This is What Autumn Feels Like: From Trailhead to Town

September 14 2025, 9 min reading time

Autumn adventures deserve outfits that work hard and feel good. From scenic trails to small-town strolls, here’s how I styled my fall road trip to Glacier National Park: colorful, comfortable, and completely me.

There’s a certain kind of magic that happens when you’re on a road trip: music buzzing through the speakers, coffee in the cupholder, 14 hours of driving down and the mountains finally come into view. That moment when the views shift from desert lands to mountain trees, the air feels just a bit crisper, and you roll down the window just to breathe it in.

This fall, my husband and I celebrated our anniversary with a trip to Glacier National Park, and let me tell you, autumn in the mountains fills up my soul! Crisp air. Orange and yellow leaves are starting to appear between the pines. Golden hour peeking through the evergreens. Everything feels quieter but richer, like the world is turning the volume down just enough so you can finally hear yourself again.

While there’s serenity in nature, there’s often chaos when it comes to packing for roadtrips, mountain towns, hiking, and anniversary celebrations. This year, I finally nailed the best combination of cute on a hike and cuter in the town outfits and I’m here to share the secret sauce. 

So, here’s how I styled from trailhead to town, and how you can too.

Road Trip Style: Comfy, Cute, and Camera-Ready

Let’s be real: no one wants to sit in a car for 14 hours in stiff denim or tight dresses. But that doesn’t mean you have to settle for feeling frumpy. Personally, I wanted to feel stylish, photogenic, and like myself - without sacrificing comfort.

My go-to formula for a fall road trip outfit?

• Soft fabrics with a little structure (think cotton cargos, stretch overalls, or ribbed knit sets)

• Matching sets in neutral or earthy tones (cream, moss, sand… they hide wrinkles and help calm the “are we there yet?!?” anxieties)

• A light layer you can pull on or off without messing up your hair

• Minimal makeup + comfy sneakers = road trip beauty done right

Extra tip: since you’ve got so much time sitting in the car, why not throw on an eye or face sheet-mask?? It helps to refresh the skin, keep you feeling alert, and gives you more time to care for yourself.  

Style Psychology Tip: Matching sets and monochromatic looks signal harmony and intention. They visually “hold you together” even when you feel road-weary. Earth tones, especially, bring a sense of groundedness and ease.

The goal? Comfort that doesn’t look like pajamas. Bonus points if the outfit can transition into a quick photo op when you pull over for scenic stops (or roadside pumpkin patches!).

Trail-Ready Style that Works Hard (and Looks Good Doing It)

Fall hikes are all about layers. Temperatures fluctuate wildly, especially in high-altitude places like Glacier where it snows any time of year and gets to 100 degrees in the same day, so your outfits need to balance function, temperature control, and flair.

Here’s what worked for me (and why):

• Colorful activewear: Not only do brights pop in photos (yes, even against all that autumn foliage), they’re also a safety win if you get separated or want to be more visible on less-traveled trails.

• Breathable layers: My lightweight zip-up jacket over a fitted tank gave me a range of motion and options, plus thumb holes in the sleeves? Always a yes.

• Bike shorts or high-waisted athletic shorts with pockets: Because phones, snacks, and chapstick should never live in your bra and can be a hassle to dig out of backpacks. 

Style Tip: Athletic clothes with color blocking or contrast stitching create curves and movement in photos. Lavender, teal, and magenta are especially striking next to rock and forest backdrops.

Style Psychology Insight: Wearing bright or saturated colors in nature can boost your mood. Warm tones like coral, fuchsia, or turmeric stimulate energy, while cooler greens and blues foster calm and clarity.

Small Town Evenings: Remix Your Hiking Gear

Once you’re done chasing waterfalls and fighting for the last Huckleberry ice cream cone, it’s time to head into town. But don’t worry, you don’t need to change your entire outfit.

Here’s how I turned my trail gear into dinner-date-ready without needing a hotel room:

• Swap your shorts for jean cutoffs, flared leggings, or slouchy slacks

• Throw a jean jacket or cozy cardigan over your workout top

• Add a swipe of lipstick, a touch of mascara, and maybe a bold earring and suddenly you’re golden

One of my most vivid memories from this trip was sitting on our hotel balcony with a glass of wine in hand, admiring the way the evening sun danced through the alpine leaves. I was still wearing the same tank top I hiked in, but I felt polished and put-together with my wide-leg pants and vintage scarf thrown around my shoulders. All it took was a few intentional swaps.

But the outfit that captured my heart and my confidence? The one I wore for our anniversary dinner: a silvery-blue silky, strappy little number with bold flower print, a simple gold chain, and bold flower earrings paired with my platform sandals (because I did not want to turn my ankle on those mountain town sidewalks) and a leather jacket. It was simple to throw on, I felt like a million bucks, and everything felt so comfortable and sexy to wear! Was I overdressed for where we went? 1000%. Did I care? Not at all. 

Fernweh Flair Note: This is what we mean by wearing your story: letting your clothes follow you into every version of your day, instead of forcing yourself to become someone new just to fit a setting.

Real Talk Reminder: Be odor-conscious! Yes, women sweat, especially on hikes. And while you can remix your trail outfit into something dinner-ready, if it was a steep climb or an unusually warm day, go ahead and switch out your top (and/or other pieces) and freshen up. A quick deodorant re-up or a swipe of body wipe can go a long way, for your comfort and your fellow travelers’ noses. No shame in the sweat game, just kindness in action.

Why Color in Hiking Clothes Matters

Aside from visibility and vibrancy, wearing color in nature does something else: it connects you to your surroundings. Deep orange mirrors the Pacific Yew berries. Mossy green blends into pine. Bright blue reflects alpine lakes. And magenta highlights the wild raspberries. 

Your outfit becomes part of the story, and not just what you wore, but how you felt in it.

On our hike to Josphine Lake in Many Glacier, I wore a bold violet cargo skirt and a sky blue crop tanktop - not exactly “blend in with the woods” attire. But when I looked back at the photos later, it felt like a snapshot of confidence. I didn’t want to disappear, I wanted to remember what it felt like to be fully in my body, grounded and proud and playful. That color helped me do that. And the cherry on top? I got three compliments on my outfit while out on the trail that day!

What to Pack for an Autumn Road Trip

If you’re planning a week long fall getaway like ours, here’s what I recommend packing:

• 3-4 tanks in your color palette

• 3-4 hiking shorts (biker short, high waster, runner shorts, etc.)

• 2 pants: one for hiking, one for relaxing

• 1–2 outer layers (jacket + cardigan or hoodie)

• 1 pair versatile sneakers or boots

• 1 dress that doesn’t wrinkle and makes you feel wow! 

• Accessories: claw clip, sunglasses, lip balm, portable charger, sunscreen (and bear spray if you’re going to Glacier!)

• A bold lip color for the town night (optional, but confidence-boosting!)

• A cozy scarf, wrap, or beanie for warmth and style

Packing Psychology Tip: Choose clothes that reflect how you want to feel - empowered, curious, comfortable, adventurous, zen, peaceful. Packing with intention (not fear of being unprepared) reduces stress, boosts confidence, and encourages you to be in the moment, not worrying about it. 

Final Thoughts

Autumn isn’t just a season, it’s a feeling. A shift. A softness. A reminder that change is a constant and an opportunity. Whether you’re hiking to hidden lakes or strolling past rustic storefronts, what you wear should enhance the experience, not hold you back.

And you don’t need a Pinterest-perfect wardrobe to do that.

The next time you’re packing for an adventure, remember this: you don’t need separate outfits for every part of the day, you need pieces that make you feel good from trailhead to town. Clothes that support your body, reflect your story, and bring a little joy into every snapshot.

What About You?

Do you have a go-to hiking outfit that makes you feel strong and stylish? Or a fall staple you never travel without?

Drop it in the comments below, I love hearing what makes you feel fabulous out in the wild. And if you’re trying to figure out how to build a fall travel wardrobe that works with your story, I’d love to help. 🧡

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