Yes

you do need a jacket based on the weather in Winston-Salem, NC 27106, USA 1 second ago

Why? Because the cold's there, but it's just a reminder, not an invasion!
41°F5°C & Clear

Wind is 3 mph5 km/h from the Southwest, gusting to 9 mph14 km/h
October 21
11am41°F5°C3 mph5 km/h SouthwestClear
12pm41°F5°C4 mph6 km/h SouthwestClear
1pm47°F8°C5 mph8 km/h SouthwestClear
2pm54°F12°C7 mph11 km/h SouthwestClear
3pm60°F15°C7 mph12 km/h SouthwestClear
4pm65°F18°C7 mph12 km/h SouthwestClear
5pm69°F20°C8 mph13 km/h SouthwestClear
6pm72°F22°C8 mph13 km/h SouthwestClear
7pm73°F23°C9 mph14 km/h SouthwestClear
8pm74°F23°C10 mph16 km/h SouthwestClear
9pm73°F23°C10 mph15 km/h SouthwestMostly Clear
10pm71°F21°C8 mph13 km/h SouthwestMostly Clear
DateLowHighWindDayNight
October 2141°F5°C74°F23°C7 mph12 km/h from SouthwestClearMostly Clear
October 2247°F8°C66°F19°C10 mph16 km/h from WestClearClear
October 2340°F4°C66°F19°C8 mph13 km/h from WestClearClear
October 2438°F3°C64°F18°C5 mph8 km/h from NorthwestMostly ClearClear
October 2537°F3°C63°F17°C3 mph5 km/h from EastPartly CloudyMostly Cloudy
October 2643°F6°C63°F17°C5 mph7 km/h from EastMostly CloudyCloudy
October 2746°F8°C59°F15°C10 mph16 km/h from NortheastDrizzleMostly Cloudy

Yes

Low of 47°F9°C, High of 66°F19°C
Wind: 10 mph16 km/h
Precipitation: None

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