Don't be too fancy in style and color. He doesn't need your attention, but he likes you to look comfortable. Don't dress up too deliberately.
In spring and autumn, I like girls to wear loose wool coats with shirts, slim jeans (small skirts are also good), sports shoes or skateboarding shoes.
In summer, you can wear simple T-shirts, shorts and sandals, which are cool and sexy.
In winter, I feel sorry for her cold. As long as she doesn't wear it, she can wear it as she likes. I don't require it.
Personally, I prefer this feeling.