Yes

you do need a jacket based on the weather in Winnipeg, MB, Canada 1 second ago

Why? Because it's cool. Pleasantly cool, but cool and it's really really huffing out there!
53°F12°C & Windy

Wind is 17 mph28 km/h from the South, gusting to 36 mph58 km/h
October 26
4am53°F12°C17 mph28 km/h SouthWindy
5am53°F12°C16 mph26 km/h SouthWindy
6am52°F11°C16 mph25 km/h SouthWindy
7am52°F11°C16 mph25 km/h SouthWindy
8am51°F10°C15 mph24 km/h SouthWindy
9am50°F10°C15 mph25 km/h SouthWindy
10am51°F10°C16 mph26 km/h SouthWindy
11am50°F10°C16 mph26 km/h SouthWindy
12pm51°F10°C17 mph27 km/h SouthWindy
1pm51°F11°C18 mph28 km/h SouthWindy
2pm52°F11°C19 mph30 km/h SouthWindy
3pm53°F12°C20 mph32 km/h SouthWindy
DateLowHighWindDayNight
October 2537°F3°C61°F16°C14 mph22 km/h from SouthMostly ClearWindy
October 2650°F10°C61°F16°C20 mph32 km/h from SouthWindyCloudy
October 2748°F9°C57°F14°C9 mph15 km/h from SouthRainRain
October 2841°F5°C49°F10°C9 mph14 km/h from NorthwestRainPartly Cloudy
October 2936°F2°C49°F9°C5 mph7 km/h from NorthwestPartly CloudyPartly Cloudy
October 3036°F2°C51°F10°C8 mph13 km/h from SouthwestPartly CloudyPartly Cloudy
October 3134°F1°C48°F9°C5 mph8 km/h from NorthwestMostly ClearPartly Cloudy

Yes

Low of 50°F10°C, High of 62°F17°C
Wind: 20 mph32 km/h
Precipitation: None

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