Packable sun hat and travel purse for Jamaica?

I have a large SPF sunhat that I bought at Sam's Club last year that shades my face well but I don't think it will pack in a suitcase easily. Any recs for a cute sunhat that can fold or roll up to pack in a suitcase? Prefer if it has the UVA blocking in it. Also, I am trying to figure out a purse to take. Something that is easy to care and secure for in the airport, but can also be used if we go on an outting from our resort. I have several sling backpacks (Vera Bradley, Kavu, Baggallini), and several cross-body bags (Vera Bradley, Baggallini, Ebags, Kipling). I'd like something not too big, but big enough to carry my sunglasses case, a thin card wallet, passport, plane tickets, small cosmetic bag, tissues, hand sanitizer, bottle of water. Send me your ideas!

Hat- look at REI.

Bag- get a Baggalini tote for the plane and then have a smaller purse inside. It's how I travel. I like having my phone, kindle, headphones, charger, a layer in case the plane is cold plus the stuff you mentioned. Baggalinis are cheap if you go to TJ Maxx or Marshalls.

With regard to going on outings- if you're doing water sports, hiking, other adventures, you want pockets that zipper. Athleta skorts are my favorite bottoms. A purse makes no sense on those types of outings.

Take a cross body vs backpack.

Just got back from a hot-weather destination, and I got my sun hat from Nordstrom Rack (packed it upside down in suitcase with stuff stuffed in it to keep its shape). Got a little raffia purse for going out to dinner from Lands End (40% off + 2% beats today). I don't love the looks of Baggalini, so I didn't get one, but I'm more o.k. with the looks of Kipling bags, and they have a light gold/ metallic one, or an olive green one out now that's kind of cute if you want something that's not plain black.

I can’t tell you which hat to choose from the sun, because you need to choose from what suits you. But I can help you with finding a good travel bag. Usually, when we go on vacation I have a suitcase for my things and a small waist bag for phone, money and documents. Such as here https://fannypackz.com/m/travel-fanny-packs/ , for example. This is quite convenient, because you will have free hands and you can take with you more necessary things, but at the same time they will always be safe and at hand. It seems to me that such packs are really an irreplaceable thing in any trip.

Costco's Solar Escape hats are usually foldable. I don't know if this year's fedora version is packable, as usually they are the bigger, wider brimmed hats each year. The fedora is a great price and currently $5 off--$10.99 total and has a UPF 50 plus sun rating.

https://www.costco.com/solar-escape-...100566754.html