Yes

you do need a jacket based on the weather in Regina, SK, Canada 1 second ago

Why? Because the wind is harsh and biting!
63°F17°C & Clear

Wind is 13 mph21 km/h from the Southeast, gusting to 22 mph36 km/h
October 10
9pm61°F16°C14 mph23 km/h SoutheastClear
10pm60°F15°C15 mph25 km/h SoutheastWindy
11pm58°F15°C17 mph27 km/h SoutheastWindy
October 11
12am58°F14°C18 mph29 km/h SoutheastWindy
1am57°F14°C19 mph30 km/h SoutheastWindy
2am56°F14°C17 mph28 km/h SoutheastWindy
3am56°F13°C17 mph27 km/h SoutheastWindy
4am55°F13°C17 mph28 km/h SoutheastWindy
5am55°F13°C17 mph27 km/h SoutheastWindy
6am54°F12°C17 mph27 km/h SoutheastWindy
7am54°F12°C16 mph26 km/h SoutheastWindy
8am53°F12°C15 mph25 km/h SoutheastWindy
DateLowHighWindDayNight
October 1030°F-1°C69°F21°C11 mph18 km/h from SoutheastClearWindy
October 1153°F12°C74°F23°C12 mph19 km/h from SouthMostly ClearRain
October 1233°F1°C56°F13°C21 mph33 km/h from NorthwestRainFlurries
October 1329°F-2°C40°F5°C6 mph10 km/h from NorthwestMostly CloudyMostly Cloudy
October 1428°F-2°C46°F8°C6 mph10 km/h from SoutheastPartly CloudyMostly Clear
October 1531°F-0°C52°F11°C8 mph13 km/h from SoutheastPartly CloudyPartly Cloudy
October 1641°F5°C51°F11°C7 mph11 km/h from NorthDrizzleDrizzle

Yes

Low of 53°F12°C, High of 74°F24°C
Wind: 12 mph19 km/h
Precipitation: None

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