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What To Wear – Glamping at Paws Up

What To Wear Glamping Edition
Read Carefully

what to wear dude ranch


The question I am most frequently asked about any destination  is “What should I wear?” Every destination has its own packing list, and if you aren’t worried about what to pack, you must be a dude.

Packing properly for a dude ranch is important, there is not likely anyplace to buy what you forgot – and without the proper gear, you’ll miss out on some of the best activities.


What To Wear Glamping



It all starts with the boots – and you build from there. Why boots? You need them to ride, you need them to walk on the dusty rocky roads, and they look super cute. Also, if a horse steps on our foot (yes that can happen) sneakers will not protect your toes. Also, sneakers don’t look cute.


what to wear montana ranch


I pack two pair. These short boots by Frye have been great for both riding and they go with dresses – and shorts. You can buy similar at Frye online. Hot cowboy not included.


what to wear montana.

what to wear montana

Someday when I get a horse-I will name him Champers


My tall Lucchese boots have been all over the world with me. I bought them years ago in Park City, yes they are expensive, because they are worth it. These boots are handmade and honestly, you can tell the difference. I like to try boots on before I buy them, but you can check them out online at Lucchese. They are as comfortable as a pair of slippers and are great for riding and look cute with dresses. Catching the theme here? Functional + cute.


what to wear montana


Kids also need real boots, with a steel toe for so many reasons. First, they will be walking through dirt and poop. Second they are easier to ride in than sneakers. And again, they protect tiny toes in case they get stepped on. Did I mention the poop? The boys’ boots were so filthy every single day, I just rinsed them and set them out in the dry Montana air on our many visits to The Resort at Paws Up.


what to wear kids montana


I found cheap boots for the boys on Zappos. We ended up returning a few before we got the size right, which is the beauty of their quick shipping and free returns. DO NOT forget tall socks to wear under boots. Bring several pairs, I mentioned how filthy they got right?



The sun is intense and hats do more than look good, they also protect your skin. I wore a hat riding but the kids had to wear helmets. Even if that weren’t the rule, I would have made them wear helmets. Keaton’s horse got kicked hard by another horse during the cattle drive. Luckily Keaton is great with horses and his horse is a champ and did not freak out. Never forget that horses are wild animals and you can get thrown, even at a fancy dude ranch. When I rode horses in Dubai I brought my own helmet.


what to wear montana horses

However, hats make for the cutest cowboy photo opps EVER.

what to wear glamping





I thought sunglasses were on the packing list for fishing because it was bright out. Turns out you can accidentally get a hook in the eye, so they’re really for safety. If you’ve ever seen me cast, you’ll know you need to be wearing sunglasses. Also, I really caught this fish, but I remember it being much larger.


what to wear montana

Jeans, Belts and Plaid Shirts


Get your rhinestone cowgirl on. Riding is a dress to impress event. Yes, you can ride in jeans and a t-shirt, but when else will you have an excuse to wear a big old belt buckle? I’ve had many readers ask if their kids can ride in shorts or sweats, yes and no. Shorts on a horse will leave you chapped. Sweats are not that comfortable, and do not make for cute pictures. You will be riding in the woods and scraping up against branches and trees, you want your limbs covered. The belt buckle is just for fun.


what to wear glamping

Swim shorts, rash guards and water shoes


If you plan to spend any time in a fabulous river, say maybe the Blackfoot in Montana, you’re going to want to wear water shoes. The rocks are very slippery and hard to walk on. Shorts are more flattering than a bikini when you’re rafting, kayaking or fly fishing. A rash guard will protect your skin from the sun and keep you cool and comfortable. Same goes for the kids.


what to wear glamping

 Dresses, Mascara and a cute necklace


This is glamping, which is decidedly not camping. There is always a reason to pull on a sundress, a pair of boots and a cute necklace. The first time I went glamping I was surprised to find that so many people dressed for dinner. Of course some arrive dressed casually and no one thinks twice, but the vast majority of guests were dressed in their western best. I bought this necklace when I was at The Resort at Paws Up in Montana. The designer carved a feather out of an elk antler and filled it in with obsidian. My favorite souvenir is always jewelry, then every time I wear it I’m reminded of that fabulous trip. You can see more of her jewelry on her website Chelsea Martini.



What do dudes wear?


Jeans, nice boots and a good looking shirt. This is a great picture of the former marketing director for Paws Up who stood in as the boys’ fake daddy for a recent marketing video. His look is spot on-also a little scruff on the face is totally welcome.




I hope this is helpful. I was not compensated by anyone for pimping their expensive boots, but I wouldn’t say no if they asked. These photos were all shot at Paws Up in Montana, truly the Last Best Place. You can read my review here The Resort at Paws Up.



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