance), since I think that I could spend the rest of my life regretting bad dental decisions (have seen this happen to friends and family). On the other hand, I go pretty cut-rate for my annual vision exam – I think that most docs are going to get it pretty much right. However, I’ve never understood the LASIK advertisemts focusing on price – if someone’s zapping my eyes, saving a thousand dollars is not the biggest concern for me.

  12. 30

    K Williams says


    Agree on the neighborhood part…I paid extra for my back yard that has a green belt behind it, whereas the rest of the neighborhood does not have this luxury…well worth it!

    Kenny E. Williams

  13. 32

    debbie z says

    I would add kitchen knives to the list. I want a knife that stays sharp, it is easier and safer to use.

    I buy about 60% of what I buy nowadays at estate sales, you can often find furniture, linens, kitchen items, new clothing/shoes, hand and power tools, sports equipment etc that are better quality than you could afford otherwise very cheaply – like about 10-20% of the cost elsewhere. I certainly pay far less than I would even at off price retailers, and there is no packaging!

    I have bought nice antique furniture, Craftsman tools and top quality linens all at one sale and walked out with a solid oak 6 foot x 34 inch bookcase, 3 sets of 600 tc sheets and a whole set of Craftsmen pliers, screwdrivers and 2 electric tools still in original boxes w/all paperwork for less than $100. I estimate that I paid less than 20% of the current second hand value for top quality and that’s worth the time and gas to go and get it.

  14. 33

    Beckybeq says

    School district, while I have kids. When we moved, we interviewed different districts and decided on the one we wanted our kids to go to. (Important decision – one child with autism, one child in the gifted program.) We figured the premium on the house we bought was about 20% – and worth every penny.

  15. 34


    I buy expensive clothes for very little money…except for bras.

    I pay more for bras than any other item in my closet. In fact, more than for all my other clothes COMBINED.

    There are no cheap bras in my size.

  16. 35

    Kathy says

    I’m with you on almost everything you listed, other than perhaps, coffee. I honestly can’t tell one brand from another. Along with sheets, I spend more on really good towels. We are building a new house and we are not skimping on materials like 2×6 outside wall studs to allow for extra insulation, high quality windows with better insulating value, extra drainage tiling for moisture control, and a water softener and filter for our water system. Ultimately, we are hoping that these extra costs now will save us money for future utility bills plus less needed maintenance on the house.

  17. 36


    That’s a great list and you’ve basically covered everything. I wish I could say the same thing but I’m in a saving mode and so I try to go cheap in any way I can.

  18. 37


    I think “cheap” beer and “low quality” beer may not be the same thing.

    A friend worked at Miller and said that they would make Milwaukee’s Best out of whatever more premium beer they had left over at the end of the day. The Beast gets such a bad name because of where it’s marketed, not how its made.

    That’s not to say any American-style lager would qualify as good beer :-), but I’ve found that if I Pepsi-challenge various beers I often find the cheap one is just as good – or better.

    Perhaps another Len Penzo blind taste test???

  19. 39


    I completely agree with you about the beer, life is too short not to enjoy the good stuff! As for tools, I’m more of a Snap-On tool guy myself, but have the same philosophy on paying a premium price for the guarantee.

  20. 40


    Amen to the coffee. My wife and I prefer Italian brands like Illy or Lavazza for our home brew, perked on the stove top in a stainless steel Bialetti pot. And we will buy the local store brand whole bean, and grind it ourselves. Makes a fantastic cup o’ Joe.

  21. 41

    Ellis says

    I’m willing to pay more to get good-quality paint. Whether you’re painting your house, your porch, or a room inside, the most valuable thing is your time. I’d rather buy a good-quality paint and do a job that takes fewer coats of paint. Your paint job will probably last longer, too, before it needs to be done again.


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