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Unless a date was specifying where you were going and leave it up to you to decide what works best ( cafe vs movie theatre vs picnic vs bowling ) I’d have run a Mile if any dates told me what I should wear.
Well, if you are looking for ideas, a nice look for a date is a hot pink skirt with a button up white shirt and a Navy blue v neck sweater on top. You could add pink stockings to cover the legs if it’s cold outside too .
This would not be suitable for a woman in her 40s.
I would wear whatever makes me think "I look cute" on a date.
Some ladies look super duper cute in a happy little sun dress, and flats, and they're totally comfortable in something like that. Others will feel more comfortable in jeans, and a nice top, and it's totally up to the individual on what constitutes a nice top.
This would not be suitable for a woman in her 40s.
Why not ? A button up shirt and skirt with a sweater on top is quite common among 40 year old women. They also add some sort of tights to warm the legs if it’s cold out.
Unless a date was specifying where you were going and leave it up to you to decide what works best ( cafe vs movie theatre vs picnic vs bowling ) I’d have run a Mile if any dates told me what I should wear.
I did this exact thing on a 3rd/4th date. I told her to "wear black jeans/denim, and a fitted leather jacket." She wasn't too happy with this, until I pulled up to her place on my RoadKing Harley. We went on the Tijuana Toy run, along with 6000 of my close, personal friends. I had a backpack FULL of candy, and as we rode in the parade thru the colonias of TJ, she threw the candy out at the kids lining up along the streets. She had a great time. All the bikes closed Avenida Revolution, in downtown TJ. Yeah, we had some fun. I had lots of stuffed animals to hand out to the kids. Luckily, my date spoke Spanish, so she could make sure the toys went to little kids and not some older person that would steal it from the kid and then try to sell it back to some tourista.
Anyway, this was before we needed passports to go "back and forth" to Mexico. It's all different, now.
I did this exact thing on a 3rd/4th date. I told her to "wear black jeans/denim, and a fitted leather jacket." She wasn't too happy with this, until I pulled up to her place on my RoadKing Harley. We went on the Tijuana Toy run, along with 6000 of my close, personal friends. I had a backpack FULL of candy, and as we rode in the parade thru the colonias of TJ, she threw the candy out at the kids lining up along the streets. She had a great time. All the bikes closed Avenida Revolution, in downtown TJ. Yeah, we had some fun. I had lots of stuffed animals to hand out to the kids. Luckily, my date spoke Spanish, so she could make sure the toys went to little kids and not some older person that would steal it from the kid and then try to sell it back to some tourista.
Anyway, this was before we needed passports to go "back and forth" to Mexico. It's all different, now.
Notice the tailoring. Notice how, although it does show your curves, it's also modest at the same time, without being frumpy. And it can be worn untucked, if you want to hide the mom-jeans high waist. You can roll the sleeves up to 3/4-length, for a more casual look. If you feel it's too curvy for a 1st date, you can wear a sweater over it.
Love that white shirt - it's exactly what I've been looking for to add to my wardrobe. Now, hopefully it comes in a petite size. What is the name of the company? The link only shows a picture on my computer.
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I had lots of stuffed animals to hand out to the kids. Luckily, my date spoke Spanish, so she could make sure the toys went to little kids and not some older person that would steal it from the kid and then try to sell it back to some tourista. 
