Coastal Comfort: October Style for Massachusetts, West Coast Ease

Hey all! I’m traveling to MA, Gloucester area mainly in October.

I am from the west coast so it’s still 90 here. I know it’ll be colder, 50-70. I’m looking for advice on outfits! Things I can incorporate more into my current wardrobe. I look good in a soft summer/autumn palette, wear mainly boho western and casual stuff. I wear things like pic 1 in summer, but don’t have much of a winter wardrobe besides sweatshirts.

Any advice on what to wear? I kinda like options like pic 2 but will it be too cold for that? Do I need a coat? 😂🫶 thanks in advance lovelies

Eta to clear up confusion

Pic 1 is what my normal style is, so I could get maybe more personalized suggestions
Pic 2 is one of my saved pins on Pinterest, just wouldn’t wear heels bc we will be walking a ton!!