New York has turned cold, and the street style has changed with it. On 6 October 2026, Olivia Rodrigo, in the middle of her Unraveled Tour, took a day off to run errands in the city, and her outfit is a near-perfect answer to the question of what to wear when it's suddenly too cold for summer dresses.
The outfit, piece by piece
As spotted by Vogue, Rodrigo wore:
A black knit shawl sweater, worn slipping off the shoulder.
A striped long-sleeve tee layered underneath.
A pleated knee-length skirt with plenty of movement.
Chunky leather biker boots reaching just below the knee.
A Supervinyl cap, a nod to the well-known Hollywood record shop.
None of that is complicated. It works because of how the pieces balance each other.
Why "boho-grunge" works
Vogue called the look boho-grunge, and the name is spot on. The off-the-shoulder shawl and the swishy skirt are the free-spirited, boho half. The heavy biker boots, black knitwear and the record-shop cap are the grunge half. Each side keeps the other in check: the skirt stops the boots from feeling too harsh, and the boots stop the skirt from looking too sweet.
Mixing sweet and tough has always been Rodrigo's thing. She moves between retro babydoll dresses and vintage punk T-shirts, often in the same week. This outfit simply takes that instinct into autumn layers, and it's easy to copy because most of us already own at least half of it.
How to wear boho-grunge this autumn
1. Start with a soft, oversized knit
A chunky shawl-collar cardigan or wrap sweater in black or charcoal. Size up so it can slip off one shoulder. Look for a heavy, slightly textured knit. Fine merino won't drape the same way.
2. Layer a stripe underneath
A striped long-sleeve tee adds a bit of pattern and a slightly retro, indie edge. Navy-and-white or black-and-white Breton stripes are easiest. Let the cuffs show at the wrist.
3. Add a skirt that moves
A pleated knee-length skirt, in a plain colour or a muted check, adds the swish. The knee length matters: it leaves just enough leg showing between hem and boot.
4. Ground it with biker boots
This is the piece that makes the look. Choose leather biker or engineer boots with a chunky sole, ideally reaching mid-calf or just below the knee so they almost meet the hem. Scuffed and worn-in beats shiny and new.
5. Finish with something personal
Rodrigo's Supervinyl cap is the detail that makes the outfit feel like hers. Do the same: a cap from a band, a local shop or a favourite place, a vintage tote, or a few silver rings.
Proportion tips
Volume on top, shape below: if the knit is very big, make sure the skirt has a defined waist.
Close the gap: a small stretch of leg between skirt and boot looks deliberate. A big one breaks the line. In colder weather, add black opaque tights.
Stick to a dark base: black, charcoal and brown keep the mix of textures looking intentional.
Three ways to switch it up
1. Weekend: swap the skirt for loose straight jeans tucked into the boots, but keep the shawl sweater.
2. Office: a longer pleated midi skirt, a fine-gauge stripe and polished boots with a lower shaft.
3. Evening: lose the cap, wear the knit fully off one shoulder over a black slip and keep the boots.
Shopping list
Chunky black shawl-collar cardigan or wrap knit
Striped long-sleeve cotton tee
Pleated knee-length skirt with a defined waistband
Leather biker boots, mid-calf to knee height
A cap or accessory with a story behind it
The takeaway
Rodrigo's day-off look isn't about expensive pieces or perfect styling. It's about contrast. Put your sweetest piece next to your toughest one, keep the colours dark and the fabrics tactile, and you've got an autumn uniform that's comfortable, practical and still looks cool.
Source: Vogue, "Olivia Rodrigo's Fall Style? Call It Boho-Grunge", 6 October 2026.