Putting My Faith in Boots That Pinch

Me in my brown Frye boots, circa 1985.

I have this freakin’ awesome pair of brown leather Frye boots.

I got them in 1985, before I went to college.

They cost $172.00.

I remember holding my breath as the cashier took all my bills and slipped them into the register.

When she handed me the bag, I thought I might throw-up.

That first semester I walked around campus with bloody heels, praying my investment would eventually pay off.

I’d dreamed of soft chocolate boots, like the couches the people I’d babysat for owned.

But my new boots were stiff and unyielding.

Those suckers took forever to break in. 

Somewhere along the way, they stopped hurting.

And when I wear them now, someone always admires my kicks and asks me where I got them.

I like to watch their faces when I say I got them in a shoe store that closed in 1989.

Ten years ago, I promised myself that if I ever found a similar pair in black, I would buy them – price-be-damned.

Recently, I was not shopping for shoes when I saw the sister pair to my old brown Fryes: tall black boots with a buckle.

I looked at the bottom of the sole to find the price tag and sucked in my breath.

It’s always been hard for me to spend money on myself. 

“You’ll have those forever,” said the well-dressed saleswomen who handed me an oversized white box.

I slipped the boots over my stockings and took a few steps.

Omigosh. They. Hurt. So. Much.

I found a chair and tugged them off.

“What do you think?” the saleswoman asked.

What did I think?

I thought only a crazy person would buy boots at that price that were that uncomfortable.

And yet.

I remembered.

My old boots had been awful, too.

It had taken years to get them to a place where I could call them comfortable.

But they have been my signature footwear for decades.

So I held my breath as the cashier scanned my credit card.

Because they cost a lot more than they did in 1985.

And I brought them home.

And while my new boots look freakin’ awesome, I’m back to bloody heels and Band-Aids.

Right now, I’m faking it.

Pretending every step doesn’t hurt.

I have to believe that eventually these boots will be right.

Because sometimes having something worthwhile means enduring a little pain.

Ask a newly published author. Or any woman who has given birth.

Have you ever made an expensive purchase that you fretted over? What was it? How’d it turn out? 

tweet this twit @rasjacobson

This week the directions were to write a piece using the idea of money as inspiration — in under 450 words. I did it in 419. 

101 responses to “Putting My Faith in Boots That Pinch

  1. Frye boots are back in style. My daughter just bought a pair.
    Buyers remorse? Oh yeah. It happens…Sometimes things just look or feel good in the store when I’m surrounded by beautiful things.


  2. I can’t believe you actually bought boots that hurt. I’ve never been able to break boots in if they hurt that much in the first place. Obviously I don’t have your sticking power because it seems to work eventually…. for you


  3. I haven’t done something like that in a long time. But I remember being young enough and dumb enough to do things like that! I’d like to say that it always worked out but I’d be lying. It really did work out sometimes at least.


    • Ack! I hope that if I just keep wearing them a little bit each day eventually my feet will either toughen up. (Oh, that sounds appealing.) Or those dang boots will give in to me.

      It is definitely a battle of the wills right now.

      I will win.


  4. I know, I understand. I have always wanted to hire someone to break in my new shoes


  5. Yay, you got them!


  6. I want your boots. I tried on several pairs of fall-ish boots last week and each one hurt like hell. I didn’t buy any. But I want to look cute so I’ll have to go back and suck it up and buy a pair. I also have a very hard time spending any money on myself. Must be a mom thing.


    • Dar: It is sooooooo hard for me to spend money on myself. For Tech, I’ll get him anything: no problem. Dude needs a winter coat? No problem. Dude needs new gloves. Of course, he does. Hands grow, too. Done.

      Meanwhile, I’ve had a size 7 foot for 30 years, and prior to this purchase, I had 8 pairs of shoes — including sneakers & flip-flops. Why can’t I feel comfortable investing in me?

      Apparently because I make stooopid purchases like this.

      These boots should be great when I’m 80. Seriously, I’ll be the hottest old lady in the nursing home. 😉


  7. Oh dear! I just went to their website and fell in love with no fewer than four pairs of boots. I can afford zero pairs. Now I have inner turmoil.


  8. I bought an obscenely expensive denim jacket for my first child when he was just a few months old. An infant jacket that I paid as much for as I would one for myself that I would wear for years. (Remeber, I live in a sub-tropical climate. Jackets are frivolous here.) But it was so stinkin’ cute! I dressed him in it and took some photos. He wore it a dozen or so times, and I put it away in a crate of outgrown things.

    Then the little brother was born, and I pulled it out. It was even softer than I remembered, and looked so stinkin’ cute on little brother! I took some photos and put it away.

    Then — well, you know what happened. Another brother, another season with that jacket. More photos. More stinkin’ cuteness! The jacket is now in a crate of things I’m keeping for posterity. With a little luck, I’ll get to pull it out again someday for some grandkid cuteness!


    • Omigosh Lisha! I love that story. That jacket was an investment! At this point it is a family heirloom!

      And if I understand your super secret subtext, I think what you were trying to say is that if I hold onto these boots long enough, one day TechSupport’s daughter might want to wear them. That would be so special. That is what you were getting at, wasn’t it?

      All sarcasm aside, you should TOTALLY use your comment here as part of a blog post. It has the makings of something special: a frivolous purchase turned family heirloom. Think about it. I’m tearing up just thinking about it. If you have photos, you could post them. I’d LOVE to see each boy in that jacket. Just sayin’!


    • I had outfits like this for my wee cherub boys when they were, well…wee cherubs. Two years ago, I had a good friend take a box full of my favourites and quilt them into a snuggly blanket for my mum.

      This year, I hope to have the same thing done for me – a king-sized memory of the first 4 best years of each child.


    • Lisha: You and Liz would really hit it off! On a million levels! Please read each there’s blogs! 😉


  9. I am not a shoe girl. I just don’t get that thrill of buying that adorable pair of shoes to match the one outfit I have. Mostly because those adorable shoes usually hurt like hell, and I like to be comfy walking around. I own a woefully small amount of footwear for a girl. It is shamefull.

    When I went to Italy many years ago, it was around the time the boot trend was coming back (late 90’s, but really, does it ever go out of style?), and I must have tried on a bajillion pairs because I wanted to look cute like all those adorable Italian girls. But I have huge calves and boots are not my friend. I was so very sad. 😦

    I am happy for you and your new boots. I hope you make each other very happy for years to come. And I hope you break them in soon. Nothing worse than sore feetsies. Good for you for splurging on yourself. It is rare for a mom to do, and you deserve it! 🙂


    • Misty: I have HUGE calves. And I am soooo not a shopper. That’s why Fryes work for me. They are slip-ons — not zippers! They go over my double-wide meaty calves.

      That’s why it was near impossible to say no.

      I have an Italian shoe story, too! I bought a pair of green suede sling-backs because everyone was all: “You’re in Florence. You have to get shoes and a handbag.” So I bought the shoes. The heel broke off the moment we arrived in Venice. I wasn’t even wearing them. The hell just came off in my suitcase. I don’t know how many lira they cost me, but I was a student at the time. Why did I even think I needed green suede sling-backs?

      Since then I have stuck to the basics. Black heels, sneakers, flip-flops, my brown boots — which I already owned! 😉


  10. This week’s Writing Challenge has something to do with simile and metaphor. I think your boots fit.


    • I wanted to be more explicit — but the word count kept me limited. I wanted to get to the message more. About pain and how it CAN be worth it. You are the only person to have picked up on this.

      Have to check out the writing challenge. Maybe I can retool this. 😉


      • I had a comment-discussion the other day with a poet blogger about our mutual appreciation for the way William Stafford’s poems subtly sink in long after you read them. I’m one of those who appreciates subtlety and nuance and ultimately finds it more powerful.

        P.S. Those are awesome kicks. I also appreciate nice boots. 🙂


  11. Funnily enough, those jeans of mine you’re so fond of fall into that category. I’ve always worn 501’s. Always. My wife hates them because she says they’re just not flattering. She’s pushed me toward nicer jeans but I always think they looked so “Ooh, look at me in my spangly, silky denim!” on me.

    Then I discovered the Diesel store. Where jeans are easily 5 times as expensive as 501’s. But they look like jeans. I think I mostly bought them because my wife said there was NO WAY I was going to buy them, so I had to… you know… marriage. Immediately loved them. A month later bought another pair I love even more so I’d have something else to wear. Haven’t regretted it yet.


  12. Absolute home run!! (And not just because I was leaving for college in 1989, too.) Such a great flow of concepts, and I loved the way everything tied in to the idea that some things are expensive in terms that go beyond money, but end up being worth it!


    • Thank you for picking up on that. The word count prevented me from elaborating, but that is where I was heading. Like, isn’t childbirth worth it? And that hurts. What about getting a tattoo? That hurts. But people love their tats. Ear piercings? Or writing a great piece of literature? Ouch!

      That commitment, that is what keeps me wearing those boots a little bit, every day.

      Nice to meet you! 😉


  13. I have, many times. I don’t have a lot of stuff, but the stuff I do have lasts a while.

    I also like your analogy! It’s true that worthwhile relationships, accomplishments, and….things don’t come without an effort.


    • Right? As writers, we know you have to struggle the right words. And it isn’t always easy. Oh thank you for picking up on my analogy. The word count prevented me from being more explicit.

      And thank you for not making me feel like a total dooj.


  14. Sorry that I’m still pinching you, but I promise to stop.


  15. I can’t buy boots or shoes anymore than need breaking in, as I have hammer toes made worse by an injury and it just hurts too much. (I was going to give you a link to what hammer toes look like but it hurts just looking at them!) So – rather you than me! 😉

    As for whether I’ve ever bought anything expensive that I’ve fretted over – almost certainly but my fretting mind won’t let me remember what it was!


  16. I saw a segment on The Today Show with household tips. They suggested for shoes that are a little too snug, put on a few pairs of thick socks (maybe rag wool, depending on how much you want to stretch them) then put the shoes on. Then take a hair dryer and blow around the areas you need to stretch, or the whole shoe, whatevs. Get the leather/pleather heated up. This will allow the leather to stretch. Then keep them on your feet until they cool down and mold to the new stretched out size. Ta da!

    I haven’t tried it yet ‘cuz I don’t think I have any too tight at the moment, but it sounds logical! (my problem is shoes fit normal up front but I have a really narrow heel and they fall off the back, let me know if you find a solution for that lol)


  17. If you break them in and they stretch to a size 10, you could send them to Canada. 🙂


  18. Omigosh, Renee! In the summer of 1986, I saved and saved my $$ and bought a Gucci purse. My mom was so mad that I spent that much ($100!) on a purse, but I just told her I had been eyeing it all year long and it would last me forever. Yes, I still use that bag. And I regret the fact that I can’t even buy a Gucci wallet for ONLY $100 these days….
    Sometimes you DO get what you pay for 🙂


  19. You probably had the boots pumped too much.


  20. It is so hard to spend money on ourselves… why is that? My husband actually encouraged me to buy a nice bag for work, and I went right back to the old and faithful cheap-but-good-enough. I am glad for BOTH your pairs of boots and wish you well with the blisters!!



  21. I covet a particular pair of Frye boots but haven’t been able to let myself make the purchase yet. I did NOT know they were uncomfortable at first. I don’t know if I can wear uncomfortable shoes for over a year to break them in! My husband might thank you for posting this because it will make it even harder for me to spend the money on them 🙂


    • Beyond uncomfortable. (I guess I’m not going to be writing any posts sponsored by Frye any time soon, eh?)

      But it could just be my feet.

      And once you hit that sweet spot. Omigosh. You will want to wear them all the time. And I do. Even in the summer with skirts. I love them so much. I know these will work out.

      But if we are talking about the wallet here and your husband: Go to DSW. I’m sure you can find a lovely pair of boots. I just have meaty calves. And a long love affair with Frye. 😉


  22. Oh, I can relate. I hate spending money on myself and I always question if I should spend “so much” on a pair of shoes. But if you love them, wear them, get tons of use? Well dollar cost averaging is important too 🙂

    never heard of Frye boots…now I am curious 🙂


    • I figure its like writing. Or giving birth. These things aren’t easy. Or painless. But we do it. And it can feel so good after all that hard work.

      Right now, I’m at pain. 😉

      But you are right.

      I find it so hard to buy anything for myself. I almost get paralyzed. I am, however, very good at helping others spend their money. 😉


  23. Oh man, isn’t that the truth. But when it comes to my feet, I usually go for comfort. Those are some seriously cute boots though.


  24. Yes, I did.

    And I knew it was the right thing to do.

    While in Texas in 1987, I bought real Capezio (remember them) boots for $125. Still have them, they kick ass.

    Just like that picture of you up there.

    Damn worth the joy they bring me.


    • Capezio boots? I had hot pink flats in middle school. They were a zillion dollars.

      But I was smokin’.

      I can’t imagine how much Capezio boots would have cost!

      What’s with the Mrs. Pitt thing, Alexandra? Are you incognito? In witness protection? 😉 Loved your post today at AimingLow.com.


  25. Oh, Renee, I could say so much about this post. Sometimes I feel like I’m stuffing my life into those boots, bleeding heels, band-aids and all. Walking in pain and just hoping they’ll stretch, that they’ll finally fit just right. A well-worn life takes a little pain and determination. But oh so worth every single uncomfortable step.


  26. carolofthebells

    I just bought a winter jacket for under $30; perfect colour, some fake fur, covers my tush, looks great, and is machine washable. So, why are four or five organs still seizing up every few minutes (over such lavish spoiling of myself)? Pathetic! I’m afraid to tell you it only gets worse when one becomes a grandma.. Anyway, I love boots. I love your boots. I love Frye boots. I love boots on anyone, male or female. Maybe even on a spaniel, I don’t know, but I DO know I can never ever try on boots. I would line my closet floor with them, and then die from sheer guilt. Enjoy, tho’ — enjoy!!


    • Carolofthebells:

      I’m already so frugal. I have wanted to self-host my log for ver a year, and I just can’t justify it.

      Plus I’m technologically challenged.

      Thanks for the well-wishing on my new boots. Hopefully by the time I’m a grandma these suckers will be super comfortable! 😉


  27. Nah, I am a shoeaholic and I don’t regret my purchases….ever…..much. I have shoes that hurt, I don’t care they are beautiful. I have dozens of shoe stretchers! I line my shoes up and put those stretchers to good use.

    The only time I ever kinda choked up on a purchase was when I bought my custom made cowboy boots 25 years ago. At the time the were so expensive and I could hardly afford to hand over the $350 I paid for them. But oh I do still love their fabulous red color and the subtle soft feel.

    I also love Frye boots!


    • Shoe stretchers! I. Am. An. Idiot. Omigosh! Am going to get some tomorrow! Do you have any tips? Should I go a size up? More? How do I get that seam in the back to soften up?

      So it’s not just me? Fryes hurt at first, right?


      • Shoe stretchers primarily work on the front of shoes. The stretchers are mostly one size and you twist them out to stretch the shoe.

        But there are some things you can do with the seam. Can’t soften it, you can though buy the gel pads and put them over the seam so the seam doesn’t rub directly on you until it is worn in. That is what I have done.

        You can also get so leather softener. Though this takes a bit longer.


      • Shoe stretchers primarily work on the front of shoes. The stretchers are mostly one size and you twist them out to stretch the shoe.

        But there are some things you can do with the seam. Can’t soften it, you can though buy the gel pads and put them over the seam so the seam doesn’t rub directly on you until it is worn in. That is what I have done.

        You can also get so leather softener. Though this takes a bit longer.

        And yes Fryes usually hurt at first.


  28. I bought a pair of Doc Marten’s for $150. For as long as I wore them it averaged out to $10 a year. Pretty good price! 🙂 I finally decided they looked dated and sold them.


  29. When I was 15, I spent $125 of my hard earned babysitting money on a clunky pair of Doc Marten sandals. They were huge. And smelled great, like leather. And were super ugly, I just didn’t know it then. They also turned out to be supremely uncomfortable. And they never broke in. So I threw them out five years later.
    That’s a disappointing story of when I spent money on myself, LoL. Now I’m a lot wiser about how I spend my hard-earned babysitting money. 😉


  30. Those look worth the price and the pain. Smokin!


  31. —-those boots are still hot after all of these years, babe! Xx


  32. Tactical boots are much the same. I always where them for a little while before I actually use them for their intended purpose.

    LOVE a good set of gear!


  33. Well I will say those are some genuinely cool boots, but I think you could pull off a couple paper bags! You are rockin’!

    I always have a hard time spending a lot of money on clothes/shoes. I think my wedding dress was the only thing I’ve ever bought that cost more than $200. Winter coats included.

    P.S. – I’m told this Dr. Scholl’s ‘stick’ thing (looks like a glue stick) works like a dream – you just rub it on wherever you’re getting a blister. Given that when I last tried to buy it, it was sold out, I think there’s something to it…


  34. Wait a minute… Renée, you do not look old enough to have been in college in 1885… but, I’ll take your word for it. I can remember buying my daughters Frye Boots once long ago. The last few years it has been Uggs. Everyone in Friday Harbor now wears Uggs, so on our back-to-school shopping trip to the mall on the mainland, we ended up in Clark’s looking for boots to replace the Uggs. I left with a somewhat lighter wallet, but a fuller heart. My 42 yr. daughter reminded me she was taking some college classes again, and my 45 yr. old daughter reminded she was in college in 1985. I didn’t need the reminders… now my daughters will look so much more fashionable than the Ugg wearers this Winter. No fretting on my part… but I do gasp a bit when I close my eyes and hit ‘send’ on an order at the Apple Store… but, never any regrets.

    p.s. cute photo


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