I double cleanse when I feel like my skin needs it. I would definitely do so more during summer just because you tend to get more sweaty and grimey then. I don't wear make-up much but if I did wear make-up everyday I would double cleanse then too. So... to answer your question, probably less so in winter myself but there are reasons why you might want to.
Double cleansing ensures that makeup, sunscreen and dirt from the day is washed off. You should wear spf also in winter, so its therefore still beneficial to double cleanse in winter even if you do not wear makeup.
No skincare is required tho so you should do whatever you feel comfortable with!
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