In terms of for the date, I think Sporty works best because it's practical for a high-activity event like exploring an amusement park. Doesn't look bad either.
A lot of people are talking about her as a tomboy, but I'm not actually sure that's her personality. She's described it as a defense mechanism that she ended up just keeping out of habit, so that style isn't really about being "true to herself". Rather, this is a chance for her to find who she really is.
All that said, my personal rankings and evaluations are as follows:
- Cute: It's softer, but still practical and makes her seem energetic. Would be understandable if she switches in a longer skirt though.
- Sporty: It doesn't look bad, but I'm also just a sucker for practicality. It's a subdued step towards taking down her walls, but probably the closest to her comfort zone.
- Elegant: It definitely looks fantastic, but isn't suited for very active date at all. It's also leaning a bit too much into...I wanna call it a "mature adult woman" vibe? Basically it's best for dinner dates at higher-end restaurants or perhaps seat tickets to some sort of performance.
- Modern: Probably does the least for me. It covers up the most, but it's a modesty that doesn't feel very "her" for some reason. I get the feeling it's also the least practical for an active date. I guess it would be good to meet your partner's friends or family in or something.