Ask Allie: How to Style Cowboy Boots

I have a cowgirl ball to attend soon. I live in Texas and think I may need to add cowboy boots to my wardrobe. However my style is more classic and ladylike (think Talbots, Ann Taylor) and have a hard time doing “cowboy”. Can you recommend something for this cowgirl ball plus how to add cowboy boots to my wardrobe going forward?

Up north, a ball usually means black tie. However I’ve noticed further south ball can mean a multitude of things. Thanks to your information, I was able to confirm that the type of ball you’re attending is more casual than you’d expect. Think sundresses, jeans with cute tops, denim shirts with skirts. It would be completely acceptable to choose a dress like this one from Talbots, this one from Boden, or this one from Ann Taylor or something already residing in your closet.  If you wish to have it look more “cowgirl” consider topping it with a denim jacket, but honestly from the looks of the pictures while some will go all-out with cowgirl regalia, most seem to wear clothing you could find at your favorite mall retailer, just paired with boots.

When you’re new to an area it can be pretty intimidating to attend such events; thanks to social media it’s easy to search for photos or articles about previous years of the event or similar functions. Even if you don’t have a Twitter account, if the event you are attending has a hashtag, enter it into the search function at the top of twitter.com and all the tweets using that hashtag will show up. Some of them may include photos showing what attendees wore. If there isn’t a specific hashtag, enter the name of the event and likely tweets will show up. Instagram isn’t as easy to search if you don’t have an account; visit http://websta.me/search and put in the hashtag (or try making the event’s name into a hashtag like #XYZcowgirlball) and you should find relevant photos. I admit I do this quite often; it’s a great way to get a feel not just for the attire but the feel of the function and you can be prepared.

As for cowboy boots, it’s actually not that difficult to incorporate them into a classic wardrobe. I’d recommend your first pair to be a single color, simple in design, and the leather color that best matches your current wardrobe (black or brown). There’s no need to go out and buy a whole wardrobe of chambray, eyelet, and bandana prints to wear such pieces. Go slow, and incorporate them at first in the same manner you would a tall pair of boots. Here’s some ideas to get your creative juices flowing:

How to style cowboy boots

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Here, I took a classic look of narrow jeans and a crisp white shirt which would often be styled with riding boots, and switched them out for cowboy boots. The white shirt could be topped with a blazer or cardigan and easily replaced with a simple knit top. The point is to show you can easily pair cowboy boots with your regular casual or business casual attire. There’s no need to change your normal accessories because you changed your boots; go ahead and wear your pearls, your sparkly statement necklaces, your delicate chains. The same holds true for your bag; wear a style and shape that fits your personality first.

how to style cowboy boots

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A cowboy boot looks great with a skirt with some volume, but that doesn’t mean you need to look like a square dancer. Fit and flare, pleats, gathers, and a-lines nicely balance the weight of a cowboy boot. Like me, you likely already own pieces like this in your wardrobe and paired them before with sandals or nude pumps. A switch to cowboy boots won’t look unusual; if you feel the cowboy boots are too rugged for your look up the femininity quota with a pastel bag and floral necklace. As an FYI, this look is an easy one to dress up for an event; switch out the skirt for a full length version, change the shirt into a crisp white one (or keep the denim if appropriate to the occasion) and have a super sparkly necklace and you’re evening-ready.

how to style cowboy boots

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A boot also looks great with a looser shift dress. If you choose it in a drapey fabric like silk or rayon it won’t look too boxy. Even add a longer or heavier necklace to hold down the dress and reduce volume on top. Again, no need to buy a whole new wardrobe of bags and necklaces to accommodate your boots.

how to style cowboy boots

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I must say this look was inspired by a woman I saw several years ago in the city. She had a similar outfit but in all greys with some well-worn brown cowboy boots when one would usually wear riding boots. The look was so chic and looked so right. A midi skirt is a great pairing for cowboy boots; the soft gathering gives a bit of volume to balance the footwear without overwhelming the frame. Keeping all the colors similar helps the boots blend into the look. A necklace with a natural element to it helps the boots look purposeful.

Do you wear cowboy boots? What are your recommendations for styling them?

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22 Comments

  1. Clare
    April 7, 2015 / 11:29 am

    Frye boots. I think they run small (I wear a 8.5W or 39 Euro and am wearing Frye 9.5). They look tough, with real leather, and have enough heft that you don’t look silly, but also have a solid rep with fashionistas.

  2. B.A.
    April 2, 2015 / 1:33 pm

    Are there links for the boots shown in the outfit pictures or did I just miss them? I’ve been thinking of buying brown cowboy boots and would love to check those out.

  3. Caitlin
    March 31, 2015 / 10:17 pm

    Love all of this but especially that skirt! Xo

  4. Sallie Stephens
    March 31, 2015 / 2:53 pm

    I actually have my beloved (red!) cowboy boots on today…paired with a black maxi skirt, graphic tee and jean jacket. I LOVE to wear mine and I live in the midwest. I also will pair them with a shorter Ann Taylor skirt, white blouse and black sweater. And tights. In the summer I will wear them with a sundress and a crisp white jean jacket. And I adore that floral skirt you featured! Gorgeous.

  5. Janki
    March 31, 2015 / 1:27 pm

    THANK YOU! You were so sweet to feature my question (I nearly squealed when I checked the site while at work). I now know exactly what to wear to the event and how to make sure these boots get some use during the year.

    Like a poster below said, I also live in Austin and see cowboy boots on others but didn’t think I could pull them off. I’m going to start with this ball and then add them in baby steps. I’ll send you a picture of the event too.

  6. Marcia Brinkley
    March 31, 2015 / 12:51 pm

    I lived in Austin for 10 years and saw cowboy boots everywhere, even on lawyers in court. I didn’t wear them because they just didn’t look good on my very short and chubby legs. Now that I’ve read your post, though, I’m dying to buy cowboy boots just to wear when I feel like it, even though I live in Hawaii now. Any good sources for wide calf cowboy boots for short people? The ones I see online seem like they would come up to my kneecaps.

    • April 1, 2015 / 11:00 am

      My go to for wide calf boots is http://www.widewidths.com/ and DUO boots, but neither seem to have cowboy boots… now. But Wide Widths has in the past and I hope they do again in the future! With DUO, even if they don’t have cowboy, they do categorize boots by short legs and have custom width calves.

  7. Elin Olson Glenn
    March 31, 2015 / 11:54 am

    This is a great, and timely post! My hubby surprised me with a pair of deep plum Frye boots for Christmas and I was just lamenting the fact that I would have to pack them up until next fall. However, they are somewhere between riding boot and cowboy boot (the style is the Elena), so perhaps I can wear them a little longer this season!

  8. Grace Mitchell
    March 31, 2015 / 9:43 am

    I’m a big fan of cowboy boots, and I love all of these looks. I will pretty much wear mine with anything. For spring and summer, I love them with wide skirts, maxis, sundresses, and even shorts. My advice is to think of them as a neutral.

  9. March 31, 2015 / 9:26 am

    I’m not a cowboy-boot lover, but oh, that yellow full-length skirt! Divine.

    • March 31, 2015 / 9:47 am

      I know isn’t it to die for? I wish I had an event to wear one of Shabby Apple’s long skirts!!

  10. Aimee
    March 31, 2015 / 9:15 am

    I also live in Texas and would love to try cowboy boots with dresses because I love the look. I am forever trying to think of ways to hide my spider veins and this would be a great way to do it. Summer is always a hard time. But, at 47, has this shipped sailed already? I do look young for my age but don’t want to do anything that will make me seem like I’m trying too hard. Thoughts?

    • March 31, 2015 / 9:49 am

      I don’t think so! I’d say start simple with an outfit similar to the first or third and see how you feel. Wear them as you would riding boots, which is an ageless accessory. Choose a neutral style at first, but accessories are a great way to add personality to a wardrobe no matter your age. In fact, I think age is a benefit when it comes to statement accessories – we wear them instead of them wearing us!

  11. Jessica
    March 31, 2015 / 8:09 am

    Thanks for this post Allie! I own a pair of cowboy boots but admit they’re gathering dust, especially outside of summer when I can wear them with bright skirts.

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