Capsule wardrobe for long weekend in the sun

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I have to make it fit in a small carry on bag. I say "sun" but it's October so the evenings will be cooler. I know it's early but leave it, I won't be able to buy summer clothes.

I have:

Travel in jeans, "nice" t-shirt, trainers
Long floaty sundress, blues in colour
Bikini, blue/aqua
Navy shorts
2 x strappy tops
T-shirt dress to wear as beach coverup
Underwear
PJs
Bare minimum of toiletries/makeup, I think I will have to squeeze in a hairdryer
Running kit (I'm going to run a race)

I'm stuck on a jacket/jumper and shoes.

I'm not a sandal person, I hate grit in my feet and frankly my feet are a mess from the running, so I'd usually wear the dress and shorts with trainers. However, not running shoes, white leather trainers. I obviously need to take running shoes, I can take new, clean ones, but I don't think I can manage a 2nd pair (I have big feet, which doesn't help). I could squeeze in a dainty pair of sandals/flip flops, but my feet....

And a jacket or jumper. Quite likely I'll need something to travel in at this end, something to go over the dress or with the jeans/shorts in the evenings. I'll also possibly need something for after the race. A denim jacket? Leather jacket? Hoodie? Or some sort of sweater or cardigan?

Apols for the long link, but this is a great option for a denim jacket/shirt that works over dresses or with jeans; it's described as a shirt but it's thick and I wear it as an extra layer on top of a t-shirt, dress or vest top You could wear it with a scarf if it gets chilly in the evenings.

www.marksandspencer.com/denim-collarless-puff-sleeve-shirt/p/clp60520876?intid=mobile_app_pdp_share

Agree with @Gherkingreen, a shirt or “shacket” like that is very useful, you’ll be surprised how much it goes with.
for sandals have a look at Menorcan sandals, there are a few nice brands out there and many styles cover the toes. Very comfy and pack smaller than trainers.
For makeup I use a tinted spf 50 with a highlighting concealer and a dusting of light reflecting powder as my minimalist makeup.

I think it depends how far south you are going.
if it’s southern Spain I’d travel in cotton trousers rather than jeans. I’d take a denim jacket (defo no double denim), that marks top is also too full in the back for me. I’d also usually take a thin jumper( possibly a sweatshirt as an alternative) for the plane (on me) so that’d be another evening option if required.
if you don’t want to wear sandals maybe a light pump could be squeezed in
www.marksandspencer.com/canvas-lace-up-printed-trainers/p/clp60540122#intid=carousel_FUNH_AT_RECENT_END_FIND-PLP_18_13

If its Ryanair or easyjet it doesn't cost that much to get priority boarding that includes the bigger cabin bag.

That's probably what I would do if I thought I was going to struggle with luggage, needing sports kit and what is probably varying weather.

Can I query what you will be wearing in the evenings? You mention one sundress, then a beach cover-up dress (would this be suitable for evenings too?), then I’m not sure if shorts/jeans/strappy tops would work if you’re at a nice restaurant? I suppose it all depends on your itinerary but I think you might need one more evening option?