Yes

you do need a jacket based on the weather in Pleasantville, NY 10570, USA 51 seconds ago

Why? Because sorry, it's too cool for just a hoodie!
52°F11°C & Cloudy

Wind is 6 mph9 km/h from the East, gusting to 15 mph24 km/h
May 21
2am52°F11°C7 mph11 km/h SoutheastPartly Cloudy
3am53°F12°C8 mph13 km/h SoutheastCloudy
4am52°F11°C9 mph14 km/h SoutheastCloudy
5am52°F11°C9 mph14 km/h SoutheastCloudy
6am51°F11°C8 mph14 km/h EastCloudy
7am51°F10°C8 mph13 km/h EastCloudy
8am51°F10°C9 mph15 km/h EastCloudy
9am52°F11°C9 mph14 km/h EastCloudy
10am53°F12°C9 mph15 km/h EastCloudy
11am54°F12°C10 mph16 km/h EastCloudy
12pm54°F12°C10 mph16 km/h EastCloudy
1pm55°F13°C10 mph16 km/h EastCloudy
DateLowHighWindDayNight
May 2148°F9°C55°F13°C10 mph15 km/h from EastDrizzleRain
May 2245°F7°C51°F10°C11 mph18 km/h from NortheastRainDrizzle
May 2344°F6°C57°F14°C4 mph7 km/h from WestDrizzleDrizzle
May 2447°F8°C61°F16°C11 mph17 km/h from WestMostly CloudyPartly Cloudy
May 2549°F9°C66°F19°C9 mph14 km/h from NorthwestMostly CloudyMostly Clear
May 2649°F9°C69°F21°C5 mph8 km/h from WestMostly CloudyMostly Cloudy
May 2753°F11°C68°F20°C6 mph10 km/h from EastRainPartly Cloudy

Yes

Low of 45°F7°C, High of 51°F11°C
Wind: 11 mph18 km/h
Precipitation: 92% rain

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