Yes

you do need a jacket based on the weather in Orangeville, ON L9W, Canada 1 second ago

Why? Because some drizzle out there and it's not very warm out and it's so windy, your hat has officially retired from your head!
52°F11°C & Drizzle

Wind is 13 mph21 km/h from the South, gusting to 25 mph40 km/h
March 31
2am53°F11°C15 mph24 km/h SouthwestCloudy
3am53°F12°C16 mph25 km/h SouthwestWindy
4am52°F11°C16 mph25 km/h SouthwestWindy
5am52°F11°C15 mph24 km/h SouthwestCloudy
6am52°F11°C14 mph22 km/h SouthwestDrizzle
7am50°F10°C13 mph21 km/h WestCloudy
8am48°F9°C13 mph21 km/h WestCloudy
9am47°F8°C16 mph25 km/h WestWindy
10am45°F7°C16 mph26 km/h WestWindy
11am42°F5°C16 mph26 km/h WestWindy
12pm39°F4°C16 mph25 km/h WestWindy
1pm37°F3°C16 mph25 km/h WestWindy
DateLowHighWindDayNight
March 3129°F-2°C53°F12°C15 mph24 km/h from WestCloudyMostly Cloudy
April 123°F-5°C35°F2°C9 mph15 km/h from NorthMostly ClearMostly Cloudy
April 225°F-4°C43°F6°C17 mph27 km/h from EastHeavy SnowRain
April 338°F3°C59°F15°C17 mph27 km/h from WestWindyMostly Cloudy
April 433°F1°C51°F11°C7 mph12 km/h from NorthwestPartly CloudyMostly Cloudy
April 532°F0°C48°F9°C7 mph12 km/h from NortheastCloudyDrizzle
April 632°F0°C45°F7°C10 mph17 km/h from WestDrizzlePartly Cloudy

Yes

Low of 23°F-5°C, High of 35°F2°C
Wind: 9 mph15 km/h
Precipitation: None

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