What I Wear When I Walk the Appalachian Trail for a Day
Last Saturday I woke up stupidly early (a rare miracle) with one clear goal: spend a full day hiking a stretch of the Appalachian Trail without turning into a sweaty disaster by lunchtime. The sky was that soft hazy blue, birds were gossiping, and I was determined not to repeat past mistakes — like the time my “cute” white sneakers came home permanently brown.
After years of trial and error (and several humiliating trail photos), I’ve finally figured out a system that feels like me: comfortable enough for serious walking, but still tells a story.
I started with my beloved high-waisted olive green linen trousers — the very same pair I rescued from the Brooklyn Flea. They’re lightweight, breathable, and surprisingly forgiving even after hours of movement. Yes, they wrinkle like crazy, but that’s part of their personality. They make me look like I casually wandered into nature instead of aggressively planning it.
On top, I wore a soft, well-washed white cotton tee that gets better with every laundry cycle. Over that, I brought my hero piece: the mustard-yellow corduroy jacket. I know what you’re thinking — corduroy on a hike? But it worked beautifully. I tied it around my waist during the steep climbs and slipped it on when the breeze picked up on the ridges. The bright color kept lifting my mood every time I looked down.
Footwear was non-negotiable: my trusty broken-in brown leather hiking boots. They’re not the ultra-technical kind influencers love, but they’ve molded perfectly to my feet after two previous Catskills trips. I paired them with thick wool socks (stolen from my brother years ago) for maximum blister protection and zero regrets.
The little details made it feel personal: a vintage silk scarf around my neck (which doubled as a sweat rag and emergency picnic blanket), a small canvas crossbody bag, and my favorite silver hoop earrings that somehow survived the entire adventure.
The trail itself was pure magic — rocky sections that made me curse under my breath, followed by peaceful stretches where the only sounds were wind in the trees and my own dramatic breathing. At one sunny clearing, I sat on a rock, ate a slightly smashed peanut butter sandwich, and felt ridiculously happy to be alive.
The real lesson I learned?
You don’t have to choose between looking decent and being comfortable. The secret is choosing clothes that have already lived a little. They tend to be kinder when you trip over roots or sit on suspicious moss.
By the time I got back to the trailhead, my linen pants had gained new character wrinkles, my boots were proudly muddy, and my corduroy jacket wore a few pine needles like medals. I looked like I had actually done something meaningful with my day — and I loved every bit of it.
Wear your story.
— Chloe Brennan
Williamsburg, Brooklyn
May 2026
