I have not been in the dating scene in quite some time. However I would base what you wear on a few factors. What you are doing initially when hanging out, where you may be going, meeting his friends or family, time of day, temp, season, festivity and so on. Don't go crazy with getting super fancy. Something casual, a bit flashy that is just enough to keep catching his eye, don't dress to the nines otherwise you will leave no interest with him to wonder how well you can really get dressed up for a more formal occasion. Not to heavy on make up. Just some accenting. Jewelry again not to heavy. Nice ear rings, necklace and rings that are not going to take away from you. Dress cute. No sweatshirts or t shirts. A nice fitting snug but not tight top. With color. Maybe a little bit fancier jeans. Tight pants are ok as long as they fit you well and not to to tight. You want to leave some for his imagination. You want him to want to see you more and his desire to see you more dressed every time. Hope this helps.
Well where are you guys hanging out? Younger guys like me are attracted to chicks with short shorts. If you guys are going to a nice restaurant or if it gets really cold, wear something fashionable.
Almost 50... I'm not sure what you usually wear, but something like this: https://encrypted-tbn0. gstatic. com/images? q=tbn:ANd9GcTVch2xgiSRMqO_1hwsjfBnu7Cyivc1jcZBBfzyAb_9CUaOUFAq would be cute.
Make sure that you're warm, but not too hot, and comfortable. Don't go bare legged just in case you get cold (because chill bumps on legs aren't really that attractive). Skinny jeans and a tee with a colorful cardigan is always a cute pairing.
Another cute outfit where you try (but not too hard) would be leggings with a short sleeved dress. You could go with a pop of color in the tights/leggings and then a neutral-toned dress, or vice-versa.
You could also wear regular pants with a 3/4 length shirt (like a henley) and a floral-patterned scarf.
Just some ideas :) (I personally would go with the skinny jeans and tee, but you're probably classier than me!)
id say as long as u wear jeans and a cute top u should be fine and flats? no heels, no dresses and no all sequined tops. other than that i think u should be fine i hope it goes well!!
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