Help dress a middle-aged fatty for a date-type scenario

[EoinMcLovesCakeJumper]

That's it, really... to be clear, I haven't secured any dates yet, but I am about to start putting a profile up on some OLD sites, and I would feel less nervous about it if I had my date strategies sorted out in advance. I'm an overplanner, I just try to work with it these days!

So I am 40 and plus-sized. I don't have much body confidence and there's little I actively like about the way I look, but I suppose I'm at peace with the fact that this is how I am and I generally try to dress to cover up, but in a stylish way. I wear mostly slim-fitting trousers and midi skirts with brogues or long boots, which is fine for work and leisure time, but I can see how it wouldn't be the most appealing thing to turn up to a date in.

I am 5'5", pear-shaped with a belly, no waist to speak of, proportionally small boobs. I can't wear heels because of joint problems, although block-heeled boots are ok so long as I don't have to walk very far in them.

Any and all ideas are welcome - for lunchtime coffee dates and perhaps evening drinks. I do follow trends but often find they don't really suit me, and it's been so long since I dated that I don't really know how formal or dressed up you're expected to be these days.

I think a lovely pleated midi skirt would look nice and a slimmer top tucked in- have a look at Louise Pentland on You Tube or Instagram- she is your shape and she looks great.

From what I read here dressing up for a first date - casual coffee in you lunch hour, or second date - walking your dogs in the park on a Sunday morning, would be an extreme faux pas!

crochetmonkey74 do you think so? I'm not sure... she has much bigger boobs than I do, and I don't think the pleats actually do her many favours. I've always avoided adding extra material to my widest points, anyway. But I admit I'm out of step with the currently fashionable silhouettes, so maybe I could do to be more open-minded.

SurpriseSparDay sounds like I really am out of touch, then. I wouldn't be looking to turn up for a coffee date in a floor length ballgown or anything like that, but I would want to look like I'd made at least some effort. How much do people think is too much?

Danielle Vanier on Instagram is another one to look at. She always recommend's affordable clothes and I think she looks great. She's put together a black polo neck with a red zebra print midi skirt from Matalan - perfect date outfit in my opinion.

Annnnd she was promoting the dating app bumble in her stories yesterday - I didn't pay too much attention because I'm not currently dating.

Speaking from a position of extreme ignorance on the topic of dating ... I honestly think you should dress and present yourself as if getting dressed is a normal everyday thing.

Presumably you’ve joined OLD sites because you want to meet someone? Well that could happen anywhere, at any time. So why not merge your ‘profile’ self with your actual self? If you feel you’re generally stylish and well presented - nothing more should be required.

I try to be as well-turned-out as I think I can be, but I don't think that's necessarily the same thing as looking nice, if you see what I mean. I think I look perfectly smart and professional when I dress for work, but it's not the image I want to project if I'm meeting a potential romantic partner. I'm not saying I want to turn up in a vampy dress with my chest hanging out, mind, just some sort of happy midway point between the two sort of thing.

Shirt dress? Goes up to a size 20. Looks dressier unbuttoned.

(Don’t think you’ve mentioned exact size or budget?)

That's nice, and I have some boots like the model's that would go with it. A bit out of my price range (probably more like £50 tbh) but I'm sure there are similar things available for less. I'll have a look around.

I'm a big size 16 but I think I look bigger. I look at the "plus size what are you wearing" thread and see women on there who say they're a size 18 or bigger, and to my eyes they all look far slimmer than I do. I think it's because I don't have nice legs and my heavy thighs are difficult to dress. A midi skirt or dress would do the trick though, so I will concentrate my efforts there.

Ah! Now we’re getting somewhere.

And 16 (even a ‘big’ 16) is nowhere near plus size!

While I’m on the same site I’ll suggest these which would look great with a big roll neck or deep v neck cashmere jumper for a faux-casual pub date over the next few months. Again, you could as you said find a cheaper equivalent.

(One more thing if you’ll forgive me - it may be that you’re planning to shop second hand from wherever - but if you’re planning to buy new things £50 won’t perhaps buy the sort of stylish dress that would do you justice. If you really can’t afford more there’s nothing more to be said. But if there’s any elasticity in your budget now might be a good moment to upgrade. Particularly if your planning on going on lots of dates!)

Putting aside the numbers, I am definitely fat, but I suppose I said plus size because it's less loaded than fat. I don't mind for myself but I know others do.

Things are tight, unfortunately. I do look in charity shops regularly and I am sometimes lucky to find a quality item for peanuts. Invariably when I'm looking for a specific thing you can guarantee that nobody will have donated one within a 50 mile radius of me. I'll look, but I do know it's harder to look put-together in cheap clothing.

Harder but not impossible! If you’re near a TK Maxx it’s worth investigating regularly. They often have far higher quality stock than surrounding High St shops - your £50 may get you something ‘worth’ ten times that.

Varieties of texture add style to an outfit. And natural fabrics. And simple shapes. In fact, do you ever browse the racks of men’s clothes in charity shops? If you can find a plain white collarless shirt in heavy cotton that could be dressed up for day or night. Or a v neck cardigan. (I used to buy half my wardrobe from vintage clothing markets and the men’s clothes were always the best.) And oversized, androgynous dressing is very fashionable at the moment.

Honestly I think baggy androgynous might be fashionable but I wouldn't wear it for a date until they've got to know you.

I'd play it safer eg a wrap or scoop neck slightly a-line dress just above the knee in a colour that suits your skin/hair/eyes. Nice boots. With a smart/cool/casual jacket depending on your style. Show a bit of skin eg neckline as above, shorter skirt if got good legs or bracelet length sleeves. The old trinny and Susannah type advice.

Get a new bra to make you feel nice on the inside

Also if you do want to wear a dress Roman originals are good value

Eg
www.romanoriginals.co.uk/blue-pocket-detail-dress-14012409

Wrap dress?

Get yourself a good balcony bra which will even out your proportions and make the most of what you have.

I'd go for some straight-legged dark jeans, smart boots with a medium block heel - maybe in a coloured velvet or suede so they don't look too mumsy, and then layered tops in rich plain colours - maybe a longline silk camisole with a very long, fine knit sheeny cardigan over the top, or a long velvet jacket.

I usually wear Doc Martens and cocoon shaped everything 8n my day to day life. But for a date I wear heels that I can walk in, at the moment heeled boots, skinny jeans/dress (usually short)/short skirt/ fitted polo neck or silky shirt, do my hair and definitely wear make up. I don't agree that you should go as your every day self for a date, unless of course your day to day look is smartish and slightly sexy, mine definitely isn't.

Also dorothy Perkins in your budget
Eg
www.dorothyperkins.com/en/dpuk/product/dresses-5699972/womens-dresses-5686813/black-flute-wrap-dress-9236884

Or
www.dorothyperkins.com/en/dpuk/product/dresses-5699972/skater-dresses-4888369/black-printed-dobby-chiffon-fit-and-flare-dress-9294691

Lots to look at, thank you. No, I don't have good legs. My general style is to wear long boots with a midi dress or skirt so that there isn't any leg showing. I like some of those dresses but think they'd be too short. I have a long line silk vest and a kimono top that I could wear with jeans and boots though - that might work.

With the best will in the world, I think you would have to be a lot more generally attractive than me to be able to wear baggy second hand men's clothes on a date and not instantly repel the poor guy. I would look like a bag lady!

In truth I was only considering the white shirt for date wear - the rest was just me getting carried away!

(Also I would look many galaxies beyond ridiculous in a wrap dress!)

I second the shirt dress, but look for ones with vine in the skirt. The boden isodora is roomy and on sale for £65 and goes to 18. I'm a very hippy 14 and there's plenty of comfort and room in the 14.

Something like this that could be dressed up or down a bit?

Yes, somehow wrap dresses just don't work on me. I don't know why, I like them in principle, they just look like dressing gowns.

I like the cord one and the one from Boden. I am into colour as a rule, does the Monsoon dress come in any?