The late autumn wind always carries a sense of calm and slowness. Leaves along the streets turn from yellow to red, and the sky darkens earlier and earlier. Quietly, I shift from lightweight knits and thin trench coats to heavier wardrobe pieces. For me, the true sign of autumn isn’t just the appearance of a coat—it’s the moment I put on that pair of tall boots. The elongated silhouette from the ankle up, the warm embrace around the calves, and the meticulous styling that complements the boots—only then do I truly feel that I’ve stepped into deep autumn.
This season, I’ve been obsessed with three outfits. They’re practical yet refined, perfect for daily wear, commuting, or even a casual date. Starting from the boots downward, let me walk you through my favorite, most frequently worn deep autumn ensembles.
Look One: Knee-High Boots × Wool Mini Skirt × Earth-Toned Tweed Coat
Keywords: Academic elegance, British tones, defined layering
This is my ultimate go-to look for the start of late autumn. Whenever I meet friends for coffee, stroll through weekend markets, or simply want to look put-together on a regular outing, I naturally reach for these few pieces.
The boots are a pair of caramel-brown leather knee-highs with a structured shaft that flatters the leg line. I especially love how they work with mini skirts—leaving just a sliver of skin between boot and hem adds a touch of lightness and prevents the outfit from feeling too heavy.
The mini skirt is navy blue with a plaid pattern, A-line cut, and hits about two-thirds down the thigh. It adds a touch of preppy charm. Underneath, I usually wear a fine-knit turtleneck in cream, camel, or mist gray—hues that look soft under the autumn light and carry a quiet, vintage-film kind of mood.
The most defining piece is the earth-toned tweed coat I brought back from Italy. It’s from a heritage brand and has a boxy silhouette. The hem hits just below the skirt, thick without being bulky. Its structured shoulders give an unspoken air of presence. Once, while walking through Paris in this look, a stranger stopped me just to ask where the coat was from—I secretly delighted in that moment all day.
I often pair it with leather gloves and vintage-style metal earrings, channeling that old-movie student aesthetic. This look is ideal for clear, slightly chilly days when you want warmth without compromising city style.
Look Two: Mid-Calf Boots × Knit Dress × Belted Trench Coat
Keywords: Minimalist lines, soft textures, urban elegance
This outfit is my most effortless late autumn solution. On mornings when I don’t have time to deliberate in front of the mirror, it’s my go-to. Reliable, refined, and always works.
I start with a knit dress as the centerpiece. The fabric needs to have some drape—smooth and cozy without adding bulk. My go-to colors this year are deep moss green and cocoa gray. I prefer a mid- to high-waist cut that softly defines the figure without clinging too tightly.
The boots are minimalist black mid-calf ones with a round toe and low heel. The shaft fits snugly but not tightly—no squeaking when walking, just smooth strides through city streets. I found these on Amazon; they’re from an Italian brand, buttery-soft leather, and remarkably comfortable for all-day wear.
My trench coat is a staple for all of autumn, but for deep autumn, I go for a heavier, warmer version. I love belted trenches in camel or burnt caramel shades—they effortlessly create that “coat flowing in the wind, but you remain composed” look.
To add layering and detail, I sometimes wear a crisp white shirt underneath the knit dress, letting the collar and cuffs peek out. It’s an easy trick for extra polish and outfit variation.
I usually pair this look with a structured small shoulder bag, a metallic wristwatch, and sunglasses. The result is sleek and refined—perfect for gallery visits, afternoon tea, or a solo library session.
Look Three: Slouch Boots × Straight-Leg Jeans × Cashmere Overcoat
Keywords: Relaxed chic, cool-toned streetwear, winter-transition ready
In the latter half of deep autumn, temperatures drop fast. On windy days, I already start missing my winter scarves. That’s when I shift to a more winter-leaning outfit—but still hold on to the freedom of fall.
The key to this look is my pair of slouchy grey-taupe boots. They have a soft, rumpled look with a slightly wider shaft, offering a relaxed silhouette without squeezing the legs. This design is perfect with denim. Every time I walk in these boots over crunchy leaves, it feels like I’ve stepped into a film frame.
The jeans are mid-to-high-rise, straight-leg, and long enough to slightly cover the boot top. I go for soft gray or smoky blue washes—they’re especially stunning in fall’s muted light and perfectly complement the boots’ tones. On top, I’ll wear a soft wool turtleneck in ivory or light camel, often paired with a draping cashmere scarf. The whole vibe is effortlessly stylish, like someone who casually stepped out but still looks thoughtfully dressed.
The overcoat is always a heavyweight cashmere one. Mine is a navy H-line cut with dropped shoulders and a wide waist belt. It’s quietly luxurious and wraps you like a seasonal cocoon. It doesn’t shout for attention, but up close, it radiates quality.
If I’m planning to be out longer, I’ll top off the outfit with a wool hat and a leather structured tote. This look is ideal for city evenings—whether it’s an art show, a cozy bookstore, or an open-air wine bar.
Tall Boots: The Beginning of Autumn’s Texture
Every time the seasons shift, I find myself revisiting the idea of personal style. Not everyone needs to chase trends, but I believe everyone should find a way to maintain their own rhythm and warmth as the weather changes. For me, tall boots are more than a wardrobe staple—they are a symbol of seasonal transition, a cue to step forward into the colder months with intention and comfort.
These three outfits have accompanied me throughout late autumn. They’re my most trusted uniforms, day in and day out. The moment I zip up those boots, I know—autumn has arrived, and I’m ready for it.
