Yes

you do need a jacket based on the weather in Southold, NY, USA 1 second ago

Why? Because it's cool. Pleasantly cool, but cool!
56°F13°C & Mostly Clear

Wind is 10 mph16 km/h from the Northwest, gusting to 14 mph22 km/h
October 25
11pm56°F13°C11 mph17 km/h NorthMostly Clear
October 26
12am56°F13°C10 mph16 km/h NorthPartly Cloudy
1am55°F13°C11 mph17 km/h NorthMostly Cloudy
2am55°F13°C11 mph17 km/h NorthCloudy
3am55°F13°C10 mph17 km/h NorthMostly Cloudy
4am54°F12°C10 mph16 km/h NorthCloudy
5am54°F12°C10 mph16 km/h NorthCloudy
6am54°F12°C8 mph14 km/h NorthMostly Cloudy
7am54°F12°C8 mph14 km/h NorthPartly Cloudy
8am53°F12°C9 mph14 km/h NorthPartly Cloudy
9am53°F12°C9 mph14 km/h NorthPartly Cloudy
10am52°F11°C9 mph15 km/h NorthPartly Cloudy
DateLowHighWindDayNight
October 2550°F10°C57°F14°C9 mph15 km/h from NorthwestMostly ClearMostly Cloudy
October 2651°F10°C56°F13°C8 mph12 km/h from NorthMostly ClearMostly Clear
October 2747°F8°C53°F12°C8 mph14 km/h from NortheastMostly ClearMostly Clear
October 2848°F9°C55°F13°C19 mph31 km/h from NortheastWindyWindy
October 2949°F9°C55°F13°C16 mph26 km/h from NortheastDrizzleWindy
October 3051°F11°C59°F15°C26 mph42 km/h from EastRainHeavy Rain
October 3154°F12°C59°F15°C19 mph30 km/h from SouthwestWindyWindy

Yes

Low of 51°F11°C, High of 56°F14°C
Wind: 8 mph12 km/h
Precipitation: None

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