Bi-Dating Help - No One Else To Talk To

I’m a 34 yr old male that has been out with a friend multiple times, and last weekend, after a really nice time together Sunday morning, and a couple hours on the phone Sunday evening he confided in me what he has always wanted from his partners because it would show a commitment to him beyond just his money, success, etc… I’m invited to go away with him and a number of other couples a week from now for 4-5 days, and I really want to give him what he shared with me but it’s hard not to feel uncomfortable about it. It would be amazing to receive some input/advice from someone honest and unbiased. (preferably a female opinion)

What he’s always wanted is for his partner to wear a few different / specific styles of unisex or possibly even women’s sneakers and outfits that are definitely more feminine than what I have typically ever worn. Things like Capri style pants that only come midway between my knee and ankles, cut off Jean shorts, etc… the clothes I think are pretty flexible but the sneakers are made by Reebok and they’re called the PRINCESS and FREESTYLE. One is low top and one is more mid or high top. I was under the impression they were unisex style but the princess name doesn’t seem like they would be. I went thru all the different color combos he ranked from 1-10 and I actually found 3 of his top 5 in my size. I wear a 10 in mens and everything I’ve read says I’ll need a 12 in womens and there aren’t a ton of those out there. I just need to know that I look okay in them if I’m gonna do this, I have no idea what socks would look best with these sneakers and different pants/shorts options, basically I just want to do this but need help to make sure I get it right.

I don’t see how I can add in the images of each sneaker but I’ll keep trying to figure it out and add those in as well.

I REALLY appreciate anyone willing to give me some advice. It might require me sending pictures of different outfits and I realize that might take up too much time. I don’t want to be disrespectful or difficult in any way, and I promise to be polite and positive no matter how disappointing or difficult your feedback might be. I’m just very excited and very nervous.

Thank you so much.
Trace