So You Think You Know How to Wear Cowboy Boots

Cowboy boots are fun to wear, but I recently discovered I’ve been wearing them wrong—all wrong. Fortunately, help is on the way. Some of the top designers including Calvin Klein and Fendi are about to send cowboy boots down the runway this spring and you know what that means; our sacred footwear is about to get a makeover.    

To keep you from being out-of-step, here are some tips from fashion experts:  

  • Don’t go for the costume-y look. If you’re wearing boots, avoid cowboy hats, ponchos, spurs, prairie dresses and overalls or you’ll end up looking ready for Halloween.
  • Leave the accessories at home. (I think this means don’t wear your diamonds.)
  • Avoid fringes and sequins (ruffled skirts, okay)
  • You can’t go wrong with jeans (not the faded ones) and turtlenecks. If you’re brave or  immune to stares, you can even wear boots with shorts.
  • Pair cowboy boots with animal prints.

If you’ve been wearing your boots all wrong, chances are the same can be said for the guys in your life.  According to fashion pundits, men should adhere to the following guidelines unless working on the range:

  • Avoid dressing like Woody in Toy Story. Ditch the bolo tie and chaps.
  • Forget the spurs (unless you’re playing a bad guy in a movie).
  • Hats are okay if you going to a rodeo or rounding up cattle. Otherwise, leave at home.
  • Avoid light colored jeans. Dark fitted jeans are best paired with cowboy boots.
  • If you’re wearing a tux, only black cowboy boots will do (polished to a shine).

Men, if this is too much for you, don’t despair.  Everyone loves Woody.  As for the rest of us, Happy Halloween.

What is the best or worst fashion advice you ever got?

 

What happens when four mail-order brides get cold feet?

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Margaret Brownley
Margaret has published more than 46 books and is a N.Y. Times Bestselling author and two-time Romance Writers of America Rita Finalist. She writes historical novels set--where else?--in the Old West! She has written for a day time soap and is currently working on a new series. Not bad for someone who flunked 8th grade English. Just don't ask her to diagram a sentence.
Updated: March 19, 2020 — 10:46 am

39 Comments

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  1. Good morning Margaret. Your blog had me cracking up. I’m just a simple cowgirl from Texas, but reside in Kansas due to my job, I have been wearing boots all my life. From the time I was a little girl until now, I’m just a Jean, cowboy boots wearing girl. I do not like the fashioned boots, no sequins for this girl. My boots I work in everyday. Same kind you would find on a rancher, feedlot employee, or calf roper. I laugh when I see people where attire that you can tell they just bought and dress up, it’s so fake looking, but to each their own. Thanks for the fun blog.

    1. HI Tonya,
      I wondered how this would go over with the jean, cowboy boots wearing guys and gals. Thank you for sharing!

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    Omgoodness. Texan here and this cowboy boot advice was obviously written by the New York fashion industry. First, dark Jean’s are usually only worn with boots in Texas when you have a new pair of Wranglers. Cowboy hats are okay anytime you’ve put on your boots. Dressing like Woody will get you stared at even in Texas though. If your a little, or a lot, bow legged, dusty, have your spurs and cowboy hat on and your boots are very worn, you can have those chaps on too. Pfft to this cowboy boot advice. Lol

    1. Hi Stephanie, thank you for setting the record straight about cowboy hats. Cowboy boots and hats just seem to go together. Pfft is right!

  3. Someone told me I should were this dress once. It looked terrible on me. I like the responses to how to were boots. I feel you should do what feels right.

    1. Debra, I absolutely agree. Which is why I do wear sequins! LOL

  4. Ha my daddy once told me my makeup looked like I was painted up to go on the warpath. My mom once made me wear this hideous pair of striped jeans to school they were purple, gold, burgundy and cream color strips I was in 6 th grade and wouldn’t you know we had a tornado drill that day so I was sitting in the hall where the whole 6 th graders were and I was in tears because the laughs I got at those hideous pants

    1. Avatar

      Oh Glenda we all have those terrible clothes our mom dressed us in stories. Thank God we weren’t in the cell phone generation!!!

    2. Hi Glenda, I had to laugh at the warpath comment. I recall my daughter going through that stage. I probably did, too. Ugh, the pants.

  5. My mom always says if you wear anything with stripes, make sure they are vertical stripes because they make you look thinner! And I love wearing my cowboy boots with my jean skirts!

  6. Hi Elizabeth, yes, I heard that same advice about stripes. I don’t think you can go wrong with jean skirts and cowboy boots!

  7. Hi Margaret …. I loved your blog. I’ve been wanting to buy a pair of boots for a long time. This little voice whispers to me that I’m too old. Well, am I? Maybe not! My husband bought a pair of nice cowboy boots in Williams, Arizona when we traveled to the Grand Canyon. One thing is for sure … I better do it sooner than later. If you get my drift.

    1. Oh, Kathy, you’re never too old for cowboy boots–never! Now go and buy yourself a pair. You’ll feel better.

  8. I am not a boot type of girl but I do love the look of boots on some people. I do know when my nephew got married the girl he married wore cowboy boots with her wedding dress and I thought that was pretty cool.

    1. Hi Quilt Lady, boots with a wedding dress sounds pretty cool to me, too. I wonder what the fashion folks would have to say about that.

  9. My Dad always said you were not ready to ride a horse if you weren’t wearing your boots!!

  10. Hi Theresa, your dad’s a very wise man.

  11. Your blog made me laugh! Of course the designers are going to tell us what to wear with their new high priced boots! I’ll take a guy in faded jeans and boots. I’ve never been one to follow “fashiion” and don’t intend to start now!

    1. Good for you, Trudy! I think we should wear what feels right for us.

  12. I have never followed the fashion trend.

    1. Hi Kim,
      You, Trudy and I have something in common. I’d rather be a trendsetter than a follower.

  13. Thank you, Margaret. This is great advice! I live on the East Coast, and I’ve always been a little self-conscious about wearing cowgirl boots, although I loved wearing them when I was country line dancing back when it was all the rage! I think I’m good to go with them now if I follow these tips!

    1. Sharon, you really must give boots another try. They’re so much fun to wear.

  14. Welcome Margaret, I’m sorry but this post made me laugh. I suppose I have really not cared what others thought about how I wore my boots and with what. LOL I have always loved wearing them with jeans, skirts and skorts. Same with my mom. We had a boot store in the dessert that made boots special and the owner would color what parts of them that we wanted. I was able to get boots for dressing up with pink flowers. Ohhh but I felt so pretty. I have seen men dressed up in suits with black and brown boots. And yes the black boots I think look so much better.

    1. Lori, I’m drooling. Boots with pink flowers. Wow. Fancy boots are the best.

  15. I was raised in Texas, now living in Kentucky. I love cowboy boots, but I never could pull off the look. Even as a kid, my Papaw was so proud to buy me this pair of pink cowboy boots for his “little cowgirl”. I loved them and I wore them, but I don’t think they were ever “fashionable”. lol Maybe someday I’ll get the nerve to try them again!

    1. Hi Holly, according to those in the know, cowboy boots are back in vogue, so you might want to give them another whirl.

  16. What a darling post, Margaret, really enjoyed it! Nice to see some light-hearted topic in a time like this. And a lot of good info, too.

    1. Thank you, Hebby. We need some light-hearted fun, right? Take care.

  17. I still regret that time I let my mom my hair in Middle School. For the record, I rocked my cowboy boots when I wore them with my wedding dress at my reception!

    1. My mom crimp my hair

    2. Hi Carrie, I read somewhere that crimped hair is back. Some people can carry that look off. Not me. Love that you wore cowboy boots at your reception. Way to go, girl!

  18. A fun post…but I think it is a designer’s advice. I guess if your a gal going dancing you might not want to wear a cowboy hat with boots but I agree with Stephanie, cowboy hats and boots go together.No faded jeans? They must mean the kind you buy already faded. Jeans faded from wear and washing are definitely acceptable with boots. At our oldest daughter’s wedding my husband didn’t wear his boots but he did wear his hat at the outdoor reception. At our youngest daughter’s wedding he said he was going to be comfortable and wore his boots.

    1. Hi Alice, good for your husband! I hope he wore his hat with the boots.

  19. Margaret, Thank you for the fun post! I enjoy wearing by boots with a long denim dress.

    1. Hi Caryl, sounds great. I wear mine with a long denim skirt.

  20. I always wear my boots with Jeans and only with Jeans. I do love the way they look with jean skirts also. Thank you for this good advice.

  21. I guess the advice is great for those who have never or will never venture into the real world. When we lived on Colorado and California far from the fashion districts, we saw just about every one of the don’t listed above. Cowboy/cowgirl boots are as common as sandals and sneakers and worn with just about anything. Even a hard working cowboy with beat up boots will have a good polished pair for a special night out or occasion.
    The only real fashion advice I got was from my mother in law. Not really about clothing, but hair. My hair was always since getting married. When I was in my 40’s she keep saying I needed to get it cut short because people my age shouldn’t wear long hair. 30 years later, I can still braid it.

  22. Avatar

    I was gifted with a pink, knit poncho by my aunt for my birthday. NEVER wore it. I also never wore: Go Go boots, paisley prints, animal fur, animal prints, black and white striped tops (like baseball umpires). I didn’t like the really wide bell bottom pants and jeans.

    I grew up in the Midwest. People didn’t wear cowboy boots or cowboy hats there.

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