Jolly Gear Triple Crown Button Down Sundress

As a petite hiker who has long been in search of a trail dress that was as functional as it was stylish, the Jolly Gear Triple Crown Button Down Sun Dress provides all of the benefits of the Jolly Gear Button Down Long Sleeve, but with additional features that make it a functional trail dress.

Many other trail dresses on the market are often made of fabric, like a cotton blend, that makes me hesitate to use them in most three-season conditions. Others which are made of synthetic blends often lack sleeves or pockets. As someone who wanted a dress that was just as useful in town as it was on trail, I found that this sundress met my needs well.

I originally wore this sundress on my Collegiate Loop thru-hike in July of 2025, where I was hiking in temperatures between 32 and 80 degrees Fahrenheit. I wore the dress in windy and rainy conditions, including underneath an insulating layer and a rain jacket in a storm that brought several inches of rain to the Collegiates in 48 hours. I’ve also worn this dress on two overnights on the Arizona Trail, in conditions that were within the same temperature range but significantly drier. When I backpack, I only bring one set of clothes to hike in. My other clothing is either insulating layers or rain gear, and during my Collegiate Loop hike I went spent six days in between my single resupply on the trail.

This dress was very comfortable to hike in. I didn’t experience any kind of rubbing or chafing when I wore it at all. I also love all of the features that show the dress was clearly designed with thruhikers in mind. The two zippered pockets are located on the chest, so you don’t have to worry about taking your pack off to access them, and they are big enough to hold an iPhone17. The dress is long sleeved, with thumbholes, and hooded, with a vent that you can pull your braided pony tail through. The hood also has a cinch cord with locks so you can adjust it to your needs. The button down style means that it can be opened at the chest for ventilation, and the drawstring waist allows the dress to be adjusted so it can fit your body the way you want. It also includes a snap on the skirt so it can be converted into a trail romper. The dress is made of 86% polyester and 14% Spandex, and I found that it dried relatively quickly.

I loved all of the features that this dress had that isn’t often found in women’s trail gear, so I didn’t have to compromise on functionality at all. I made use the snap to turn the dress into a romper on windy days and found that it stayed in place. I also got many compliments from people of all genders that I ran into on the trail, who thought it was so unique and special that I hiked in a dress. So if nothing else, this piece is a conversation starter.

This piece functioned well enough that I want to use it on all of my hikes going forward. However, there were a few things that limited the functionality of the dress. After 48 hours of rain on the Collegiate Loop, even though the dress was dry and the temperatures were above freezing when I hiked out, I didn’t feel comfortable wearing it directly against my skin, even underneath an insulating layer. The fabric felt cold and clammy. Although I could wear my legging underneath it easily, I opted to hike out with just my baselayers into down that day as opposed to wearing the dress over them because the cut of the sleeves made it difficult to fit a baselayer longsleeve top underneath without being too tight.

In addition, as a small hiker (5’3″, 105 lbs) I had to order the smallest size in the dress, an XS, and even then I have to hike with the waistband cinched all the way down. This means that the drawstring cord is at its full length and easily caught in my hipbelt, and I will likely cut it down myself before the next trip.

And finally, even though Jolly Gear offers fun and bright patterns for many of their other products, the only colors this dress is currently available in are a white pattern with purple images across the top, and a sage color. While I can’t say why these colors were chosen in particular, and I never felt overheated in the dress, the light color did give me pause as someone who menstruates. I didn’t feel confident enough to wear over the underwear I chose to wear on trail, even as someone with a regular and predicable cycle. Instead, I opted to wear a pair of shorts underneath the dress as well. I also found that the fabric picked up dirt easily, which may not be as noticeable for the button down shirts–but if you are wearing a dress and opting to sit directly in the dirt as opposed to on a sit pad, it was certainly more noticeable. Still, the dress was very fun to wear and I found most of the features extremely useful. I haven’t worn any other trail dresses besides this one, because other products currently on the market don’t seem to come close to its functionality at all–the long sleeves alone make this dress much more practical than most other trail dresses I have seen, which have short or no sleeves, meaning that they offer very little sun protection.