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.

Pretty much yes. Sorry..

Well, that's pretty creepy.

S&B is INSANE

As you can see OP, we need guidance on income, location, likely venues.
Else the suitable outfit suggestions will range from fistfight in dodgy bar after bowling and burgers to exclusive avant-garde dining experience with optional high-speed getaway.

I had a guest date on Saturday night, I’m 52. I wore black cuffed utility trouser, black satin blouse and blazer. Don’t go spending a fortune as he might not make the cut 🤣 Sorry in agreement first 2 dresses are far too formal and very expensive

To be fair, OP says she's 53 not 5'3 - but yes, if the guy was an international architect and our date was at Noma, this might be my choice. A glass of Pinot on the high street, not so much. I'd go the non-showstopping route, he'll only see your top half anyway. Washed hair, a favourite necklace and lippie will do most of the work. Smile and relax will do the rest. Hope it goes well!

I tend to go jeans and blazer for first date. Or fitted knee length dress with black tights and ankle boots. Coat same length as dress.

Yes but it’s hilarious to see what people suggest ! 🤣🤣🤣🤣 I always want to post please don not wear this

It helps that they know you, because they already know how you dress, and that certainly hasn't put them off, so wearing something you have already that you like and feel comfortable in is probably good advice. It is hard to give further advice, if you want to try something new, since we don't know your height, colouring or preferred hair style. I tend to avoid high heels, unless I'm certain no difficult walking or standing is involved, & these days, they are a bit eventy, unless espadrilles or wedges, so best avoided. A stylish kitten heel is OK though, if you want to be a bit dressy, with some cullottes or cut off wide leg trousers with a T/ shirt/ blouse plus short jacket/quality cardi, or you could wear some quality loafers or flat espadrilles. However, shoes for an evening out mustn't look cheap if you are going for a dressy look. If its cold and wet & you like Jersey dresses, I picked up a wonderful deep bluish green merino cashmere mix one in the sale in House of Bruar. I wear this with a soft tie black flexible leather belt, a simple lightweight long black mac & some black Blundstone Jodphur boots...they are seemingly indestructable and very waterproof. I've checked, & this dress has been snapped up, but they are worth a look generally. Before you do anything, update yourself by googling fashion for over 50's and have a good rummage, which will eventually lead you to pinterest where you can get a lot of inspiration. Look at what you already have in your wardrobe and see if it ties in with any looks that you see that you like. Then go off and fill in the gaps. Boden on their website have a huge gallery of photos sent in by customers weaing their clothes which is quite interesting too.

Before you do anything, update yourself by googling fashion for over 50's

The OP has abandoned her thread, but I feel bound to speak up for the legions of stylish women over 50 who may, like me, have been reading Vogue since their early teens and imbibing evolving fashion more recently through the websites and shops of say Margiela, Rick Owens, Celine, Phoebe Philo, Gabriela Hearst, The Row, etc, etc … Whether we can afford the clothes new or pre-owned, or not. I will not be following your advice, @Oldie2 - nothing could be further from my own world, and I don’t know any woman of my age who wouldn’t be too busy roaring with laughter to bother to feel insulted by it.

The only situation where I might I be wearing a House of Bruar dress and Blundstone boots while out for dinner with a date would be if we were on safari - hence the boots - and I were forced into the dress by kidnappers …

@BlossomBlossomBlossom you came onto a thread started by a size 16 woman in her 50s who is going on a first date and already feeling nervous and advised her to wear this monstrosity
https://teurnstudios.com/products/maxi-leather-dress-powder-pink?_pos=13&_sid=de4162262&_ss=r

You're really not in a position to be laughing at anyone's advice.

well I've been reading Vogue since I was a teenager,, and love that Phoebe Philo outfit. But I wouldn't wear it on a first date. I wouldn't wear any of the dresses linked to on this thread either.

OP, I am 53 and have lots of first dates! I wear either black jeans (straight) and an equipment silk shirt and ankle boots. I know I look good in the jeans and the shirt is undone so it's quite low. Or I have a shorter dress from Zadig & Voltaire that I wear. But I wear that on date 2 not date 1.

I agree with the poster that says wear something you're comfortable in.

I'm assuming her date isn't at Noma. I'd wear something very different to go to Noma (in fact I did once have a date at Noma and wore a very lovely dress and heels).

No, @Ohnodontwantthiscrush, if you read with more care you will see that I made a preliminary, general suggestion of a blue silk dress that might be flattering on the OP. (As she didn’t specify her height I chose something that could easily be altered to fit.) I then continued in a second post by musing on what I (or someone with similar tastes) might wear in the same situation. I am admittedly rather older than the OP, and accustomed to enjoying what I wear.

I am one anonymous person on the Internet. It obviously doesn’t matter to me whether you like the things I would pick to wear on a date if money were no object. I happen to like the pink leather dress, (very much, I love the brand as a whole) and am currently considering another black leather maxi skirt on a different site - you are entirely free not to buy any of them. Just as I won’t be buying a House of Bruar dress.

This is after all a Style & Beauty board open to everyone - we are not all bound to like the same things.

🤷🏽‍♀️

For god's sake, OP, come back, even if only to tell us that you are going to Wetherspoon's.😂

That sounds really nice! Go for it! 👍😊

God it's awful isn't it? Imagine spending all that money to look like a shapeless sofa!

I’m really curious to know, @Illpickthatup, exactly what you would do if you passed a woman in a restaurant wearing the pink dress.

Would you race out and find some excrement to throw on her?

Or encourage the other diners to attack and laugh at her?

Or would you just walk on, maybe thinking I don’t like that dress much? Leaving her to enjoy her dinner.

Why are you so frightened by the mere existence of an item of clothing you will probably never encounter outside this thread?

Are you ok love?

All is said was I thought the dress looked awful. Why would that escalate to me throwing things at her? I'm not frightened by it I just think it's ugly. Do you often throw things at people wearing outfits you don't like? What a bizarre question.

this thread 😆. That pink dress 😬.

i thought I saw OP come back on and say her date is used to seeing her in sports clothes.

so, unless you are intending on flying and dining in Milan for the evening then I’d stick to nice jeans, boots and a blouse with tailored jacket or a dress like @Ohnodontwantthiscrush describes to flatter your lovely figure, with either trainers or flats or boots.

I definitely don’t think all 50 something women should be wearing sensible shoes & only shopping from M&S/ John Lewis but I think it’s a bit of a leap to expect your average poster to be looking for directional designer outfits as a first port of call when going on a first date.

This thread is wild. OP, I am not in the market for dates other than with my DP who sees me most nights knocking around in joggers and a hoody, but if I was I would be thinking about:

Jumpsuit/boiler suit - I have a plisse jumpsuit from ASOS and a denim boiler suit from Oliver Bonas, both of which would work for me

Midi dress - it’s so cold here still I would be looking at something I could wear with opaque tights

Jeans and something on top. I went for a fancy lunch the other day in blue baggy Levi’s and a Cos cardi, big gold hoop earrings and chunky chain

These ideas are very far from some of pps suggestions, but maybe a bit more wearable

Personally, I would go in what I would normally wear if I was going out for drinks/dinner with a friend. For me that would be jeans, smart top and boots.

I think you need to wear what you're comfortable in, so the dress/blazer that you mentioned right at the beginning. It doesn't mean you're not making an effort!

I'd probably haul out something I already have in the wardrobe and haven't worn in ages from my ancient workwear stash that's too smart for dog walking, and play with tops. I have, for example, an old silk suit that I will probably never wear again as a suit, as I bought it to meet Swiss bankers. But the trousers are great, so those, plus a slightly fancy T shirt/top and pretty shoes. Fine for anything between cocktails, winebar, gastropub or Michelin stars. Possibly OTT for Spoons.

😁😆 I was thinking the same re the outfit links and pics lol.

I mean I am not good with that kind of thing.
Some of what I've had I'm like 🤔 would you call it dates lol.

I mean I met for coffee and was cas week day usual.
The guy turned up looking like *hit 🤣🤣 which made me feel more relaxed. But still those types of me will look at the slim sexy dressed women in nice clothes.
But they don't think hold on 🤔 how do i look 🫣😆

Everyone has a different idea of casual but still looking nice.
I live in trainers/pumps so I have a black pair that are kept nice, because that's what I have to wear due to health problems.

A nice top and bottoms with shoes is nice; hair and face presentable.
Jewellery if you wear it.