My thumb hovered over “add to cart.”

I’d been in the market for a pair of Chelsea boots that excited me for well over a year, and I’d just found the perfect pair.

Classic. Made for the long haul. Sleek, but also a little edgy. Equally appropriate for drinks in a ritzy boutique hotel bar AND tromping around an outdoor flea market on a foggy Sunday morning.

(We don’t need to talk about how I only ever go to Target and the dog park, ok?)

Plus, they were designed especially for wet, cool weather, meaning I’d actually be able to wear them on stormy days.

The oxblood shade — a deep, mysterious burgundy color that managed to look both black and deep brown at once — immediately made my heart go, “Yesss.”

“Ugh, but do I really want to spend that much?” I kept asking myself.

$189. A perfectly reasonable price for a pair of leather boots made to last years. Not extravagant. Not over-the-top.

Then I glanced over at my trusty flip-flops and realized I’ve been wearing them since the year of our gourd TWO THOUSAND TWELVE.

Oh. Um, okay. 

And my last pair of Chelsea boots? I bought them in 2004 and finally parted with them in… 2019? 😅

Well then. I guess it’s fair to conclude that, based on my past behavior, if I’m going to spend money on a staple piece, I’ll wear it ‘til it falls apart.

So, clearly, I didn’t need to be going all Scrooge McDuck over a pair of versatile, mid-range boots when chances are high I’ll get literal years of wear out of them.


I’m not alone, either (probably). Humans are complex creatures, and we weigh a LOT of thoughts and feelings when it comes to pricing and purchases.

Things like:

  • Do I want it?
  • Do I need it?
  • Do I like it?
  • Does it have the features I want/need?
  • Do I want to spend this amount?
  • Is this a good choice for me?
  • Am I going to feel good in this?
  • Is this purchase practical? 
  • Plus, ya know, a few hundred weird money beliefs that may or may not be organically your own (Anyone else grow up with accomplished yet v frugal parents who always commented on how expensive things are? 😅)

Pricing is subjective. What feels like a bargain for one person might feel like an impossible stretch for another. One person’s “too expensive” might be another person’s “just right.”

And hey, like I realized with my boot shopping saga, while sometimes something might *seem* like a steep price to pay at first glance, it might turn out to be very reasonable — or even wildly economical — when you factor in the value you’re really getting. 

(Yup, copy can totally be one of those things!)

So I bought the boots. They’re even more beautiful than I expected. Yup, totally worth the money. Plus, I am SO EXCITED that I don’t just get to have warm, dry feet this winter — I get to look and feel great, too.

Is there anything you’ve purchased — in life OR in work — that initially made you go “omg, yikes, that seems like a lot” but now you’re like, “eff yes, that was money well-spent?”