A year ago I wanted a pair of ankle-height engineer boots.

I decided the Engineer 8R was the right look, and I found a size 7 pair at Yoox for around $100, the only size they had. I bought them gleefully, wore them once, and realized that the boot hits my instep in an incredibly painful way. And they're a tiny bit too small everywhere.

(I'm usually a size 6.5 but often 7 for boots. But my old Frye-imitation harness boots were 7.5 and perfect.)

So there they sat in my closet for a year, unworn. I pulled them out again last week and they weren't as bad as I remembered, but I had to change shoes after a few hours. I wonder if I could get them stretched, though they're lined with a thick synthetic fabric without much give.

Meanwhile, last month a local store had a closeout ($100) on their Sutro boots made in the same Mexican factory as Frye. 6.5 was too tight, they were out of 7, and the 7.5 felt comfortable. I wore them around the store with a thick pair of socks -- no problem. Bought them, wore them, and... pain, again. The ankle area cut into my anklebone badly and they really are too long.

So, here I am with two pairs of less-than-ideal boots. Then I stopped by Crossroads today and someone is selling the Frye Veronica short boots for $55. Size 6.5 and these really do fit me perfectly! They're definitely used, but with plenty of life left.

So what do I do? Sell the Sutros, regardless, I think. But should I spring for the Veronicas? And I can't help wondering if I should try the Engineer 8R in a 7.5, instead.

I can't decide which look I prefer, either. Opinions? The Engineer 8R is shorter and I think more flattering on my short legs and more distinctive to me. I'm often a passenger on a motorcycle and they boots would be serious protection, so that's one side advantage. I do think I prefer them, but the Veronica boots are going to be more comfortable and lighter, regardless.

Analyzing my failures here -- one was chasing after discounts rather than finding the perfect thing and paying full price. But on the other hand, I've bought full-price shoes I thought were perfect that ended up unwearable. It's just so hard for me to know. I shudder to think of how much money I've spent on shoes I had to pass on immediately. Am I the only one?

Would buying the Veronicas be throwing good money after bad?

Edit: I wore my Frye Engineers today. I think they're stretching out. They're not as painful over the top of my foot, though still bad after a few hours. Worn here with R13 relaxed jeans. I do think I like the height of these compared to the Veronicas but maybe either would be good.
Photo 1: Veronica
Photo 2&3: WIW: thrifted Club Monaco top, R13 relaxed skinnies, Frye Engineer boots.