Winterwear: Classic Riding Boots

Cole Haan Oleanna Boot in brown compared to Madewell's Archive Boot in black

Flat riding boots are my winter footwear of choice. They are perennially chic and totally classic, whether worn over skinny jeans or under thick tights and a skirt. Plus, they keep my feet warm and add another layer of protection from the elements. I already own a few pairs of riding boots, but I have an insatiable appetite for more. I’d really like to invest in a high quality, not-too-trendy pair that would last for years. 

These classic riding boots by Cole Haan in brown and Madewell in black caught my eye this season with their subtle stitching details and durable good looks. I’m particularly enamored with the Oleanna boots by Cole Haan. It was love at first sight! I even dragged my friends into the Cole Haan store in Kansas City so I could say hello to these beauties. 

However classic these boots may be, I can’t possibly justify spending $450 on one pair. “But I’ll wear them forever!” I say to myself, as reality taps me on the head and reminds me that I don’t have $450 to spare (this is the story of my life). Sigh.

Not one to give up easily, I’m holding out hope that these boots will go on sale after Christmas. I’m crossing my fingers that I’ll be able to find them for at least half off so I can buy them with leftover Christmas money. I’m not leaving this to chance, though–I have sale alerts set up so if they go on sale, I will know pronto and snatch them up!

Later this week, I’ll be back to share my shopping strategy for these boots and for all the other drool-worthy items on my wish list. Stay tuned!

  • Comments

    1. Hali says

      You might want to look at the Venice Field Boots by Mountain Horse ($199) or the Westchester Dress Boots by Ariat ($379). Both are actual riding boots that are quite stylish.

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