Yes

you do need a jacket based on the weather in Paddockwood, SK S0J 1Z0, Canada 1 second ago

Why? Because the wind is offering free, unsolicited face massages!
69°F20°C & Cloudy

Wind is 10 mph16 km/h from the Southeast, gusting to 20 mph32 km/h
May 23
5pm69°F20°C10 mph17 km/h SoutheastMostly Cloudy
6pm69°F21°C10 mph16 km/h SoutheastMostly Cloudy
7pm69°F21°C10 mph16 km/h SoutheastMostly Cloudy
8pm69°F20°C10 mph16 km/h SoutheastMostly Clear
9pm67°F20°C10 mph15 km/h SoutheastPartly Cloudy
10pm64°F18°C8 mph12 km/h SoutheastPartly Cloudy
11pm60°F16°C6 mph9 km/h SoutheastMostly Cloudy
May 24
12am57°F14°C5 mph8 km/h SoutheastPartly Cloudy
1am56°F13°C5 mph7 km/h SoutheastPartly Cloudy
2am53°F11°C6 mph10 km/h EastMostly Cloudy
3am51°F10°C6 mph9 km/h SoutheastMostly Cloudy
4am49°F10°C5 mph9 km/h SoutheastPartly Cloudy
DateLowHighWindDayNight
May 2340°F5°C69°F21°C9 mph14 km/h from SoutheastPartly CloudyPartly Cloudy
May 2445°F7°C72°F22°C8 mph14 km/h from SouthPartly CloudyMostly Clear
May 2547°F8°C74°F23°C12 mph19 km/h from SouthMostly ClearClear
May 2651°F11°C77°F25°C15 mph24 km/h from SouthClearClear
May 2751°F11°C76°F25°C14 mph23 km/h from SouthClearMostly Clear
May 2853°F12°C80°F27°C9 mph14 km/h from SouthwestPartly CloudyMostly Clear
May 2954°F12°C83°F28°C9 mph14 km/h from SouthwestClearClear

Yes

Low of 46°F8°C, High of 72°F22°C
Wind: 8 mph14 km/h
Precipitation: None

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