What to wear with tall glossy boots

What to wear with tall glossy boots? Well, welcome to October! This is the month where we get to ask these kinds of questions. 🙂 Yesterday was sunny and today it’s all rain. I don’t mind, though. I find the rain comforting at this point in the year, and welcome the chance to be cozy. This is about the time when our boots and rain jackets go into almost daily use. I welcome a heavy rain because it gives me an excuse to wear my favorite boots!

I first saw these Women’s Hunter Original High Gloss Boots when we were in London five years ago. It seemed like all the fashionable women had them. And black was the only color I saw. Some were the tall glossy boots and some were short or matte. As soon as we got home from our trip, I looked into buying them. I quickly discovered they’d be the most expensive rain boots I’d ever considered! Was it worth it to pay over $100 for a pair of boots that would splash in puddles? I thought about it for months and was on the lookout for a sale. Different colors would go on sale from time to time, but not the shiny black ones I coveted. I finally bit the bullet and just ordered them.

For the first year, I kept track of how many times I wore them and calculated the cost per wear. I’ve now worn them dozens of times and my cost per wear decreases every time. I think it was a worthy splurge!

But anyway, what to wear with tall glossy boots like these? My go-to pants are skinny jeans like in the picture above, or a thicker legging. I find that a fitted pant tucks inside the boot well and is the most comfortable choice. Tighter pants also show off the beautiful high gloss boot! 😉 If you are in the market for some new leggings this fall, check out my review of these great $10 leggings from Amazon. They come in a ton of colors and plus sizes, too. Did I mention they are just $10? So really, you can’t go wrong. I talked them up to my mom and she bought a pair as well. She says hers are super soft and comfy, just like mine. She is 5’9″ and I am 6′ and they fit both of us. The leggings are very stretchy.