As a Southern gal who grew up near Texas, I love cowboy boots. But for those of us with shorter legs, the traditional mid-calf cowboy boots are so tricky to style.
After living in Nashville for 10 years I definitely got tired of seeing them. And though I’ve been gone for over 10 years now, traditional cowboy boots and my slight aversion to them isn’t out of my system — so I’m easing back into wearing cowboy boots on the regular (but not just any ol’ cowboy boots).
3 Ways To Wear Cowboy Boots & Jeans Now
Last year, I ordered this pair of cute, shorter cowboy boots by Matisse and dabbled with them a few times, but I never wore them a ton until recently. After a little time apart, these boots were just what I needed. They felt new, inspiring, and like the perfect way to mix it up from my everyday sneakers.
And because they’re so heavy in my rotation, here are three ways I’m styling cowboy boots with jeans right now…
1| Half-Tucked With Cropped Slim, Straight-Leg Jeans (MOTHER The Tomcat)
This was the jeans + boots combo that inspired this article. I did a whole review of these jeans here if you’re interested, but it turns out the Mother Tomcats work great with shorter cowboy boots! I do a kind of half-tuck of them (they are a cropped fit, slim leg) and it works so well.
I could never pull off the tucking-jeans-into-regular-cowboy-boots look. Taller folx can rock that, but on this shortie, it just did me no justice and made me feel squatty. This combination, however, I love! It’s something new and different and is making me have fun with my outfits right now.
Blazer (8) | Jeans (29) | Boots | Bag
I do think it works most seamlessly on me when the jeans and boots are of similar value (ie. both lighter or both darker.) And I prefer the look with my tee tucked, too. And don’t worry too much about the jean tuck being perfect here. I just pop one side of the jeans in the boot and leave the other side out over it.
More to come on this rag & bone Slade blazer, too…but I’ve wanted to try it forever and it’s SO good. Just size up (I needed to go with an 8) and size up one size on the Mother jeans, too. Wearing a 29.
2| With Full Length, Wide-Leg Jeans (Moussy Vintage Odessa)
This next outfit is just an easy combo here with no tucking AND is quite leg-lengthening, too. These Moussy jeans are one of my absolute favorites because the brand really nails that vintage wash.
I love that these are wide leg (but not too wide) so they lay nicely over the cowboy boots. Plus, they have the perfect distressing I love as well. They feel especially cool paired with my new fav quilted BlankNYC jacket. I bought it locally and they only had a M, but I probably could have stuck with my typical S. It is SO soft and I grab it all the time.
Jacket (m) | Tee | Jeans (29) | Boots | Bag | Jewelry
3| With Ankle Length, Straight-Leg Distressed Jeans: (AGOLDE 90s Loose Fit)
You’ve seen these AGOLDE jeans** a ton (like in my full review here) and I’m still loving them. They are also a wider straight-leg and I’ve cropped this particular pair to just above my ankle.
That’s what I love about having a perfectly cropped pair of jeans — they’re so good to wear with my high tops and higher shaft boots. They show just the right amount of the upper of the shoe in this length.
**Indicates meets our requirements for sustainability.
Sweatshirt (m) | Jeans (28) | Boots | Similar Bag
I like this look with my Anine Bing Paris sweatshirt in even more of a tucked situation (shooting in the wild is always precarious, friends haha) or with a bit of a cropped top or jacket. This combo would also be cute with a longer jacket…I love playing with the short/long combo when putting looks together.
Shop More Cute, Short Cowboy Boots
I LOVE my pair of cowboy boots by Matisse and they’re very comfy, but I recently ran across some other adorable pairs, too. So I’ve included a few of my favorite shorter cowboy boots to kick us off here (heh.) I’ve ordered the light Dolce Vita boots to try out next. I also have the Free People pair in a snake print from a few years ago, but am loving some of their solid shades now.
Thank you, fun cowboy boots for getting me out of my fashion rut this year and for being comfy yet cool.
What shoes are inspiring new looks for you right now, friends? These transition times between seasons always seem so tough to figure out when it comes to getting dressed, but it’s nice to have one new piece that helps inspire the ol’ brain. Let me know what you’re loving!
Would love for you to say hi over on my Instagram @laurajansenstyle where there are mostly odes to snacks, OOTDs, and everyday mom life stuff in Portland, Oregon. xoxo
Lovely photos per usual by my pal Posy Quarterman.