First date (in a long time!) outfit help

[Definitelynotme2022]

I have a first date for dinner and drinks at the weekend. It's my first date in 19 years..... so more than a little daunting.

I'm 53, size 16. Any ideas? I prefer things that aren't too shapeless as I have an hourglass figure, so they tend to look like tents on me. My normal go to would be a plain jersey dress, probably in black or navy with a nice jacket.

I clearly have too much visual imagination because wearing an all leather dress or even a skirt on a first date conjures up the image of Ross on Friends trying to get out out of his first date leather trousers with talcum powder! 😂I cannot imagine anything more uncomfortable.

I like the Baukjen dress.

Do people go to softplay in dresses? Really? Surely leggings and joggers are more appropriate, especially if you kid wants you to join in.

I think you're definitely in the minority if you'd wear a full length gown to a first date.

I don’t personally like to stand out & I think lace/ leather on a first date would make me feel really self-conscious. There are some other good suggestions here. I would probably opt for a plain blouse with a pair of patterned trousers.

Some of these replies are hilarious.

Lace, leather will make you look really try hard unless you wear it in a very relaxed way like a bustier with baggy jeans - and this will only look good on a very slim 22 year old.

As for showing up in a full length gown, it's a date not a wedding anniversary party.

The dresses and jackets being work only is reminiscent of the early noughties when we were all poured into tailored dresses, sky high heels and (probably) control pants.

The bloke who came in talking about a men love a little black dress is actually bang on about men. Men (assuming you're meeting a man) like to see your figure and for you to look feminine. Fussy migraine inducing patterns, huge floaty styles get in the way of that. It's up to you how much you care what they want.

I remember my now (but not then) DP bumping into a woman and having a quick chat. He was relaxed, she wasn't. It was clear something had gone on. It transpired that they had gone on one date but he hadn't followed up. I was surprised. She was really good looking and on a shallow level way out of his league. I asked him why and he shrugged saying no chemistry and she wasn't really making any effort. It was so vague that I pressed him - I was intrigued to what constituted making an effort. He had to think about it then he said "she just didn't seem interested in me or being on the date.. " then almost as an afterthought or he threw in "she walked in wearing jeans".

I don't know why but I found this so bizarre. He had taken her not to be interested because she wore jeans. They probably cost her five times the amount I spend on one of our date dresses and I suspect she looked amazing in them but there you go.

Personally I think the many posts with some form of fitted dresses showing your waist are your best bet but not too far from what you usually wear. A bright colour will be flattering on your skin and make you look youthful. Nice chunky jewellery to show you're taking it as a night out.

I hope you have a great time. Where is the date on and how did it come about?

I am 58 and hourglass size 18.
I would wear black trousers and a v neck wrap top styled with nice jewellery I like Monica Vinader pieces, tan boots and a tan or leather jacket.

Alternatively I would wear the Joanie dress as mentioned above, I like that, (I might even order it). Maybe with boots or ankle boots.
https://joanieclothing.com/glorie-green-floral-print-wrap-dress.html

Keep it simple, smell divine and wear whatever you wear with a smile and you can get away with anything.

It’s this I can’t get past, I mean the model is 5ft 10, and it’s far too long for her, never mind picturing the op in it at 5ft 3 and a 16. And it’s 1200 quid!

https://www.phoebephilo.com/en_gb/high-slit-tailored-column-skirt-berry-wool

@Jf20 you are supposed to pay more on top of that to have the hem taken up.

I absolutely love this dress from Baukjen. Malin Cupro Dress – Baukjen And it won't be as sweaty as leather. Has shape too.

Damn, sorry, the above seems to be sold out. But there are other nice dresses on there.

I'm following OP because I have a similar dilemma. I posted before, but should have specified I am in no way adventurous or stylish.

I also like a wrap dress but can only find ones I'd wear for work. But no idea what the alternative is. Not helped by being unhappy either my weight. I think I'll have to go shopping.

Was just going to suggest jeans 😁
Mom/boyfriend jeans turned up at the ankle, barely there nude heels (or whatever footwear you find comfortable) over a long sleeved white or black bodysuit. Minimal jewellery, maybe just a simple bracelet? A nice over the shoulder clutch.
I would go casual, not too dressed up.

I love the outfit that @newyearnewknees posted. Stunning.

Wonderful outfit, but I’m not sure I’d wear that on a first date unless I was meeting a very fashion forward Architect from Berlin or something.

To be fair, I should probably add that we already know each other and he’s used to seeing me in sweaty sports kit so I figured any “normal” clothes was probably an improvement and he was wearing similar so we’d clearly got the same vibe for where we were going!

If I personally were going on a date, I would wear dark jeans and a silk shirt in a bright colour with a nice handbag/boots and my wool coat, so similar to what I usually wear, but slightly elevated.

last few first dates I went on all for drinks

• black maxi dress with doc marten boots
• mum jeans and a white shirt, white trainers
• mum jeans and a body suit, white trainers

dress for the place your going. Nothing worse than feeling over dressed if your going to a pub or bar or a restaurant where it isn’t super fancy

I am 55 a size 14 hourglass and would wear my jeans, a blouse and a short Chanel inspired jacket. I’d hope this would give a stylish and I’m happy with myself vibe.

God, I wish I have £1700 lying around to buy one skirt. 🤣

I think your silly to dress up.
Wear something you like, that has layers, so if your hot or cold to can change.
I always thing nice black trousers a white loose shirt, gold jewellery and nice make up and some colour with a jacket and scarf. Bracelets add a touch of fun, think a bit like Princess of Wales at an event.

Who are you addressing, @Bollindger? The OP hasn’t been back - so it may be premature to cast aspersions on her unknown wardrobe choices.

Which princess of wales? Because Kate certainly doesn’t dress like that, scarfs are very old fashioned. I’m not even sure Diana dressed like that.

Oh, I don’t either duck. It was a comment on the sartorial direction, rather than budget.

Yeah I know, your comment was on a link from another poster. I was more poking fun at that skirt even a suggestion. I just always find it funny when people ask for outfit suggestions and folk go posting links to 4 grand ballgowns like we're all millionaires here! 🤣

Amazing. Love this. The dark blue is currently on sale. I'm ordering.

Are they ? I wear scarves all the time....

You might like something by Karen Millen - size 16 black dresses:
https://www.karenmillen.com/womens/dresses/black-dresses?prefn1=sizeRefinement&prefv1=16