I just spent 4 weeks over seas with just carry on..... I do it because I prefer to travel by train and foot, and often go to out of the way places, where a lot of baggage is a serious burden.
The wardrobe I took was relatively casual, easy to move in, but still nice enough to go out in. It was cold where we went, so I took a lot of wool and cashmere which packs well. I took thick wool tights, skirts and wore a pair of Keens that had a very good walking sole, but a fancy enough upper to look fine dressed nicer. I found a packing method online that allowed me to pack 8 sweaters (4 turtle necks and 4 cardigans) 2 base layers, 4 skirts, 4 pairs of tights, a pair of insulated tights, and all my undergear in one carry-on. My outerwear stayed on me - waterproof/windproof jacket, gloves, scarf hat. I was able to do laundry several times during the 4 weeks and thanks to the wonders of the fruit of the sheep was not smelly.
My shoulder bag was stuffed full of my camera gear (and I'm a pro, so it wasn't a little point and shoot...) and Ipad.
Years ago my husband and I did a bike tour in the south of Spain with very, very little - it was a self arranged tour so anything we took we had to carry. It was warmer at that time of the year. We took two sets of biking gear - one to wear one to wash, biking outerwear, one set of town clothing and sandals to wear off the bike. I ended up buying a light casual jacket because I was a little cold one evening, that I still have and still wear sometimes.
worn out sandals at a Buddhist shrine - offerings from pilgrimagers




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