Stage Lighting And Effects Equipment

I am going tomorrow morning to meet a guy I like (he knows I do) for coffee, and it's been raining a lot where I am so tomorrow I was going to wear a dark brown coat with a darkish but colorfully striped scarf and my black rain boots with rainbow stars--it's mostly the boots that I'm wondering about, because I don't know if they would look really young (I'm a high school junior, but people say I could look like I'm 20 when I wear work-dressy clothing), or if they would seem girly in a good feminine way (I'm generally not so feminine in that I don't wear pink) or girly in an annoying, giggling kid kind of way.

I know this is confusing, but I'm paranoid--I dunno if guys get slightly intimidated by the mature look (I have almost black hair and very pale skin, so I don't have that baby blonde look) and if it's good to balance that with starry rain boots or if it's better to wear my nicer shoes so I can still wear the scarf.