I'm going to be hanging out with a guy i like for a few days. I am from a warm climate so i don't have any winter clothes so i need to purchase some since he lives in the north. What would you prefer a girl to wear during a casual hang out. A dress with leggings, jeans, sweaters, yoga pants, sweat shirts, boots, sneakers, heels… I am rather slim but have a really nice butt. What kind of winter close do you think would be the best?
Jeans and a sweatshirt is fine. Whatever makes the girl comfortable. I feel like if she's comfy then we can go anywhere and do anything. We can take long walks because she ain't wearing heels, and cuddling also feels better.
Be yourself or change to a certain degree that you can cope with - ask whether you can keep this up in the long term.
Whatever keeps you warm - it turns the mood (bad attempt at neutral phrasing) when a girl is cold with all her face red. We would rather see some girl warm than freezing in very exposed clothing. Ultimately, @Virulent is right - we care more about how you make us feel with your facial features.