What to wear on this date?

[caulkheaded]

Background: We’ve known each other a few years and have some mutual friends. Previous dates have been brunch/walk/pub/golf/bike ride/dinner

We’ve been together a month and have agreed we want to meet each other’s friends. For both of us there are some mutual friends.
Tomorrow it’s one of the mutual friends birthdays, but it’s someone who is much closer to him than me. There will be others of our friends there who I’ve never met before.

We’re going for brunch then a 7 mile walk. It’s likely to be quite muddy. His friends are more active than him and me, although I can hold my own.

I’m thinking of wearing T-shirt/sweatshirt/running tights/trainers then taking walking boots for the walk. Other option is jeans (better for the brunch and more flattering but less good for the walk).

What would you wear? I’m never really self conscious about what I wear but I’m now overthinking it all.

Either sounds good but I would go with the jeans option.

Jeans and a nice jumper/sweatshirt and whatever footwear you feel good in, and then walking boots and decent jacket and hat in the car to put on to set off on the walk.

Great. I wondered about wearing jeans but taking something else to change into in the toilets if I needed to maybe?

I’d wear jeans if the weather’s dry, but maybe something a bit more ‘outdoorsy’ if the rest of the group are serious hiker types or if rain’s forecast.

How about some thick leggings with flat or heeled boots then waking boots for the walk? I got some from Next which are kind of like jodhpurs(?) so can be dressed up nicely but I also wear them with trainers etc.

I’ve only got sports leggings. Leaving tomorrow about 10 so I think it’s too tight time-wise.

What sort of jeans are they? Skinny jeans would be best so they don’t trail in the mud etc.

I'd also wear some skinny jeans. Running tights can be quite revealing and I'd maybe feel a bit uncomfortable going out for lunch in them , particularly if everyone else is in jeans.

If it's a social walk I'd wear jeans. Running tights sounds a bit too sporty for what will be a friendly ramble.

I’d go for the running tights, with a spare pair in case you get too muddy.

Oh, and best knickers, just in case .

I know that they are all really sporty (ie competing for England in their teens). But we’re not near any hills so I think it’ll be a bridle way type walk. I think I’m going to wear jeans to the brunch and take something else to change into if needed.

I think jeans will run your legs! Take leggings or wear leggings. You don't want to get rubs or blisters from trousers.

*rub

If this wasn’t a date or a meeting the friends time I would wear leggings. But something just feels different because of that. Sigh.