5 Outfits I Wore in Montana That Earned Me Tons of Compliments


(Image credit: @gracejoshua13)

If there is one thing I love it's all things Western. Cowboy boots, bourbon, horses, you name it—I'm into it. So when Lone Mountain Ranch reached out to me and wanted to have me come check out its property in Big Sky, I couldn't say yes fast enough. Not only was I going to get to live out my Yellowstone fantasy, but I was also going to get to plan a few Western-style outfits to wear in Montana. Music to my ears.

Lone Mountain Ranch took everything into its own hands, planning an entire itinerary for me and several other women visiting the ranch for the annual "Cowgirl Up" week, which is designed for women to come alone or bring friends for a week filled with horseback riding, wine tasting, archery, axe throwing, fly fishing and of course visiting the national park. With my itinerary already done for me, all I really needed to worry about was what I would wear. After digging through tons of inspo from my favorite coastal cowgirl influencers and tons of old Wrangler and Ralph Lauren ads, I packed my bags and headed to the West.

Once I got there, I immediately fell in love. It was my first time in Montana, and I was expecting to think it was beautiful, but I have to admit, I fell hard. I'll definitely be back soon. Staying on the ranch was like a dream, I met so many women who have been coming to this exact week on the property for years with other women they met on their first trip. There were best-friend duos, mother-daughter duos, and other solo travelers like me, many of whom I would consider friends after the week we had.

While I was there five of my outfits stood out among the rest. From the looks I wore while horseback riding to my dinner outfits, keep scrolling to see which five earned me tons of compliments on my trip. 


(Image credit: @gracejoshua13)

When I first saw this brown-and-white matching set, I knew I wanted to save it for something special, and once I learned I was heading to Montana it was the first outfit that came to mind. It has that pretty coastal cowgirl vibe. I wore this to have dinner and drinks on the property and got so many compliments from the other women on the trip. This was probably the dressiest I got while on the trip and maybe even my favorite. I love it when I get to embrace my inner southern belle if you will with romantic sets like this one.


(Image credit: @gracejoshua13)

I was really living my best Yellowstone fantasy with this look. Doesn't really get more Western than a cowboy hat and fringe. When looking for a good fringe jacket, I found that Boot Barn had so many great options, but I absolutely fell in love with this brown Idyllwind fringe jacket. I paired it with this cozy cashmere sweater from COS which I plan to wear all season long, my Banana Republic jeans, and my most-worn cowboy boots from Austin-based brand Alvies. The cowboy hat was an obvious yes, I think I wore it every day I was in Montana. 


(Image credit: @gracejoshua13)

On the list of things I love to do, drinking wine in a cowboy hat is very close to the top. During my stay at the ranch, the hotel partnered with wineries from Napa to do a dinner where each course was paired with a specific wine, which was personally one of my highlights of the trip. The dinner was six courses, so I needed to pick a dress that was comfortable and stretchy but still on the pretty side. Leaning into my Beth Dutton cosplay I opted for this long-sleeved knit dress from Aritizia was the first thing that came to mind, I need it in every color. I dressed it up with gold jewelry and added my cowboy hat (of course). This look was definitely a fan favorite. 


(Image credit: @gracejoshua13)

For one of my riding looks I decided to swap my cowboy hat for a trucker hat. If you know me, you know that I have quite the collection of trucker hats and can often be found running around New York wearing one paired with a workout set, so this is sort of my Western take on that. This Caviar Cowboy hat felt fitting for obvious reasons but also because it's how I would describe my fall aesthetic. Caviar or cashmere cowboy you get the vibe—it just means an elevated Western way of dressing. Think stylish New Yorker with a second home in Montana. Since I was horseback riding, I needed to wear something easy to move in and that I could fit in my boots, so I decided to give my jeans a break and go for my favorite leggings of all time: ALO leggings. This Helsa denim jacket was the perfect touch and added a little extra oomph to this look. 


(Image credit: @gracejoshua13)

I wore this outfit to meet my horse for the week (pictured above) and the rest of the women joining me for the week on the ranch. It was a little chillier, so my 7 for All Mankind jacket was the perfect extra layer. Coming off of a long day of travel, I wanted to look dressed up, but honestly, I didn't have a lot of energy in me to get too dressy. My Banana Republic jeans and Skims long-sleeve shirt came to the rescue. I just added this Western chain belt and hat to pull everything together.

Assistant Editor

Originally from Chicago, Illinois, Grace has always been a lover of all things fashion and beauty. Upon receiving her first degree in visual communications from FIDM in Los Angeles, she moved to New York City and continued her education at LIM College, majoring in fashion media with a minor in society and culture. Grace has worked for PhotoBook magazine, Insider, and Harper's Bazaar. As a writer, Grace has had pieces published covering topics including racial justice, fashion, politics, and current events. During her free time, she loves wine tasting, creating content for her social media, spending time with friends, traveling to new places, and Pilates, and has a love for reality television, especially The Real Housewives. Grace is the person in your friend group everyone goes to for recommendations for the best place to grab drinks in NYC on a Friday night or the best hotels and restaurants to try when traveling to a new city. While fashion is her main love, she loves all things wellness and lifestyle as well. Her ideal sunday is brunching with friends then walking around furniture shopping and listening to a podcast. As the assistant shopping editor at Who What Wear, Grace loves finding the best buys out there for the WWW readers.