I recently traveled to Florida for 8 days without checking baggage or doing carry on. Here's how I did it. I packed:
3 black tank tops
4 pairs of underwear
1 bathing suit
1 black dress
1 black skirt
1 pair of black shorts
The clothing was rolled up tightly and packed into one side of my purse (think large purse/tote).
In the other side of my purse fit my phone, camera, minimum makeup, wallet, ect.
As I was visiting my sister and not staying in a hotel, I knew she would have other essentials like makeup remover, bathing items, skin care, ect., so those things didn't need to be packed.
I wore my favorite jeans, a dark blue v neck tee, a black v neck sweater, a wool/silk scarf, a black blazer, a pair of "no socks", and a pair of lugz white sneakers.
Jewelry was basic: My wedding rings, a couple of silver rings, stud diamond earrings, small rose gold pendant necklace, and a basic silver watch.
In hindsight, I did not need the black shorts or the black skirt, and they took up valuable room in my purse.
My purse is a large Coach bag with a detachable smaller bag inside, which was perfect for going out to dinner.
Here's some pics. Feel free to comment any additional ideas you may have on traveling light.