Work night out - but I'm not working

[Actors]

I'm meeting up with an old friend for drinks tomorrow.

We worked together for 15 years or so and were really quite close (some frision if I'm honest, but neither of us ever acted on it) We used to go for drinks once a month or so, but since I left the company 18 months ago, has been much less frequent.

Anyway we're off out tomorrow. We'll be having drinks in London and he'll be straight from work, so in a suit.

I'm in a real dilemma over what to wear. A suit (which is what I have always worn before) is OTT, as I won't have been at work, but casual doesn't seem right either. My wardrobe is basically work clothes, evening wear or very casual (jeans/shorts)

So, he knows that if I'm wearing anything other than jeans, I've dressed up specially, but I don't want him to think I see this as a special night out iyswim. However, I also don't want to be too casual next to him all suited and booted. WWYD?

I know I'm overthinking and did think about putting this in relationships

Oh well, no-one cares. Can't believe this is so difficult, when I was working it was easy. I bought one really good suit per year and always looked great, IMVHO

I have a few semi casual dresses, but my legs aren't ready and opaques hopefully not necessary

Have you got a blazer?

I'd go for jeans, heels, top and blazer.

Thank you, I know what you're getting at, but my Jeans are properly casual, scruffy things you wear with Converse.

If the weather's going to be OK enough not to make white linen look ridiculous, I might be OK

Do you not want to buy anything? Maybe a pair of skinny jeans so you could do what dew suggested?
Or if I'm wearing a semi casual dress I wear coloured tights that aren't super thick but cover up my legs!
Or suit trousers with a top?

I haven't got time to shop now, but no I didn't really want to buy anything because I refuse to acknowledge that this is anything more than a very casual drink with a friend. I want to look OK, but I don't want him to think I've made any special effort

It's long and complicated. We are very much definitely just friends, but over the 15 years there were "moments". This is the first time we've been alone since I left the job and I really don't want to send any mixed messages.

Honestly....don't go.

Unless you are going to make the effort, make some moves, honestly what is the point?

How will he know you have bought a new pair of jeans specially? Does he have an itemised list of your whole wardrobe?

The weather forecast is hot and sunny tomorrow isn't it? Wear something nice and tell him you are fresh from a hot lunch date

Sorry, I'm obviously being thick, but I don't understand. He's a good friend I see quite a lot of, but usually with our DC in tow. We always have a good laugh when we go out together, that's why I'm going. Isn't that why you usually have a drink with a friend?

I don't want to go out on the town in London looking a mess, but I have no desire at all to make myself attractive to him. We're both happily married (for more than 20 years each)

Thank you DewDrop. I've got it now. My main confusion is that for casual drinks I usually wear jeans and converse, except when it was after work drinks in London, when it would be much more formal, as straight from work.

Scruffy doesn't seem right as he'll be smart and so will everyone else in the pub (but not at my local)

Summer frock it is and keep my legs under the table!

Why not get your legs ready.. bit of Sally Hansen and off you go

Now, at Christmas I bought Sally Hansen when I couldn't decide what tights to wear with my frock

I'm very pale, so I bought the light one, but even so, I decided it made me look ridiculously orange and washed it off. Today I dragged it out from the back of the cupboard and now I don't think it makes enough difference....