After searching for outfit inspiration for my Aspen trip, I was reminded that I still haven’t shared my outfits that I worn in Montana and Jackson Hole that have a similar vibe. You could easily wear these outfits to Aspen in the Winter also and just add some faux fur coats/warm weather accessories, or for any other trip where you’re looking for a Western Chic vibe. Keep reading to shop my Montana and Jackson Hole Outfits and bookmark this post for your next trip!
#1 Denim on Denim
Denim on denim is a classic go-to for a Western-inspired look, and this outfit is perfect for Montana or Jackson Hole. The high-waisted jeans paired with a tucked-in chambray shirt create a flattering, effortless silhouette, while the black cowboy hat and belt add just the right amount of contrast.
A pair of worn-in boots complete the look, making it ideal for everything from horseback riding to strolling through town. Whether you’re headed to a ranch or just channeling those rustic vibes, this outfit is an easy, stylish choice for embracing the Western aesthetic.
#2 Casual Contrast
The contrast of the knit sweater with the structured shearling-lined jacket gives that perfect mix of rugged and refined, while the light-wash denim keeps things casual and easy to wear. A black cowboy hat and boots tie it all together, adding just the right amount of Western flair.
Whether you’re exploring Big Sky or just enjoying a crisp mountain morning, this look is stylish, functional, and perfect for layering up in true cowboy-chic fashion.
#3 River Wrangler Chic
Easy, breezy, and perfectly Western—this look is made for warm days in Montana or Jackson Hole. A simple $11 vest tank and denim cutoffs keep it casual, while the black cowboy hat and boots add a classic ranch-ready touch. Whether you’re by the river or out exploring, this outfit is effortless and timeless.
#4 Western Romance
This outfit is giving Western romance in all the best ways. The flowy white dress brings a soft, feminine touch, while the denim vest and cowboy boots add just the right amount of rustic charm. A wide-brim hat ties it all together, making it perfect for twirling by the river or strolling through town. Whether you’re headed to a summer rodeo or just soaking up the Montana scenery, this look is effortlessly chic with a hint of romance.
#5 Open Back Canadian Tuxedo
Denim on denim, but make it Western. This vest and shorts combo is effortless, I love the open back detail. The tall cream boots add the perfect contrast and of course I topped it off with a classic cowboy hat. It’s an easy, laid-back look for western chic adventures.
#6 Wild Wild Western
Western meets wild with this chic look. I love that this leopard-print dress was unexpected and adds a bold touch, while the camel coat and black cowboy hat keep it classic. Paired with tall boots and a statement belt, it’s the perfect outfit for a night under the open sky—glass of wine optional but recommended.
#7 Little Slip Dress
Effortlessly Western and a little bit glam, this look is perfect for a Montana or Jackson Hole evening. Both my friend and I had the same vibe going on here. A sleek black slip dress with a high slit keeps things elegant, while the statement belt and white cowboy hat add that signature Western edge. Paired with tall boots, it’s the perfect mix of classic and modern cowgirl.
#7 Off Shoulder + Effortless
Another note-worthy dress moment from this trip, this look is all about effortless ranch elegance. A flowy off-the-shoulder dress paired with classic cowboy boots gives off a dreamy Western vibe, while the wide-brim hat adds the perfect finishing touch. Whether you’re sipping wine at sunset or twirling through the fields, this outfit is made for golden hour moments.
#8 Romp Around Town
This look is giving Western cool girl energy. A sleek black romper cinched with a belt keeps it chic, while tall cowboy boots and a classic hat add the perfect rodeo-ready touch. Whether you’re shopping in Jackson Hole or stopping by the Million Dollar Cowboy Bar, this outfit is made for turning heads.
Also wanted to call out this cute denim dress that I loved for our day at the hat shop. Would be such a cute look for rodeo.
And close up details of the hat I had made! A must do when you visit.
And another romper I have to call out – this green number was so cute and comfy.
#9 Elevated Cowgirl
Western with a touch of city chic—this outfit is the perfect balance of casual and elevated. A silky black top paired with a denim midi skirt keeps things classic, while strappy heels add a modern twist. The black cowboy hat ties it all together, making it an effortless choice for a night out.
#10 Timeless Western
Timeless Western with a polished touch—this outfit blends classic ranch vibes with effortless sophistication. The rich brown blazer and camel-toned top pair perfectly with wide-leg denim, while the cowboy hat and boots keep it true to its roots. Perfect for crisp Montana mornings or a stylish day in Jackson Hole.
#10 Cowgirl Chic
Cowgirl meets city chic! A tailored blazer elevates classic denim cutoffs, while white cowboy boots keep it Western. Perfect for strolling through Jackson Hole in style.
#11 Western Glam
Western glam at its finest! A sleek faux leather skirt meets bold black cowboy boots for the perfect mix of edgy and elegant. Ideal for a night out in Jackson Hole.
#12 Crisp Cowgirl
A crisp knit top, light-wash denim, and a cowboy hat make this the perfect laid-back yet stylish look for a day in the Tetons.
#13 Effortlessly Cool
One of my favorite looks – I took this quick photo while packing so I had it to refer to once on the trip! An oversized white button-up paired with distressed denim Bermuda shorts creates the perfect relaxed vibe, while cream cowboy boots add a Western touch. Simple, chic, and ready for anything.
How to Add a Western Touch to Any Look
Adding a Western touch to any outfit is all about the details! A statement cowboy hat instantly elevates your look, whether you’re keeping it casual or going full rodeo-ready.
Swap out your everyday belt for one with a Western buckle, turquoise accents, or leather details to bring a subtle nod to the trend.
And of course, no Western-inspired outfit is complete without the perfect pair of cowboy boots—whether you go for a classic neutral or a bold pop of color, they’ll pull your whole look together effortlessly.
Looking for more travel outfit inspiration? Check out What to Pack & Wear for Aspen
