I just finished a 14 day trip to 3 climates with a carry on roller and a laptop bag.

I had

3 pair of jeans in different colors
1 rain jacket
5 tops in various weights
1 "fleece"
medications
laptop
camera
1 fancy black long velour skirt and one black velour jacket ( I had a wedding to go to in there also )
1 pair of walking shoes
5 pairs of socks
10 pairs of undies
IMPORTANT - little packets of woolite
1 hairbrush
mascara and blush
pair of nice boots

Forget all the fancy stuff - this is to be fun. If you need to look the way you look when you go to work every day - this is probably not for you