• Skip to main content
  • Skip to primary sidebar
  • Skip to footer

Nina Anders

Living an Ageless Life With Style

  • About
    • Privacy Policy
    • Cookie Policy
  • EBook
  • Shop My Favorites
  • Beauty
  • Fashion
  • Lifestyle
    • Inspiration
    • Morning Musings
    • My Almost Empty Nest

Best Dresses to Wear With This Season’s Cowboy Boots

10/29/2021 · In: Fall, Over 50 Fashion

Cowboy boots and western inspired boots are having a moment.  Mind you, we are not seeing classic cowboy boots, mainly boots with subtle western inspired details, especially in chic booties and knee high boots. This season’s cowboy boot is solid color without the  decorative stitching, mixes of materials or metal touches we sometimes see in western cowboy boots.   We get the western influence through the cut of the boot, the arch at the top of the boot, a pointed toe and heel details.  The look is a gentle nod to the west, rather than a bold statement.  A great pair of boots should be on your list this season. Even so, cowboy boots can be tricky to style, especially if you don’t live in the west.  

Cowboy boots are a classic look that can be worn year around in many different ways.

Because cowboy boots are often paired with a crop top, denim shorts, skinny jeans or a mini dress, and a cowboy hat, we often think cowboy boots are the domain of the young.   It can be hard to imagine styling this type of boot in other ways—including with a dress or skirt, especially if you aren’t a country girl.  With the minimal  styling we are seeing in cowboy boots this season, paired with a simple dress, well friends, cowboy boots are a great option.  

This season’s cowboy inspired boots  have a modern twist- with angled heels, pointed toes and minimal design.  They look great styled with blue jeans, of course, but the big surprise is seeing boots styled with dresses, especially knee length or maxi dresses.  I thought we should take a look at styling cowboy boots with dresses, because, well, I love boots styled with dresses, and, well, boots and dresses together are a really great thing.

Ralph Lauen Pouch bag https://rstyle.me/+LEkHRwTKBzavkybLGGKRUg

Schutz Edwiged LeatherBootie https://rstyle.me/+aYtkq1cyV9tmzyLmsXjfNw

Julie Voss gold  Fleur De Lis sarongs https://rstyle.me/+henhymT-ENJONGe3zTScBw

JCRew Camel Sweater Dress https://rstyle.me/+InJlH-A92eCmInoPNJQqGg

J

Which dresses look best with cowboy —or cowgirl boots?

There is no perfect dress to wear with cowboy boots—because so many dresses look amazing with cowboy boots, including wedding dresses, sleeveless dresses for summer, even the little black dress can get in on the boot-scootin’ action.  This look is great with classic pairings and unexpected choices like evening and special occasion wear.

As you think about which dresses you want to pare with your great pair of cowboy boots, consider the role you want your boots to play—they can be that extra subtle detail that make an outfit interesting, or statement pieces depending on boots themselves and the dress you pair them with.  

This season’s “quiet” cowboy boots let dresses shine.  Best of all, you can wear any kind of dress and make an easy outfit—whether you are going for a casual look or sophisticated.  

Denim dress:  We are seeing denim dresses this season, especially shirtwaist styles in knee to  midi lengths.  I love this style of dress, they are so sophisticated, and slimming. Pair this dress with a brown or beige boot. Perhaps in suede—and depending on the length of the dress, you can style it with booties or knee high boots.

Denim Dress https://rstyle.me/+qz7fccZgC8wCarEmIs6QsA

Angel Eau De Parfum https://rstyle.me/+MMtNUcMxJOFuuoha5baNvA

Julie Vos Palladio earing (blue) https://rstyle.me/+PUmbZCKhGIp1_78PARbMxA

Schutz Mariana Boot Brown  https://rstyle.me/+H6u-5V0CQEB6N93ShyUb_g

The midi dress: The midi is having a moment, and is a favorite for boot wearers.  From floral dresses to sophisticated sweater dresses, this length looks amazing with boots of all kinds—especially something with interesting details, such as this season’s cowboy boots.  Floral sundresses with cowboy boots have long been a summer staple.  A personal favorite look is a maxi paired with tall boots—to me it’s a perfect outfit.

Street style:  Sophisticated street styling allows us to layer a floral skirt, an oversized sweater, paired with a denim jacket and a great pair of cowboy boots—cowboy hat optional!  What I like about street style is its eclectic mix of layers and textures.  In this case, you might look for a more decorative pair of cowboy boots—since street style allows us to go off script if we want to.

Mini dress– or shorter dresses are also being shown this season, and this is where your favorite pair of cowboy boots take center stage.  Pair this look with a leather jacket or one in denim, and you have a great casual chic outfit.

The farm chic maxi, the floral dress made of floaty fabric and ruffles is another wonderful look, especially for a western wedding or special occasion.  And while we are chatting — western dresses with long sleeves, rounded yolks, belted at the waist are also classic western looks that make for an easy outfit.  Long dresses are also great with boots.

Sweater Dresses:  This year’s maxi sweater dress looks amazing with boots, especially cowboy boots for an unexpected modern look.  Wearing interesting a simple sweater dress with black cowboy boots  is a  great piece to show off your cowboy boot outfit.  Throw on a denim jacket or an oversized blazer, and you have a great look.

Honey Bee Statment Necklace in Ruby https://rstyle.me/+dDtPbCWd3FCbhBLqTREC5Q

Jessica Simpson red  Zadie booties https://rstyle.me/+KQtOqynKG9iFmNR-AdAQpg

Good American Georgette Dress https://rstyle.me/+S7yEjLCMkDUbxCNKU08Xbw

Gucci Nail Polish https://rstyle.me/+okC-27MM1BltfO_SxYv2dw

Great Cowboy Boots to Try

Cowboy boots were originally designed for utility, and come in many different styles.  Most predominately, the boots come with several toe styles, including rounded, pointed, square and snip toe styles.  Through the years, cowboy boots have become more decorative, combining rare leathers, special stitching, fringe and medal details for special occasions—and are no longer just work boots.  The heel styles are also distinctive, and were designed for specific uses, including riding, walking and roping.  Designers often exaggerate these details to create unique and interesting styles.  The top of the boot is often rounded and sometimes features holes or handles to help pull the boots on.  

Traditional cowboy boots are mid calf height—but today tall boots often have western details-though they are most likely not considered western wear.  However, paired with a cute dress, they are a fun way to take part in western style.

When it comes to color, don’t forget to consider bright colors, and white as the make a perfect pop of color to your outfits.  When collecting boots, I always go for the classic colors and styles  first, followed by fun colors and patterns—that goes for my whole wardrobe—once you have the basics in your collection, adding bright colors, fun patterns, interesting stitching  and interesting leathers is always fun.  It’s also fun to play and put together interesting outfits—especially when you get a new pair of cowboy boots.  Remember, there is no right pair of boots, can be styled into a good look.  

So as you are looking for stylish cowgirl boots, be sure to take into account these details, which can be combined to make very stylish boots.  While cowboy boots are quite practical, we have seen that they can also be very stylish, and can add interesting detail to an otherwise basic outfit.  Further, they don’t need to be worn with westerner.  

As you can see, cowboy boots look great with all types of dresses, and there are many boot styles to consider for your collection.  Whether you love classic western boots or those with a modern twist, and no matter what style or length of dress, there is a perfect cowgirl outfit for you.  Lately, I’ve been thinking about how important it is to just have fun, experiment  and enjoy the various trends that capture your imagination.  

Read more posts about Dresses, Jeans and Everything You Need to Know About Styling Jeans and Boots

By: Nina · In: Fall, Over 50 Fashion

About Nina

Sharing A Journey is an award winning blog for women "of a certain age" who love life and style with a little inspiration mixed in. The blog and it's author Nina Anders has been featured in notable publications including Forbes, Next Avenue, Thrive Global and Parade. Photos by RSEsteyphotography Let's do midlife together!

you’ll also love

Early Fall Wardrobe Hacks: 8 Ways to Start Fall Now
Closet Clear Out: Selling Your Clothes
Six Easy Fashion Tweaks featured by top Tampa over 50 fashion blog, Sharing a Journey.Six Easy Beauty & Fashion Tweaks

Join the List

Stay up to date & receive the latest posts in your inbox.

Reader Interactions

Leave a Reply Cancel reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.

Next Post >

Is The Dyson AirWrap Worth the Money?

Primary Sidebar

Meet Nina Anders

Meet Nina Anders
hello!

Welcome to Sharing a Journey! If you love modern classic fashion, videos about beauty and skin care with a little inspiration and lifestyle mixed in, you are in the right place! Grab a cup of coffee, and take a look around.

Read More

Connect

Categories

  • Beauty
  • Fashion
  • Inspiration
  • Lifestyle

Purchase A Copy of Graceful Transitions Here

Advertise

SiteGround Ad

Disclaimer

This site uses affiliated links in some of it’s posts.  Posts with affiliated links will be noted.  Sharing A Journey also receives gifted items provided for review.  When we have received an item for review it will be noted in the post.  As always, our opinions are our own.    Please stop by my About Page to read more about our policies such as copyright, disclaimers, and collaborations. Please Click Here for Our Privacy Policy

Buy Me A Coffee?

https://buymeacoffee.com/ninaanderssharingajourney

Follow Along

@sharing_a_journey

Nina Anders | Sharing a Journey

sharing_a_journey

Life and Style Blog | YouTube Channel

2025 is my year for a Glo Up starting with my skin 2025 is my year for a Glo Up starting with my skin care routine. I just started using the ZIIP Halo on my 65 year old skin.  Cant wait to see the results. #livingmybestlife #over60andfabulous #over50model #over65skincare @ziipbeauty
This week’s mini adventures had us in one of my This week’s mini adventures had us in one of my favorite spots-Dunedin Florida. We went for coffee and croissants at @dunedincoffeecompany where they have amazing coffee and a real in house bakery. Every so often the baker comes through with delicious creations right from the ovens. We went for some design inspiration @lrhome their shop never disappoints then on to the book shop. That made us hungry so we had to go to  @casatinas. How could you not?#livingmybestlife #over60andfabulous #over50womenoninstagram #over50style #outfitoftheday #over50model
I've been making a point to spend a lot less time I've been making a point to spend a lot less time on screens this year. It's been amazing how much free time I have to enjoy new hobbies and spending time with friends and family. I even tried my hand at painting with a Time For Art kit and actually made this sweet dolphin painting. I was surprised how easy it was even for someone like me who has very little painting experience. I loved how the kits came with everything I needed to make the painting, and I when I needed help, I watched a video on the Time for Art website. I thought it would be fun to host some friends for a girls painting night, invitations are in the mail--plus it would make a perfect gift. Be sure to check out @timeforartlive--I will link all their info in my link tree.
For the next 65 Days I am challenging myself to ch For the next 65 Days I am challenging myself to change a few bad habits and prioritize health, friendships and activities that enhance happiness and creativity.  I am looking forward to going into 65 and beyond healthier and happier than ever before. I hope you’ll join me over the next 65 days by choosing something you’d like to improve or a habit you’d like to break and see where it leads. #over50womenoninstagram #over60andfabulous #livingmybestlife
Instagram post 18020842631137506 Instagram post 18020842631137506
Instagram post 17901405167968170 Instagram post 17901405167968170
Load More... Follow on Instagram

Footer

On the Blog

  • Beauty
  • Fashion
  • Inspiration
  • Lifestyle

Info

  • About Nina Anders
  • EBook
  • Shop
  • Work with Me

stay in the know

Copyright © 2025 · Theme by 17th Avenue

We use cookies on our website to give you the most relevant experience by remembering your preferences and repeat visits. By clicking “Accept All”, you consent to the use of ALL the cookies. However, you may visit "Cookie Settings" to provide a controlled consent.
Cookie SettingsAccept All
Manage consent

Privacy Overview

This website uses cookies to improve your experience while you navigate through the website. Out of these, the cookies that are categorized as necessary are stored on your browser as they are essential for the working of basic functionalities of the website. We also use third-party cookies that help us analyze and understand how you use this website. These cookies will be stored in your browser only with your consent. You also have the option to opt-out of these cookies. But opting out of some of these cookies may affect your browsing experience.
Necessary
Always Enabled
Necessary cookies are absolutely essential for the website to function properly. These cookies ensure basic functionalities and security features of the website, anonymously.
CookieDurationDescription
cookielawinfo-checkbox-analytics11 monthsThis cookie is set by GDPR Cookie Consent plugin. The cookie is used to store the user consent for the cookies in the category "Analytics".
cookielawinfo-checkbox-functional11 monthsThe cookie is set by GDPR cookie consent to record the user consent for the cookies in the category "Functional".
cookielawinfo-checkbox-necessary11 monthsThis cookie is set by GDPR Cookie Consent plugin. The cookies is used to store the user consent for the cookies in the category "Necessary".
cookielawinfo-checkbox-others11 monthsThis cookie is set by GDPR Cookie Consent plugin. The cookie is used to store the user consent for the cookies in the category "Other.
cookielawinfo-checkbox-performance11 monthsThis cookie is set by GDPR Cookie Consent plugin. The cookie is used to store the user consent for the cookies in the category "Performance".
viewed_cookie_policy11 monthsThe cookie is set by the GDPR Cookie Consent plugin and is used to store whether or not user has consented to the use of cookies. It does not store any personal data.
Functional
Functional cookies help to perform certain functionalities like sharing the content of the website on social media platforms, collect feedbacks, and other third-party features.
Performance
Performance cookies are used to understand and analyze the key performance indexes of the website which helps in delivering a better user experience for the visitors.
Analytics
Analytical cookies are used to understand how visitors interact with the website. These cookies help provide information on metrics the number of visitors, bounce rate, traffic source, etc.
Advertisement
Advertisement cookies are used to provide visitors with relevant ads and marketing campaigns. These cookies track visitors across websites and collect information to provide customized ads.
Others
Other uncategorized cookies are those that are being analyzed and have not been classified into a category as yet.
SAVE & ACCEPT