Search Results: clothing for a guy

So I like it that he gives me suggestions and all but a couple days ago he texted me these pictures and told me to find the outfit. It is kinda a cute outfit but I’m not sure about it.

I’m not sure whether or not it’s just a tshirt or if it’s an actual dress (I can’t find it anywhere)

Is it just a tshirt or is it a dress?

I am not going to specify what type of date. There’s not a lot of walking, mainly just sitting and relaxing. In general and in your personal opinion (guys or ladies), what clothing style would you like to see your date wear?

So I'm doing a language exchange thing with this guy. And I'm thinking he might be interested in more. I wouldn't be opposed to that either and have always quite enjoyed spending time with him. We always meet at 5 pm and he would usually want a beer or wine. Last time (our second time) I suggested we continued to grabbing a bite followed by some beer and ended up talking until almost midnight. After that he seemed to be more interested (lingering looks, texting the next morning with a more enthusiastic tone, etc).

Context: we're both older, I'm 32 and he's 40. But I'm so inexperienced in dating and have been chubby all my life, so not used to guys finding me attractive either. I'm a tight jeans and loose shirt type of woman, but I've been wearing some tops that showed a bit of skin, like tops with cutouts or the smallest bit of cleavage. But I know that the nature of the meeting is (as of now) still a friendly and casual thing, so I don't know.

What kind of clothing do you think is appropriate for this context?
** Please no unsolicited comments about weight, etc.