What to Wear in Chicago in Fall: Leather Jacket Outfits for Wind
Fall in Chicago can mean a warm September afternoon, a crisp October evening by the river and a raw November wind, sometimes in the same week. Here is what to wear in Chicago in fall, month by month, with layers that handle the wind and a genuine leather jacket or coat doing most of the work.
Quick answer: Plan for highs in the mid 70s in September, low 60s in October and upper 40s in November, with colder nights. Wear a light layer and a leather jacket early in the season, add a sweater and scarf in October, and switch to a leather coat, gloves and a hat by November.
Chicago fall weather by month
These are the 1991 to 2020 climate normals from the National Weather Service, measured at Chicago's main airport station. Areas right by the lake run slightly warmer than inland neighborhoods through late fall, because the water cools more slowly than the land, but the open shoreline is also where the wind feels strongest.
| Month | Average high | Average low | What to wear |
|---|---|---|---|
| September | about 76°F | about 57°F | Tee or shirt, light leather jacket for evenings |
| October | about 63°F | about 45°F | Sweater or flannel under a leather jacket, scarf |
| November | about 48°F | about 34°F | Thicker knit, lined jacket or leather coat, gloves, hat |
Rain is part of the season too, with roughly three inches or more of precipitation in an average September and October. The normal first freeze at that station arrives around October 19, so late October mornings can start near or below freezing even after a mild afternoon.
What to wear in Chicago in fall: the core layers
The trick is building an outfit you can adjust between a sunny sidewalk, a shaded street between tall buildings and a heated restaurant.
- Base: a tee, thermal or button-up shirt.
- Middle: a merino or cotton sweater, a flannel or a thin hoodie. Turtlenecks are excellent here because they close the gap at your neck.
- Outer: a genuine leather jacket from September to early November, then a leather coat once the highs drop into the 40s.
- Accessories: a scarf from October on, plus gloves and a hat in November.
A closed leather jacket cuts wind far better than an open-weave knit or a denim jacket, which is why it suits a lakefront city so well. Our guide to whether a leather jacket is windproof explains where drafts still get in and which collars, cuffs, liners and lengths help most.
September: light layers and evenings outside
Early September often still feels like summer, with warm afternoons and comfortable evenings. A tee and jeans are enough during the day. Carry a light leather jacket for patio dinners, lakefront walks after sunset and evening events, when temperatures settle into the upper 50s.
By late September, mornings get cooler. Wear the jacket open over a long-sleeve tee or a light shirt and keep the sweater for October.
October: leather jacket season
October is the month a leather jacket earns its place. Highs in the low 60s and lows in the mid 40s call for a sweater or flannel underneath and the jacket zipped when the wind picks up. Add a wool scarf in the second half of the month, when first frosts become likely.
How warm a leather jacket feels depends on its weight, lining and fit. If you are unsure whether yours is enough on its own, our guide on whether leather jackets are warm covers roughly what temperatures each type of jacket suits.
November: when to switch to a leather coat
November is when Chicago starts to feel like winter. Highs average in the upper 40s and lows in the mid 30s, and wind makes it feel colder still. This is the time to move from a hip-length jacket to a longer leather coat that covers your hips and upper legs, or to a jacket with a removable liner that you can add back for warmth.
These three pieces cover the season, from a racer with a zip-out liner to a belted-collar aviator and a long coat for late fall:
Men's Heavyweight Cowhide Racer Jacket with Zip-Out Liner
Women's Black Lambskin Aviator Jacket with Belted Collar
Men's Black Leather Coat with Detachable Collar
The Men's Heavyweight Cowhide Racer Jacket with Zip-Out Liner is a good example of a jacket that adapts: wear it without the liner in September and zip the liner back in as November arrives. For deeper cold, a coat with a collar you can turn up, like the Men's Black Leather Coat with Detachable Collar, keeps the wind off your neck.
Dressing for wind off the lake
- Close the gaps. Wind finds the neck and wrists first. Turn up your collar, wear a scarf and choose cuffs that sit close to the wrist.
- Zip up between buildings. Downtown streets can funnel wind, so a jacket that feels fine on a side street may need to be zipped on a corner.
- Layer thin, not bulky. Two thin layers under leather hold more warmth than one thick sweater that strains the shoulders.
- Cover your head. A beanie or flat cap makes a big difference by the lake in November.
What if it rains?
A light shower will not ruin a well-kept leather jacket. Shake off the water, blot it with a soft towel and let it dry naturally on a wide hanger, away from radiators and heaters. For a full day of steady rain, carry an umbrella or wear a rain shell on that day. Our guide to wearing a leather jacket in the rain explains exactly what to do if your jacket gets soaked.
Shoes for walking the city
Chicago is a walking city, and fall brings wet leaves, puddles and slick sidewalks. Leather Chelsea boots and lace-up boots with rubber soles are the best all-round pick. Clean leather sneakers are fine on dry September days. Skip light suede once the rain starts, and choose boots with good tread in November.
Chicago fall outfits for men and women
- Men, October weekend: gray crewneck sweater, dark jeans, brown leather jacket, brown lace-up boots.
- Men, November workday: merino turtleneck, wool trousers, black leather coat, black Chelsea boots, leather gloves.
- Women, September evening: striped tee, straight jeans, black leather jacket, ankle boots.
- Women, late October: ribbed turtleneck, midi skirt, knee boots, black aviator-style leather jacket, wool scarf.
FAQ
Is a leather jacket warm enough for Chicago in October?
For most October days, yes, with a sweater or flannel underneath. Highs average in the low 60s and lows in the mid 40s, so add a scarf for evenings and late in the month.
When do you need a winter coat in Chicago?
Most people move to a heavier coat in November, when average highs fall into the upper 40s and lows into the mid 30s. A leather coat over layers covers much of November; deep winter calls for more insulation.
What shoes should I pack for Chicago in the fall?
Pack one pair of comfortable leather boots with rubber soles for rain and long walks, and one pair of clean sneakers for dry days.
Is it windy in Chicago in the fall?
It can be, especially along the lakefront and between tall buildings downtown. Wind makes the air feel colder than the thermometer says, so close your collar and add a scarf.
Now you know what to wear in Chicago in fall: light layers in September, a leather jacket and sweater in October, and a longer coat by November. Browse our leather coats and trench coats to get ready for the colder end of the season.