Cowgirl Boots – How to Wear Them and Not Look Ridiculous

Hi Deborah,

I am 47 years old and always liked cowgirl boots but never had the courage to wear them. Now, at this point in my life I have a craving for them. I don’t know if I am having a midlife crisis or something of that sort, but I’d like to try them.

I am in no way planning to wear cowgirl boots to a restaurant or work. I just want to wear them to go to street festivals during the Fall or Ferias in Spring, and I want to wear them with class and the finesse appropriate for my age. Can you give me suggestions for how to style them?


Hi Anne,

I completely understand how you feel. You just want to have a little fun and get in on the cowgirl theme of these events without looking like you are wearing a costume. So here’s how to do it.


1. Try a Denim Shirtdress

Chambray or denim shirtdresses are very popular at the moment and look cute in the summer with cowgirl boots. The only thing is you need to find one long enough, and that is going to vary depending on the make. This one above might be too short for some gals.

If that is the case, just throw on a pair of black leggings underneath your shirtdress. Since the dress is so plain and classic, you can have a bit of fun with your accessories. A fringe bag is casual and playful. Some beaded leather jewelry and rustic native earrings blend in with the vibe


2. Wear a Checkered Shirt 

If you’re a blue jeans and checkered shirt kind of gal, that’s fine too. The key is to keep things polished and pulled together. Keep your shirt sporty and crisp by rolling up your sleeves into a neat cuff, add some pretty Southwest jewelry.

Skinny jeans look modern, but bootcut is fine too. They’re a classic. Don’t forget to wrap up your look in a stand-out belt. It’s little details like this that make your western look fab and not frumpy.

Anne, enjoy and have fun!

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6 thoughts on “Cowgirl Boots – How to Wear Them and Not Look Ridiculous

  1. Natural fabrics like cotton or silk. I wash silk never dry clean it. Polyester is the worst for night sweats. Not too baggy. And none of those ugly slippers. An old cashmere sweater in winter is actually wonderful and for those of you who think wow too much investment in sleeptime clothing, i am a treasure hunter and thrift stores and the washer/drier combo gives me ultimate luxury at a reasonable price.

  2. I snap up EVERY silky shortie set or gown I find, nowadays, that fits, because it seems to me as though the only things people are selling are dull-looking pyjama pants and tees. I don’t know how other people wear these, because if it crawls around my legs or binds as I try to turn in my sleep I have a really bad night. I happily have a fairly good stock of spaghetti strap gowns and a couple of short top over thong sets in the house. I guess when those wear out, I’ll have to resort to my husband’s t shirts or sleeping in the nude all night. What’s wrong with designing nice gowns with filmy robes any more???

    1. Hi Linda, Yes! I live in a cold climate and even in the summer feel chilly, so for years I liked to wear p.j.’s. However, these days with night sweats, I am finding a little nighty to be super duper comfy!! Good suggestions!

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