Anonymous wrote:I am completely clueless but for a casual look I think I would try a black v neck cashmere sweater with flare or boot cut jeans in a dark wash. And probably black boots with a stacked heel and almond or pointed toe. I would also wear some of my nicest jewelry but I wouldn't pile it all on.

But like I said, I am clueless!

Yep, this is all good.

Great advice, thank you! Especially to not waste time texting and set up several dates in a row.

So here we go! I've got 4 set up in the next two weeks. I'm kind of excited, several of them I really enjoyed the conversation just in initial texting. All are for drinks, not dinner. First one is tomorrow.

I realized looking at my closet I have lots of dressier, work clothes and nice fitting casual, but need some sexier options.

What's my style? Not fussy. At 5'9", blond and having been jokingly called a valkyrie more than once in my life, I am definitely more comfortable with a sophisticated, sexy look than sweetly feminine. I do a lot of sleek pants and tops, or a long skirt with a tighter top. I do like an A line or wrap dress.

Here are the locations:
- #1- French restaurant/bar. Comfortably upscale. I'm wearing a silk, deep teal top and black fitted, straight leg pants and suede boots.
- #2 Trendy Thai restaurant/bar (this one may get bumped for snow)
- #3 Steak place
- #4 TBD

I would love any links you have to go-to favorites of yours, thank you!

Anonymous wrote:Wear a great outfit but DO NOT put pressure on two dates. You need to set up like 25 convenient first dates in a constant assembly line so they are all low risk and low investment. Don’t get to know them at all online, just do a coffee or a drink somewhere convenient.

I agree with this advice. First meetings- keep it short, in a coffee store, no fancy, long dinners on a first date. Just look nice and put together.

OP—dress in a way that emphasizes your positive body parts.

Don’t wear a dress that’s like a lumpy potato sack. Simple, fitted, feminine.

Style your hair (ideally down) and wear some makeup.

If you share your body type and date location, we can give more specific suggestions.

Anonymous wrote:Of the responses, I wonder how many were from women and how many from men. Most men - and I'm one - will not put much weight on your outfit. Sure, we'd notice if you're wearing an old t-shirt or a ball gown, but most stuff in-between that looks pretty much the same to us.

Guy here and I disagree. I’ll notice.

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:Being feminine doesn't mean you are a trad wife. The fact that you immediately jump to extreme stereotypes tells me that you do not understand what a typical man is looking for on a first date.

At some 47, OP, I hope, is considering what she wants in a man, is looking for a man who likes her as-is, and is not trying to dress to please a stranger.

Make your own thread. OP is asking for advice.

She didn’t say she’s looking for advice on what a typical man is looking for. She asked for what might look good on her. There is a difference.

Anonymous wrote:Of the responses, I wonder how many were from women and how many from men. Most men - and I'm one - will not put much weight on your outfit. Sure, we'd notice if you're wearing an old t-shirt or a ball gown, but most stuff in-between that looks pretty much the same to us.

C’mon, you’d notice red leather and a whip.

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:Hmm that's a good point about the jewelry. So a dress feels overdone?

It’s cold. I would go business casual with a button undone depending on where you are headed.

Choose which button based on where you are headed?

Adjust which button during the date?

Yeah

Anonymous wrote:

Anonymous wrote:Being feminine doesn't mean you are a trad wife. The fact that you immediately jump to extreme stereotypes tells me that you do not understand what a typical man is looking for on a first date.

At some 47, OP, I hope, is considering what she wants in a man, is looking for a man who likes her as-is, and is not trying to dress to please a stranger.

Make your own thread. OP is asking for advice.

Anonymous wrote:

Anonymous wrote:Hmm that's a good point about the jewelry. So a dress feels overdone?

It’s cold. I would go business casual with a button undone depending on where you are headed.

Choose which button based on where you are headed?

Adjust which button during the date?

Of the responses, I wonder how many were from women and how many from men. Most men - and I'm one - will not put much weight on your outfit. Sure, we'd notice if you're wearing an old t-shirt or a ball gown, but most stuff in-between that looks pretty much the same to us.