My Style Guide on How to Dress in Montana: Fall Edition

What I’m wearing for cabin weekends, days in Bozeman, and the colder months ahead.

Fall has always been my favorite season to get dressed in Montana. I love the first few weeks when the mornings are cold enough for a sweater but the afternoons still feel like summer. It’s the time of year when I start pulling out my jackets, wearing boots again, and finding new ways to style the pieces I’ve had for years.

September and October can be surprisingly warm here, so I’m not quite ready to put away my summer wardrobe. I’ll wear shorts with a blazer or a barn jacket, a dress with boots, or a button-down tucked into jeans with a sweater over my shoulders. The extra layer usually makes the outfit better anyway.

This year, I’m leaning into barn jackets, waxed Barbour jackets, dark leather boat shoes, loafers, suede, and cowboy boots. I’ve also been collecting a lot of inspiration around vintage Ralph Lauren, beautiful tailoring, fringe, and the way classic pieces can be worn a little more casually. I love a good coat with old denim, a feminine blouse with a rugged jacket, or a pair of cowboy boots with something that otherwise has nothing western about it.

As a sixth-generation Montanan, I’ve never felt that there is one way to dress here. The clothes I wear for a day fishing are obviously different from what I wear to dinner, but there is usually some overlap. A sweater comes along for both. The same pair of jeans might be worn three different ways over a weekend. A jacket that looks beautiful in town should also be something I’m happy to wear outside.

Here’s what I’m reaching for this fall, and how I’m putting it all together.

For a Weekend at the Cabin

I can spend an entire weekend at the cabin in varying versions of a cashmere set. I love the Quince cashmere sets, and my Negative Underwear Whipped pajamas are another favorite. They’re the pieces I reach for first thing in the morning and usually end up wearing well into the afternoon.

I’ll throw on a pair of sherpa clogs or sandals, make coffee, and settle in with a book or whatever we have planned for the day. If we’re heading outside, I’ll add a barn jacket or a big sweater. I love having a few sets packed so I can change into something fresh without feeling like I’ve actually gotten dressed. It’s probably my favorite way to spend a slow weekend.

For an Afternoon on the Trails

Horseback riding is where I feel most at home in my old denim. I’ll wear my favorite pair of jeans, worn-in Luccheses, and a flannel or denim button-down. A baseball cap is a must. I rarely ride in a cowboy hat.

I always bring a jacket to slip on afterward, especially if we’re staying for a drink or dinner. A suede jacket, barn jacket, or something with a little fringe can take the same outfit into the evening without needing to change. I love that the pieces I wear riding are often the ones I want to wear the rest of the day, too.

For a Work Day Downtown Bozeman

For work, I lean a little preppy meets western. One of my favorite Ralph Lauren button-downs, a great pair of denim or tailored trousers, and a fringe jacket is a combination I come back to constantly.

I’ll usually finish it with my boat shoes or loafers, a leather belt, and a good bag. I love the contrast of a crisp shirt with something a little more rugged, and I think it feels especially right for downtown Bozeman. It’s polished enough for meetings but still comfortable for a day running between the office, coffee, and Main Street.

For a Morning Hike and Coffee Run

You’ll usually find me in one of my favorite Alo sets, my Salomons, Ray-Bans, and a Halfdays fleece. It’s an easy uniform for a morning hike followed by coffee, and I love having pieces that I can wear for the rest of the morning without changing.

I’ll usually bring a baseball cap and a tote, and if it’s especially cold, I’ll add another layer. I tend to keep my athletic wardrobe pretty simple, so a good fleece or jacket is what makes the outfit feel a little more complete.

For an Afternoon Fishing

For fishing, I love my KÜHL pants and a Duckworth pullover if it’s cold. If the sun is coming out, I’ll wear a flannel with a bandana instead. My straw hat is a must.

I’m always dressing for the weather and the actual day on the river, but I love the pieces that come along with fishing. A good flannel, a worn hat, and a pullover that has been on countless trips are some of the things I reach for most often. I’ll usually bring a jacket for afterward, especially if we’re heading somewhere for a drink or dinner.

For an Evening Around the Campfire

You’ll find me in my favorite worn jeans, boots, and a barn or waxed jacket. A baseball cap is optional, although I’m usually wearing one. I love a big sweater underneath if it’s cold, and I’m always happy to bring out a jacket that I don’t have to worry about getting a little smoky.

If I’m somewhere like Montage and want to look a little more put together, I might swap the baseball cap for one of my Montana Territory cowboy hats. It’s an easy way to dress up the same outfit without changing much else.

For Pre-Dinner Drinks

For pre-dinner drinks, I love a long suede skirt or leather pants with one of my favorite cashmere cardigans. I’ll throw a fringe jacket over my shoulders and usually add a little turquoise, whether that’s a pair of earrings or a cuff.

I’m particularly drawn to chocolate brown, cream, and burgundy this season, and I love mixing those richer colors with suede and leather. A great pair of boots and a beautiful bag are usually all I need to finish the outfit. It feels dressed up, but still very much like something I would wear in Montana.

For Dinner in Big Sky

This one depends on where I’m going, but I love a long-sleeve knit midi dress with a barn jacket over my shoulders. The jacket balances out the dress and keeps it from feeling too formal, which is exactly how I like to dress for dinner here.

A great clutch and boots does it for me. I might add a pair of earrings or a cuff, but I usually keep everything else pretty simple. I love an outfit that feels considered without needing too many pieces, especially when the coat or jacket is just as much a part of the look as the dress underneath.

A New Season, In Good Company

A few things setting the tone for Fall…

I always find myself collecting inspiration as the seasons change. Sometimes it’s a room I can’t stop thinking about, a collection that makes me reconsider what’s already in my closet, or a photograph that captures exactly how I want the next few months to feel. I love seeing how those ideas find their way into what I wear, how I entertain, and the places I choose to spend my time.

My Pinterest is where I keep all of it, and I’ve put together my full fall curation on ShopMy, including the pieces I’m wearing now, the ones I’m considering, and a few things I think are worth knowing about.

Explore my Pinterest · Shop my fall curation

A Note on Getting Dressed

The best part of a Montana wardrobe is that it has to work for the life you actually live. A great pair of boots should see more than the inside of a closet, and a jacket should be just as useful on a trail as it is over your shoulders at dinner. I’m always drawn to pieces that get better with wear and can move between the different parts of my day.

This is the wardrobe I’m returning to this fall: familiar favorites, a few new additions, and plenty of reasons to get outside. I hope it gives you a little inspiration for your own season ahead. xx