Yes

you do need a jacket based on the weather in Milwaukee, WI, USA 1 second ago

Why? Because it's cold enough to freeze the brass off a bald monkey and it's so windy, you’re practically horizontal just trying to walk!
5°F-15°C & Windy

Wind is 17 mph28 km/h from the West, gusting to 30 mph49 km/h
December 12
5am5°F-15°C18 mph29 km/h WestWindy
6am5°F-15°C17 mph28 km/h WestWindy
7am5°F-15°C17 mph27 km/h WestWindy
8am4°F-15°C16 mph26 km/h WestWindy
9am5°F-15°C15 mph25 km/h WestWindy
10am6°F-14°C15 mph24 km/h WestMostly Clear
11am8°F-13°C14 mph23 km/h WestMostly Clear
12pm10°F-12°C14 mph22 km/h WestPartly Cloudy
1pm12°F-11°C13 mph21 km/h WestPartly Cloudy
2pm14°F-10°C12 mph20 km/h WestMostly Clear
3pm15°F-10°C12 mph20 km/h WestMostly Clear
4pm15°F-9°C12 mph19 km/h WestMostly Clear
DateLowHighWindDayNight
December 124°F-15°C15°F-9°C13 mph20 km/h from WestMostly ClearClear
December 138°F-14°C28°F-2°C5 mph9 km/h from EastPartly CloudyMostly Cloudy
December 1428°F-2°C40°F4°C15 mph24 km/h from SoutheastDrizzleRain
December 1537°F3°C43°F6°C6 mph10 km/h from SouthCloudyCloudy
December 1636°F2°C45°F7°C10 mph16 km/h from SouthRainRain
December 1726°F-3°C37°F3°C15 mph24 km/h from NorthwestPartly CloudyMostly Cloudy
December 1823°F-5°C30°F-1°C7 mph11 km/h from NorthwestMostly CloudyPartly Cloudy

Yes

Low of 8°F-14°C, High of 28°F-3°C
Wind: 5 mph9 km/h
Precipitation: None

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