First date with someone I might actually like outfit dilemma

[Lambzig]

I have been messaging someone for about a week and we are meeting for drinks and dinner tonight. I might actually like him, the texts are very sparky.

Could you please help with what I should wear?

Upmarket pub in a cotswold town.

I am having huge outfit dilemma as I ordered something new to wear to give me confidence and it hasn't turned up.

I am now torn between jeans and silk blouse and trainers. Or slightly off the shoulder black jumper, maxi skirt and Isobel marant cowboyish boots.

Open to other suggestions.

I am 5ft 3 and a size 8 and 55 if that helps.

I dont know what's wrong with me, I dont usually have this problem.

Either would well. Although I would probably go boots rather than trainers with the jeans (depending on the cut) and a nice jacket.

I wouldn't wear trainers for a dinner first date. Either outfit with the boots sounds lovely. What do you feel best in?

I would go with the 2nd option. The off the shoulder jumper flashes a little bit of skin but not in an OTT sexy way. And boots definitely over trainers for a date.

Going against the grain, I'd go for the first outfit. As long as they're nice fashion trainers, not like Skechers. Trainers and jeans are relaxed and comfortable, silk shirt is just dressy and feminine enough. A date will not go better because you wear boots over trainers, I doubt most men would even notice.

Do the boots work with the jeans or is it not the right cut?

I like the sound of the off the off the shoulder jumper and skirt.

Yes I agree, trainers doesn’t send the rights signals

Could you wear the black jumper with the jeans and boots and maybe a belt so you could slightly tuck the jumper into the jeans? What are the colours?

Where something you feel comfortable in. I don’t mean joggers obviously! But not an outfit you’re constantly having to readjust or mess with.
Whichever outfit you feel most confident (but also the one you feel most like yourself in).
Hope it goes well.

Maxi skirt and the boots, because I'm slightly obsessed by cowboy boots at the moment and so as far as I'm concerned, a man who admired them would a keeper.

That said, I very much doubt many men would even notice plus I am very shallow and my last date was in 1993.

Hope it goes well.

Outfit 2 for me.

Thank you so much, it’s good to have second opinions. I’m just setting out wearing the skirt and boots and jumper as that’s where the vote seemed to go.

I had a massive clothes faff and let my daughter decide in the end.

I’m actually petrified but i think i have to go through with it now.

I’d go for skirt option too. Any length I think it’s a bit more flirty if you wear a skirt, at least on the first date.

Perfect, good luck OP!

Hope it went well OP, comeback and update us!

How did it go?

It went very well thanks, lovely evening. He’s lots of fun and we stayed until the restaurant closed. We had a very nice kiss after he walked me back to my car.

I’m seeing him again tomorrow.

I know it didn’t really matter what I wore, but feeling good about my outfit always gives me a bit of confidence.

Exciting! So pleased it went well and good luck for date no 2

Lovely update. Enjoy tomorrow.