I Used to Cringe at Cowboy Boots, But These 18 Outfit Ideas Changed My Mind

Confession time. I used to loathe cowboy boots. I know that's a strong feeling about shoes—alas, I did. Part of my anti-cowboy-boot disposition can be attributed to good-old teenage angst. Cowboy boots represented my years of growing up in the West when I felt called to live out my life in bigger cities like New York, London, and Paris. But the other part of my distaste for these boots had to do with how they're styled. I should preface this by saying that I do not believe there's a "right" or "wrong" way to wear anything—fashion is all about exploring what feels good for you. This particular boot style, however, just rubs me the wrong way. As snobbish as it may sound, I've concluded over the years that there are ways in which cowboy boots should and should not be worn. It's an opinion I reached only after years of living away from my hometown.

I've realized, though, that I don't hate these boots. I just needed to find a way to style them that worked for me. It was only after stumbling upon stylish designer versions and unearthing different ways to wear them that I came around to the idea of cowboy boots. In an effort to share what I've found from that self-reflective journey, I've rounded up outfit ideas to show what to wear with cowboy boots. Plus, I've included items to embrace and avoid when styling them. While you should always wear what makes you feel your best, I've found that these styling rules helped me transform my feelings of grief surrounding these boots into giddiness. Hopefully, these tips can also make you want to buy cowboy boots. Without further ado, let's get into it.

What not to wear with cowboy boots:

Styling is inherently subjective, but if I had to share my thoughts on what tends to look less polished with cowboy boots, I would say double denim, overalls, athleisure, frilly puff-sleeve dresses, fringe outerwear, and overly bold prints. Keep reading to discover more of my opinions and what I recommend pairing with cowboy boots instead.

Are you supposed to wear jeans over cowboy boots?

Yes, you can wear wide-leg or bootcut jeans over ankle-length cowboy boots. An excellent example of this trendy pairing is Sienna Miller, recently spotted in London. She effortlessly pulled together an ensemble featuring a cozy black sweater, chic black bootcut jeans, and striking black cowboy boots adorned with crisp white stitching. This stylish combination showcases how to blend contemporary fashion with classic Western elements. However, to maintain an elegant appearance and avoid a look that feels too thematic or over-the-top Western, it’s essential to ensure your overall outfit remains thoughtful by sticking to a monochromatic look or minimalist pieces.

Avoid: Double Denim

Embrace: Fitted Jeans

If you were to picture stereotypical Western style, you'd likely see layered-on denim separates and cowboy boots. While double denim is trending again when paired with cowboy boots, it can feel a bit too on-theme. Instead of following tropes, try paring back the look by styling fitted jeans with the shoes. It still pays homage to the long history of this fashion aesthetic without making it unapproachable for everyday life.

Avoid: Overalls

Embrace: Miniskirts

Wearing Western-inspired apparel like overalls with cowboy boots can come across as costumey. Instead of adhering to the theme, try pairing your boots with a more timeless staple like a miniskirt. It will ensure you show off your boots and make them feel more elevated.

Avoid: Athleisure

Embrace: Tailored Separates

As much as we all love our cozy athleisure items, they don't exactly mix with cowboy boots that well. Luckily for us, there's a particularly chic alternative the fashion crowd has been pairing with these boots: tailored separates. From blazers to oversize button-downs to trousers, these polished pieces add a level of formality to this otherwise casual boot style.

Avoid: Frilly Puff-Sleeve Dresses

Embrace: Minimalist Dresses

Cowboy boots may be appropriate for roaming the prairies, but you don't have to look like you just came from one. I recommend avoiding the frilly puff-sleeve dresses associated with the cottagecore fashion aesthetic and instead embracing minimalist dresses. Whether you pair these boots with a chunky knit maxi dress, sultry slip dress, or black ribbed number, a more approachable everyday item will make these boots feel timeless.

Avoid: Fringe Outerwear

Embrace: Simple Coats

Don't get me wrong—I love fringe-adorned outerwear and cow-print coats just as much as the next person. But when paired with cowboy boots, the look can feel like a caricature of Western-inspired clothing. Instead of leaning into the whole Wild West thing, pull the reins a bit by opting for a simple longline coat. It will not only ensure your cowboy boots stay the focal point of your look, but it's also a pairing that will work for chillier days.

Avoid: Over-the-Top Prints

Embrace: Neutral Colors

Tons of prints and colors, in general, can become distracting, especially when paired with cowboy boots. If you want your boots to be front and center, avoid wearing any over-the-top items that can take away attention from the main event. One way you can do just that? Opt for simple looks featuring neutral color palettes. It's a foolproof way to ensure these boots look fabulous.

This post was published at an earlier date and has since been updated.