Fall is hands-down the best season to hike. The air is cooler, the views are better, and you can finally wear layers without melting by mile two.
But the styling part? Kind of a nightmare.
Too light and you’re freezing.
Too bulky and you look like you dressed in the dark.
The goal is layers that work *and* look like you still have your life together.
So we did the work for you.
These 15 outfit ideas hit that sweet spot between cozy and functional—stuff you can actually move in, but that still makes you feel like you’re the best-dressed person at the overlook (because you are).
Fleece, flannel, real shoes.
👉 Keep scrolling for the fall hiking looks that’ll carry you from trailhead to cider stop—with links to shop everything, obviously.
1. Beanie + Flannel Jacket + Black Jeans
This is basically the pumpkin spice latte of fall hiking fits—and we say that with love. Cozy, classic, and totally dog-walk friendly (yes, even if your trail is more gravel path than peak summit).
2. Long-Sleeve Tee + Dark Jeans + Shirt Tied Around Waist
This is your “I totally didn’t try but still look like a fall catalog model” outfit. It’s equal parts cozy and cool—perfect for golden hour hikes or post-s’mores fire pit vibes.
3. Crop Tank + Windbreaker Pants
When you want to serve sporty spice energy *and* be rustle-free in the forest—this is your go-to. Add a light jacket if the air’s crisp, or just strut that trail like it’s a runway.
4. Fitted Long Sleeve + Cinched Cargo Pants
This look says “I’m here to summit a peak and maybe flirt with a forest ranger.” The fitted top keeps you sleek, and the cinched cargos give serious mountain babe energy.
5. Crop Tank + Linen Button-Down + Rust Hikers
Peak fall trail vibes: breathable up top, cozy-utility on bottom. The linen shirt is your lightweight layering MVP, and those rust cargos? They basically scream *pumpkin spice but make it rugged.*
6. Graphic Tee + Utility Overalls + Flannel Waist Tie
This outfit is giving “cool camp counselor meets REI chic.” The olive overalls say “I’m here to hike,” the flannel says “but I also brought cider and a good playlist.” Bonus points for those classic high-top kicks. 🍂🛤️
7. Hoodie + Puffer Vest + Leggings
If “fall cozy core” was a sport, this ‘fit would take gold. The hoodie keeps you warm, the vest adds just enough puff, and leggings = ultimate trail stretchiness. Bonus: that beanie gives 🍁 PSL energy in the best way.
8. Tank Top + Hiking Skirt + Flannel Around the Waist
For those in-between fall days when the sun’s still flirting but the breeze says “don’t trust me.” A hiking skirt gives breezy freedom, the flannel is your just-in-case hero, and the tank keeps things chill. Add a baseball cap and boom—main character moment.
9. Long-Sleeve Tee + Statement Cargo Pants
Yes, you can absolutely serve a ~lewk~ while hiking. A fitted long sleeve adds warmth without the bulk, and the cargo pants with fun pockets or patchwork details say, “I know the trail and the trends.” Add a pop-color backpack and you’re a walking REI ad in the best way.
10. Rain Jacket + Black Leggings
This is your power move for those moody fall days that *might* sprinkle or just look dramatic. A structured rain shell in army green feels chic and utilitarian, while black leggings keep it classic. Bonus points if your hiking boots match your energy (and your socks).
11. Long-Sleeved Top + Red Cargo Pants
This is your main-character moment. A fitted neutral top balances out the boldness of red cargos—perfect for crisp air and golden hour selfies. Toss on lace-up boots and you’re basically starring in a moody REI commercial (but, like, hot).
12. Colorblock Windbreaker + Black Leggings
Moody skies? Light drizzle? This colorblock cutie’s got you covered. It’s giving practical without sacrificing the vibe—especially when paired with classic black leggings and waterproof boots. Trail fashion forecast: 100% cute with a chance of compliments. ☁️🍂
13. Puffer Vest + Sweatshirt + Light Wash Jeans
If “crisp air and camp coffee” were an outfit, it would be this one. A cozy neutral vest over your go-to sweatshirt, paired with laid-back denim and sturdy hikers = peak fall fashion energy 🍁☕
14. Hoodie + Denim Jacket + Straight-Leg Jeans
This coastal trail slay is giving *main character in a fall rom-com*. A hoodie layered under a denim jacket = peak cozy cool, especially when paired with vintage-fit jeans and bold boots. 🍂💘
15. Cargo Pants + Crop Tank + Hiking Boots
If Lara Croft went on a chill fall hike with a Stanley in hand, this would be the look. Functional, flirty, and absolutely trail queen-approved. Bonus points if you’ve got gear clipped to your belt loops. 🏞️💪
