@straightorbroken I run with these:
Amazon product ASIN B07VSYLV61
They're good at staying in my ears (which I've really struggled with in the past as mine are obviously a weird shape...) And the sound quality is good.
One complaint is that the controls to put volume up and down, pause, skip is quite clunky so I tend to use it as little possible.
I also run with a armband for my phone and some shorts with just a small zip at the back for a key. I wouldn't be able to run holding lots of stuff. The clothes I wear are just cheapo stuff from Decathlon but I need new stuff really.
Lastly, for the height of winter I'd get some running gloves. Your body warms up but I was was finding my hands would go numb and it was really uncomfortable and off-putting when running. I only really needed them for December and January though. No need for expensive ones.