If you're looking for laundry tips, my advice is NOT to get a travel laundry line. They're great for some travellers, but when your wardrobe is as pared down as what you describe, the only thing you'll end up hanging is maybe one blouse and some underwear ... which you can do on a chair!
I know you're not lacking in encouragement, but I just wanted to join the choir saying that you can totally do this! I just spent 3 weeks in Asia, with temperatures ranging from 40-70F (5C-24C), and formality level going from hiking to a wedding. And yes, it was a soft-sided carry-on.
Here's the clothing I brought; sorry for the lousy picture and messy background ... I took this photo for planning purposes, never intending to post it on YLF!
Shoes: converses (that I planned to trash while hiking), plain black flats.
Accessories: gray crossbody, patterned black clutch, simple silver necklace, cream/burgundy/slate-blue scarf.
Bottoms: black baggy/boyfriend wool trousers, slim black ponte pants (with moto-styled zippers that I could hide with a long top), jeans.
Tops: Chambray shirt, t-shirt, silk blouse, lightweight/slim burgundy sweater, heavyweight camel sweater, technical gray puffy vest.
Dress: slate-blue silk shift.
Other: two heattech tops (one that I could pass as a black turtleneck if I were careful what I layered on top).
If I were to do it again, I would drop the silk blouse (I could tuck my silk shift into my pants and wear it as a top) and t-shirt (I run super cold, what was I thinking?!); basically, 3 bottoms, 4 tops, 1 dress. As you can see, having one color palette means you can mix and match everything.
Not shown are my swimsuit, hiking bag, 3 pairs of wool socks (<3 them!), black wool coat, camera, and kindle.
Warning: you might get sick of your items and not want to wear them after you return home.
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