From The Book of Questions by Gregory Stock.

Question #94: On a busy street you are approached apologetically by a well-dressed stranger who asks for a dollar to catch a bus and make a phone call. He says he lost his wallet. What would you do? If approached in the same way by a haggard-looking stranger claiming to be hungry and unable to find a job, what would you do?

Since buses are free in my town and most public places have a phone they'll let you use free... I'd edge away from the well-dressed stranger as being probably a con-man.
The haggard-looking stranger is invited home to a meal and we go over some of the local volunteer organizations that help folk who find themselves stuck between jobs. We have some pretty good ones locally, even if they do seem overly fond of paperwork, and there are other volunteers to help with the paperwork, especially for language difficulties or reading issues. Of course, with covid going on the meal at home is going to be backyard picnic-style, but no one should go hungry.

I've been in a situation where I needed some money to take the bus, and someone was really nice and gave me some. So I'd do it, as a sort of pay it forward thing, and because I know how hard and embarrassing it was for me to ask.

How someone is dressed or presents themself wouldn't affect my opinion, unless they are obviously drunk or high. We have a big problem with homeless drug addicts around here who harass people for money, then attack them if it wasn't the amount they wanted...

99% of the time anyone asking for food here just wants the money for drugs, which is really sad because anyone actually hungry isn't taken seriously (though we do have a lot of food banks too), but one bad event with a homeless person throwing your food on the ground, screaming sexist curses, and spitting on you really makes you never want to trust anyone again.

I personally don't give a shit if they're well dressed or not as I don't give them money.

"Sorry dude don't have my wallet"

I don't even know where it is right now lol

I would honestly feel uncomfortable, but I'd still give him money.

I'm way less likely to give the well dressed guy money. I have given panhandlers money before.

I'd give more than a dollar, as I know how much it sucks to not be able to afford something. and I'd insist on the person keeping the change. Because someone was kind to me in a similar way when I needed it at one point.