Layered looks with lots of (stain-resistant) personality
It’s the start of November. The clocks just fell back, and the last remnants of warm-ish weather are holding on for dear life. I am writing to you from my cozy corner of a home office with a hot ginger tea and even stronger opinions about layering.
Autumn is, without question, my favorite season for clothes. It’s also the most variable in terms of weather and, therefore, the most logistically demanding.
Most days, I bundle up to start my commute alongside the morning frost. Then I peel off all my layers by noon, but I am back to wearing blanket scarves after the sun goes down. Add in the wind, rain, crowded buses, overheated cafes, and grassy lawns that turn to mud overnight, and getting dressed feels like a feat of engineering.
For context, I’m petite (a towering 5’1”), and I walk at least 11,000 steps a day, whether rain or shine. I also love to travel and go hiking every chance I can. I shop secondhand whenever possible, and I try to stick to natural fibers because they breathe more efficiently, feel better on my skin, and are more durable than their synthetic counterparts. I treat my wardrobe as a creative extension of myself but, above all else, I prioritize comfort and practicality because I live such an active lifestyle.
All that to say, I’ve intentionally curated a fall wardrobe that can handle any weather, pack down into a carry-on, keep me both warm and cool, and also look presentable enough to make a great first impression.
Let’s dive into the six foundational aspects of my Autumnal wardrobe.
1: Merino Wool
This is the hardest-working fiber in my closet, yet it’s surprisingly easy to find second-hand.
Merino wool is how I stay comfortable all day long, even though I always run cold indoors but walk everywhere outdoors. This fiber is incredible at regulating my body temperature. It insulates me from cold winds, feels breathable along every step of a long walk, wicks away moisture, and resists odor. As such, I often wear the same merino sweater throughout a full weekend of travel without ever worrying about laundry.
It’s also a perfect match for my petite frame. Fine-gauge merino gives incredible warmth with hardly any bulk so I can stay comfortable without appearing overwhelmed by fabric.
I have one chunkier merino wool sweater that I wear in the late fall / early winter, but most of my merino pieces are thin socks, tight base layers, and light pullovers. A current favorite is the Oasis line of Merino base layers from Icebreaker.
2: Loose Bottoms
I love getting the most wear possible out of everything in my closet. So I transition all of my jeans, flowy trousers, and maxi skirts from summer into fall.
On cold mornings, I can easily throw on a pair of tights or thermal leggings underneath these loose silhouettes. Then, when the mid-day warmth arrives, my base layers take up virtually zero room in my bag.
This time of year, I reach for bottoms in both fluid fabrics like viscose as well as heavier cottons. A midi skirt with boots and a lightweight sweater has been my favorite combination for the office, while a maxi dress with a cropped cardigan is perfect for long travel days.
With all loose clothing, I keep a few caveats in mind to compliment my petite frame.
Re: maxi skirts, I always try to style around a defined waist, opt for vertical stripes or pleats to elongate, and shorten the hems so they don’t drag through sidewalk puddles.
Straight-leg jeans also elongate my legs, and that illusion of length is much appreciated. All of my jeans are vintage or thrifted, and at least 98% cotton for maximum durability. I’ve gotten really good at hemming them to hit at the perfect spot for all my favorite shoes. I haven’t bought into the barrel-leg denim trend, but I’m sure they would be great for layering thermals underneath.
In terms of flowy trousers, I opt for wool- or linen-blends when I want nice movement as well as heavy cotton twills for more durability. (The Big Bud Press work pants are a favorite.)
High-waisted styles are preferred for my specific proportions because they visually lengthen my legs and look great with all my cropped jackets.
3: Light Jacket + Big Scarf
This combo is my solution to the daily struggle of “It’s chilly, but I’m also in for a long walk.”
I rarely wear a super heavy coat in the fall because I commute by bus, walk a ton, and have to carry everything I need for the day. Big puffers, though the persistent desire when I’m waiting for the bus, quickly become too stuffy and cumbersome as soon as I step inside. Then there’s the challenge of storing or transporting this massive coat that I no longer need by mid-day. I much prefer to wear a light jacket and adjust everything inside or outside of my outerwear.
Though trendy, mid-calf styles like full-length trenches often swallow my frame. Instead, I prioritize jackets that end at a few key positions: My waist, my hips or just above my knees.
I thrifted a cropped wool jacket (with fun, sparkly threads) a while back and that’s my current favorite. I also have a 100% cotton chore jacket (with multiple massive pockets) in a fun olive green color. I’ve been meaning to wax it to make it waterproof.
When I really want to bundle up without the bulk, I opt for my hooded puffer with synthetic down fill. It’s waterproof and I can double up with my down-filled vest underneath for maximum warmth.
The first two options fit inside my rain parka, and all three options pair beautifully with my ever growing collection of massive scarves.
Scarves are my most versatile accessory. I buy them big enough to wrap around my neck and head during a frosty morning, fold around my body as a make-shift vest or shawl in a cold building, or lay across my lap as a blanket on a long flight.
I can stay warm in a lighter jacket because my scarves do the heavy lifting. Plus, scarves offer incredible opportunities to experiment with color and print.
Section 4: Funky Tights
Speaking of color and print! Tights are small but mighty ways to express your creativity.
I’ve loved funky tights since I was a teenager. (Fun fact: I wrote a weekly column in high school called The Girl in the Yellow Tights.) In addition to feeding my soul, funky tights help to break up all the solid neutrals in my every day fall wardrobe.
I have tights in ribbed textures, bold colors, subtle patterns, sheer sparkles, and polka dots. They add personality to a khaki skirt or black dress, and they add warmth too, which is a nice bonus when you’re trying to survive a 32-degree morning.
Tights are also petite-friendly. I love pairing black tights with my black Chelsea boots to create a continuous line from hem to shoe, which visually lengthens my legs. Conversely, a statement tight under a knee-high boot draws the eye down in a fun way.
Section 5: Waterproof Footwear
In my summer wardrobe post, I mentioned that capable footwear is non-negotiable for me. That standard gets even higher as summer turns to fall because, where I live, Autumn is synonymous with rain.
I struggle with classic, rubber rain boots. They are often flimsy and lack the comfort for the amount of mileage I cover on a daily basis. Plus, they cut off at an awkward point on my calves.
Instead, I wear leather Chelsea boots that go over my ankles or my lace-up hiking boots with waterproof, Gore-Tex coating. My current shoe rotation also includes waterproof trail runners, leather loafers with a high vamp, and my barefoot sneakers for the cloud-free days.
Real leather, when properly treated with a good wax or spray, is water-resistant and only looks better with age. I often find leather footwear secondhand in excellent condition. I scored a pair of black leather oxfords, new with tags, for less than the cost of a new pair of tights. (And that’s saying something.)
I love a tall boot, too, but have yet to find a short-friendly option. If you have suggestions for a thigh or mid-calf boot, hit your girl up! (Bonus points if it’s in a fun color like burgundy.)
Section 6: Pops of Red
This all started when I thrifted a cherry red, leather skirt.
I fell in love with that piece, even though everything about it fell outside my comfort zone. Still, it called to me. So I brought it home and learned that I love styling it with a fully neutral outfit.
After that discovery, I started incorporating other pops of red into my wardrobe.
My favorite scarf is in a muted red that borders on orange. It pairs beautifully with my olive chore jacket and my cropped wool jacket.
I recently bought a bunch of thin crew socks in solid colors, one of which is cherry red. I love how a basic jeans + loafer combo looks with that small pop of red.
The only floral piece I’ve carried into fall is my navy blouse with flowy sleeves and small cherry red flowers.
And let’s not forget burgundy, which is perhaps my favorite shade of red. I have a thin turtleneck that I wear under all my pinafore dresses, as well as burgundy sweater tights for the colder fall days.
This Wardrobe Is Road-Tested
Autumn dressing is a breeze because I’ve built a system of pieces that seamlessly mix-and-match, adapt to fluctuating temperatures, and balance functionality with creative expression.
Since I’m petite, I pay attention to proportions, and I’ll never stop hemming things. I also prefer secondhand shopping and that means that I have to be patient, but the quality is always better than what I find at the mall.
I’ve gradually built up a solid foundation of natural fibers that keep me warmer, drier, and more comfortable than acrylic yarns and synthetic textiles.
Every piece I own has earned its spot. My clothes carry me through life, and my life is full of walking, hiking, and traveling so you best believe I put my clothes through the ringer.
Now let’s soak up the last few weeks of fall!
Enjoyed this post? There's a whole lot more waiting for you!
Subscribe to my Substack for travel tips, inspirational essays, ethical travel takes, and real talk about freelancing finances, all delivered straight to your inbox.
No spam. Just stories.