I bought this pair of short cowboy boots from Reformation last month (in taupe, obvi), and yeehaw — they’re good. Up until fairly recently, Philly was still pretty warm, so I’d contented myself by wearing them with denim cutoffs and little dresses, which, frankly, are still my favorite ways to style cowboy boots.

But once the weather started to cool…jeans. I needed jeans.

I started popping these cowboy boots on with all sorts of cropped denim, and dang hooey (is that a cowboy term??), they just looked funny. I’m still in the process of figuring out exactly which freaking pairs of jeans actually work with cowboy boots (stay tuned — a video is coming out eventually), but spoiler: Bootcut jeans are a total win.

What Are The Best Jeans For Cowboy Boots? Bootcut Has My Vote

sweater (S) | jeans (27, more sizes here) | boots

While I love the idea of tucking jeans inside my cowboy boots, in practice, it doesn’t look great. Shorter cowboy boots (like the Reformation pair I’m wearing) makes the tuck easier, but I still wanted a sleeker line.

The whole boot is pretty sleek — the pointed toe, the tall-ish (but walkable) heel — but with a decidedly casual vibe. Bootcut jeans, in this case, are the perfect pairing. (This shouldn’t be surprising; bootcut jeans were basically made for cowboy boots.)

sweater (S) | jacket (XS) | jeans (27, more sizes here) | boots | similar bag | similar sunglasses

In addition to pairing these Western boots with some chic bootcut jeans, I finally picked up one of those Free People Pippa Packable Puffer Jackets. It’s bizarrely lightweight, the colors are so fun, and it can really go with any outfit this winter. I can see why everyone gets so swoony about this puffer.

sweater (S) | jacket (XS) | jeans (27, more sizes here) | boots | similar bag

I’d be remiss if I didn’t also mention this 100% cotton Quince sweater. It reminds me of a similar Jenni Kayne sweater, which, frankly, I haven’t yet tried because this particular sweater is so freaking good aaaaaand…under $40.

sweater (S) | jeans (27, more sizes here) | boots

Shop More Bootcut Jeans

Since my exact bootcut jeans are running low on sizes, I rounded up some similar pairs. Additionally, there are a few additional jeans in the widget below that I also own (and would recommend), so I included fit notes for those as well.

How are you wearing boots and jeans? Let me know!

xo,

S

This one is for the Pin lovers…