Theory:

You could have felt more comfortable wearing a white dress in summer and a black dress in winter, Have you ever wondered why? Now let us take a look into how heat in different seasons affects our clothing patterns.
A hot summer:
During the summer, we know that the heat from the sun will be high. So, we used to feel more heat. In these times, if we dress light-coloured clothes like white colour, we feel comfortable.
 
Because the light-coloured clothes are capable of reflecting most of the Sun's radiation that falls on them, therefore, we feel more comfortable wearing them in the summer. We may feel discomfort wearing dark-coloured clothes because dark colour clothes tend to absorb the Sun's radiation.
 
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Fig. - Hot summer
A cold winter:
During the winter season, the earth receives less amount of heat from the sun; which is why we feel so cold in winter times.
 
And if we dress in dark-coloured clothes like black in this season, we feel more comfortable.
 
These dark-coloured clothes are capable of absorbing more heat. And, when an object absorbs heat, its temperature will rise. So, if we dress in these coloured clothes in winter, we will feel comfortable in a heavy cold time like winter.
 
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Fig. - Cold winter
 
And in the winter season, we used to wear woollen clothes because the these clothes are poor conductors of heat, which oppose the penetration of outside cold to our body. And that's why we feel more comfortable wearing woollen clothes in the winter.