Yes, you can.

But make sure you put on very thick leggings, and a pair of thick leg warmers/winter boots to protect your ankles. (Note: There's a difference between winter boots and the normal boots you wear in Singapore. Winter boots have much thicker lining.) If possible, get skirts that are made specially to be worn during winter, since the material is thicker and have better insulation. See Photo 1-3.

Also, remember to wear a thick coat outside, as illustrated in the second last photo.

Photos.

Winter skirt + Winter Leggings + Boots (which can't be seen here)

Winter skirt + Winter Leggings + Leg warmers.

Winter Skirt + Winter Leggings + Leg warmers (not obvious) + Winter boots

Winter coat.

Finally putting everything together. The temperature was about -20 degree Celsius when this photo was taken.

Hope this helps! =))

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