I like lightweight wrap dresses in a slightly below-the-knee length. They pack easily and look great for work, shopping, or going out.
You can also very the look pretty easily by changing shoes, throwing on a sweater, etc.
I used to have like 10 wrap dresses, in all kinds of colors, but I stupidly gave most of them away when I left the US. At least I had the presence of mind to keep the black one (which is made out of some kind of polyester, so it washes easily and dries fast ^), which goes with me everywhere.
If I were the OP and committed to traveling for 5 weeks with a carry-on, this is what I'd pack:
- 1 Black dress
- 2 Black skirts (short and knee-length)
- 2-3 Blouses (in very different colors, like red, white, and turquoise)
- 2 Sweaters/ Twin-sets (in basic colors, like black and white)
- 1 Hoodie
- 1 Pashmina (in a neutral-y color, like silvery-grey)
- 1 pair of jeans
- 1 pair of cargo pants
- 2 pairs of gym/ yoga pants (nice enough that I could wear them in public, not so nice that I would feel guilty about sleeping in them)
- 3-4 T-shirts (long- and short-sleeve, in colors that go with the jeans, cargo pants, and gym/ yoga pants)
- Trainers, black heels and black flats
Well, I'd pack most of this and wear some of it (i.e., the bigger stuff, like the hoodie and trainers) on the plane.