It totally depends on where you’re going! I wouldn’t wear a dress in winter for happy hour or drinks but I would in the spring or summer.

As a 41 year old who was recently on the dating market, I would suggest jeans and and a sweater that flatters your figure. V neck is a safe bet. Wear some fun earrings and leave the rest of your jewelery toned down. Heels if you like wearing them, but boots or flats are fine!

Have fun!!

Wear a pair of pants that compliment your legs with a sweater. Something you’re comfortable wearing. You can always wear lingerie under if it helps your self confidence to make you feel alluring.

Definitely depends on venue. I would do as suggested above:
Black wrap dress, knee length, if you have a good figure and good legs.

Black turtleneck with black pants or black jeans and boots. Long gold necklace and simple gold earrings.

Depends on the venue- fancy restaurant? Black pants - nice camisole with a cropped blazer and heels

Casual place- your cashmere v neck and jeans

I would think about wearing what will make you feel fabulous about yourself, and also is super comfortable. A favorite sweater or blouse in your favorite color paired with neutral slacks. A knit sweater dress with a favorite pair of earrings. I feel like black is kinda worn out. I like browns and navy, but pick your favorite!

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

Depends on the dress and your personality. I would do a black wool wrap dress and wear it confidently. That’s much sexier than a large this or small that.

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.

This!!

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!

I'm close to your age and this is about what I wear. Good luck, OP!

Where are the dates?

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

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!

Where do you usually go on the dates?

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.

Small chest is not bad. You won’t look matronly.

I'm back on the dating scene post-divorce this month with two great prospects. What the heck is age-appropriate sexy for my age? Would love to nail a classy, sexy look vs dowdy or too young for my age.

I've got a pretty decent (fit-ish) frame 5'9", size 4-6, though I'm small chested. Need the savvy of this forum to help me out!