Yes

you do need a jacket based on the weather in Winnipeg, MB, Canada 8 minutes ago

Why? Because it's fairly windy outside!
65°F18°C & Mostly Cloudy

Wind is 12 mph19 km/h from the Southwest, gusting to 24 mph39 km/h
September 16
8am65°F18°C12 mph19 km/h SouthwestPartly Cloudy
9am66°F19°C12 mph20 km/h WestPartly Cloudy
10am68°F20°C13 mph20 km/h WestPartly Cloudy
11am70°F21°C12 mph20 km/h WestPartly Cloudy
12pm73°F23°C12 mph20 km/h WestPartly Cloudy
1pm74°F23°C12 mph20 km/h WestMostly Clear
2pm75°F24°C12 mph19 km/h WestPartly Cloudy
3pm76°F24°C12 mph20 km/h WestPartly Cloudy
4pm76°F24°C13 mph21 km/h WestPartly Cloudy
5pm76°F24°C13 mph21 km/h WestPartly Cloudy
6pm75°F24°C12 mph19 km/h WestPartly Cloudy
7pm73°F23°C10 mph16 km/h NorthwestPartly Cloudy
DateLowHighWindDayNight
September 1662°F17°C76°F24°C12 mph19 km/h from WestPartly CloudyPartly Cloudy
September 1758°F14°C71°F22°C8 mph13 km/h from NorthPartly CloudyMostly Cloudy
September 1854°F12°C69°F20°C9 mph14 km/h from NortheastMostly CloudyDrizzle
September 1958°F14°C72°F22°C10 mph16 km/h from SoutheastRainRain
September 2058°F14°C70°F21°C8 mph13 km/h from SouthMostly CloudyMostly Cloudy
September 2159°F15°C74°F23°C7 mph12 km/h from SouthPartly CloudyMostly Clear
September 2257°F14°C70°F21°C11 mph18 km/h from WestPartly CloudyMostly Clear

Yes

Low of 57°F14°C, High of 71°F22°C
Wind: 8 mph13 km/h
Precipitation: 11% rain

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