Yes

you do need a jacket based on the weather in North York, Toronto, ON, Canada 4 minutes ago

Why? Because it's pretty chilly!
55°F13°C & Cloudy

Wind is 6 mph9 km/h from the South, gusting to 18 mph29 km/h
October 18
1pm56°F13°C6 mph10 km/h SouthMostly Cloudy
2pm59°F15°C8 mph13 km/h SouthPartly Cloudy
3pm60°F15°C8 mph13 km/h SouthMostly Cloudy
4pm62°F17°C10 mph15 km/h SouthMostly Clear
5pm64°F18°C10 mph16 km/h SouthMostly Cloudy
6pm67°F19°C10 mph16 km/h SouthMostly Clear
7pm68°F20°C10 mph16 km/h SouthMostly Cloudy
8pm68°F20°C10 mph15 km/h SouthMostly Cloudy
9pm68°F20°C9 mph14 km/h SouthMostly Cloudy
10pm66°F19°C7 mph12 km/h SouthMostly Cloudy
11pm64°F18°C6 mph9 km/h SouthMostly Cloudy
October 19
12am63°F17°C5 mph8 km/h SouthMostly Cloudy
DateLowHighWindDayNight
October 1851°F11°C68°F20°C8 mph13 km/h from SouthMostly CloudyMostly Cloudy
October 1955°F13°C71°F21°C12 mph19 km/h from SouthRainRain
October 2048°F9°C59°F15°C13 mph20 km/h from NorthwestDrizzleMostly Clear
October 2145°F7°C55°F13°C9 mph14 km/h from SouthRainMostly Cloudy
October 2243°F6°C52°F11°C7 mph12 km/h from SouthwestMostly CloudyDrizzle
October 2341°F5°C52°F11°C9 mph15 km/h from WestDrizzlePartly Cloudy
October 2438°F4°C53°F12°C6 mph9 km/h from WestMostly CloudyDrizzle

Yes

Low of 55°F13°C, High of 71°F22°C
Wind: 12 mph19 km/h
Precipitation: 65% rain

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