Yes

you do need a jacket based on the weather in Oshawa (Windfields), Ontario, Canada 1 second ago

Why? Because it's raining in your area and it's cold enough that makes you wish you had a hat, but you're still too proud to admit it and it's fairly windy outside!
49°F10°C & Rain

Wind is 12 mph19 km/h from the East, gusting to 21 mph33 km/h
May 22
6pm49°F10°C12 mph19 km/h EastRain
7pm49°F9°C12 mph19 km/h EastRain
8pm49°F9°C11 mph17 km/h EastDrizzle
9pm48°F9°C8 mph13 km/h EastDrizzle
10pm48°F9°C8 mph13 km/h EastDrizzle
11pm48°F9°C7 mph12 km/h EastDrizzle
May 23
12am47°F9°C8 mph12 km/h EastDrizzle
1am47°F8°C8 mph13 km/h EastDrizzle
2am46°F8°C7 mph12 km/h EastDrizzle
3am46°F8°C7 mph12 km/h EastDrizzle
4am46°F8°C7 mph11 km/h EastDrizzle
5am46°F8°C5 mph9 km/h EastRain
DateLowHighWindDayNight
May 2243°F6°C49°F10°C13 mph20 km/h from EastRainRain
May 2346°F8°C51°F11°C5 mph8 km/h from NorthwestRainDrizzle
May 2445°F7°C58°F14°C12 mph19 km/h from NorthwestDrizzlePartly Cloudy
May 2545°F7°C59°F15°C11 mph17 km/h from NorthwestRainMostly Clear
May 2646°F8°C68°F20°C4 mph6 km/h from NorthwestPartly CloudyMostly Clear
May 2747°F9°C68°F20°C7 mph11 km/h from EastMostly CloudyMostly Cloudy
May 2850°F10°C64°F18°C11 mph17 km/h from EastDrizzleMostly Cloudy

Yes

Low of 46°F8°C, High of 52°F11°C
Wind: 5 mph8 km/h
Precipitation: 91% rain

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