Chessie’s waffle: riding boots

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When he was three years old, my son loved a particular kind of yogurt, the name of which escapes my memory.  What I do remember is that one day we went to the grocery store and found the yogurt container had a new look.  Sure, the new packaging was nicer, but Will wanted nothing to do with it.  He just wanted the old container back.

What does yogurt have to do with a dilemma about boots?  Well, I empathize with Chessie’s predicament — it can be annoying when you really like a product and then the company goes ahead and changes its’ look and style.  What was wrong with it the way it was before? you ask yourself.  And why didn’t I buy three of them when I had the chance?  Chessie explains:

About four years ago I bought a pair of brown Born brand riding boots.  I love them and I’ve pretty much worn them every weather appropriate day since.  As a result, they are on their last legs and I need to replace them with another pair.  The problem is, the style, “the Yvette,” has been changed some time in the past four years and I just don’t dig the new look as much as the old. So…now my boot choices are wide open and it’s overwhelming me. I’m willing to pay a little more for the exact right pair of boots because I know I’ll get a good wear to cost ratio if I pick well. I’m having a hard time though.

Here are the three boots Chessie is choosing between:

1.Frye’s Melissa Button boots in Cognac
riding boots, tall boots, leather boots, women's footwear, boots, fashion, fashion dilemma

2. Frye’s Paige Tall Riding boots in Cognac
Frye Paige Tall Riding Boot

3. Very Volatile’s Hennessey Riding Boot in light brown
Very Volatile's Hennesy Riding Boot

Chessie has some great choices. Which boots do you think she should buy?

Do you have a hard time choosing shoes and boots? Are you struggling with paint colors? Whatever you are waffling about, click on the button below to send me a waffle and get help.

4 responses

  1. I chose the buttons but the Hennesseys are also a close second for me. I’m a decisive “NO!!” on the suede…not at all the same feel. Re: the price, I still have (and wear) a pair of tall boots I bought 15 years ago…boots are an investment! Unless they cost as much as your mortgage, I say it’s okay.

  2. The boot waffler herself here. I love the Melissa Button boots too, but is it possible to justify the cost? Even if you wear them a lot? Thoughts?

  3. The button on the Button boots gives them a little oomph without looking too embellished. Hennessey is a very close second, but Button all the way 🙂