Why I’m NEVER Hiking in a Dress Again

Hiking dresses. So cute, so comfy, so … not functional. I was quick to embrace the concept of the hiking dress when I first got into thru-hiking, but I only made it about 700 miles into the AT before switching to tights.

Initially, I bought into the idea that a hiking dress would mean more airflow, better mobility, and one less thing to keep track of at the laundromat. I also liked the idea of passing my six months on trail wearing something adorable.

So I grabbed a summerweight merino hiking dress off the clearance rack at REI, laced up my trail runners, and set off on that glorious, bug-infested adventure known as the Appalachian Trail.

Several wardrobe malfunctions, infinite thigh chafe, and two mysterious shin rashes later, I decided it was time to throw in the towel. By hiking almost a third of the Appalachian Trail in a dress, I established two key findings:
 

1. Hiking in a dress is indeed possible. Technically.
2. Why TF does anyone ever choose to do so?!

Despite my high hopes, the hiking dress was not all it was cracked up to be. These days I typically opt for shorts or leggings — as the hiking gods intended — and feel much happier and more comfortable that way. Here’s why it didn’t work for me and why I’ll never wear a hiking dress again.

1. The Potential for Wardrobe Malfunctions Is Too Great

Again, but this time in a dress.

Hey, I get it. You haven’t truly lived until you’ve experienced the thrill of accidentally flashing your hoo-ha at an unsuspecting stranger halfway through a Class 3 scramble. And that’s exactly the kind of adrenaline-pumping experience your hiking dress will offer you!

Look, a hiking dress might be a great choice for smooth trails, but I’ve never hiked any long trail that was smooth sailing all the way.

Take the Appalachian Trail: we all know the terrain can get very rugged on the AT, especially up north. The Whites and southern Maine feel pretty much like 150 miles of uninterrupted rock scrambling. Picture gradients so steep they occasionally approach vertical — sometimes involving literal ladders bolted into cliffs, other times necessitating huge steps up and butt-sliding down.

You can see how this could create problems in a hiking dress.

Good thing I switched to pants before reaching this section. I had enough awkward experiences elsewhere on the trail (hello Dragon’s Tooth) to realize that by the time I reached the Whites, my outfit was going to become a major problem.

Besides more technical hiking sections, the dress can also be more of a hindrance than a help in windy conditions. I want my attention focused on my surroundings, not on keeping my skirt from pulling a Marilyn Monroe.

On a similar note, the skirt was about mid-thigh length and I always felt like it was riding up under my hip belt. This led to a lot of anxious ass-patting on my part, just checking to see that everything was still in place. It was a huge annoyance and a pointless waste of energy.

And you can’t even sit normally in a dress! After putting in 20 rock-strewn, root-choked miles, if I see a nice comfy rock alongside the trail all I want to do is flop down on it with my legs akimbo. I don’t want to have to cross my legs all ladylike. This is the Appalachian Trail we’re talking about, not the Princess Diaries!

Some hiking dresses have built-in shorts and you could, of course, just slip your own shorts on underneath for extra security. But that defeats the purpose of having a lighter, airier, more streamlined outfit.

2. Bugs, Poison Ivy, Sharp Things

Hiking in a dress is lovely and cool and grants the wearer access to unlimited cool breezes and plenty of air circulation. It also leaves your legs vulnerable to the myriad flying, biting, stabbing, burning, and poisonous things one finds in nature. This is true for anyone wearing shorts too, but a dress feels even more exposed.

How do I put this delicately? I can’t. OK, I’ll just come out and say it: if you are hiking in a dress, it is likely that mosquitos will fly up your skirt and bite you on the ass at some point during your hike. The hiking dress Establishment doesn’t want me telling you this, but PEOPLE NEED TO KNOW.

Many people thru-hike in shorts/skirts and seem to thrive; I honestly have no idea how they do it. After 300 miles my legs were absolutely shredded from thorns and mosquitoes and accidentally walking into logs and rocks and things. That’s not even counting all the poison ivy, a plant that grows in great abundance on the AT and has no qualms about disrespecting the trail right-of-way.

Finally, the ultimate vulnerability: thigh chafe. Try walking 2000 miles and see if you don’t start chafing in some unexpected places (looking at you, armpits). Rather than lather up with Bodyglide every day for six months, I took an easier road and just put on pants.

3. Less Versatility

On hot days it’s nice to hike in just shorts/tights and a sports bra. Yes, I recognize that this is a direct counterpoint to what I said above. Now is not a good time to examine all my contradictions, leave me alone! The point is, sometimes you have to go with what feels right in the moment, and a dress does not give you the freedom to do so.

Unlike a hiking dress, the shorts-sports bra ensemble also makes a great swimming outfit for when skinny dipping isn’t appropriate.

My trusty hiking leggings have pockets on the thigh, which is clutch because I can keep my phone there for easy access without it interfering with my hip belt. This, in turn, frees up more space in my hip belt pockets for other items.

4. Limited Hiking Dress Options

I suppose in the future, the laws of supply and demand could furnish us hiking dress shoppers with more choices. We’re counting on you, invisible hand of the market! But in the meantime, there aren’t that many purpose-built hiking dresses.

Granted, a few cottage companies offer unique options (Lady Hike, Purple Rain), while many outfitters carry workout dresses that may or may not be tailor-made for hiking.

Arguably I’m overcomplicating things here.  The incomparable Heather Anderson is famous for — OK, scratch that, Heather Anderson is famous for being a world-class athlete, outdoorswoman, and author. But also she wears dresses on trail, most of which she sews herself or picks up in thrift stores. If it’s comfortable and synthetic, it will probably work just fine as a hiking dress; bonus points if it has pockets.

Still, high-end technical hiking dresses made with performance materials remain a rarity in 2024, unlike shorts, tights, and pants.

I’m Sorry, Hiking Dress Lovers! I Tried!

Upon switching to tights I could finally sit with my knees up again AND I was instantly gifted half a gallon of ice cream. Victory!

While I recognize the benefits of hiking dresses in terms of comfort, wardrobe simplicity, and self-expression, the practical limitations are too great for me to justify.

For me, switching to leggings made sense and solved all my problems immediately. A sturdy pair of leggings holds up surprisingly well, even with butt-sliding and rock scrambling. This way I have full range of motion without worrying about awkward wardrobe malfunctions and my legs are protected from the trail and each other. They’re comfortable and do a decent job across a broad range of temperatures.

As I mentioned before, Heather Anderson is all the proof anyone should need that hiking dresses are a perfectly legitimate choice for even the most badass of adventurers.

Hiking dress enthusiasts: don’t hate me! I wanted to be cool like you, but I just couldn’t hang with the poison ivy. How do y’all manage it without nature wrecking your legs? How do you handle scrambly situations? I’m seriously asking.