Describing Jess' core wardrobe (and add-ons) is more difficult than it is for mine. This is both because she has more clothes and because she is overall less brand and function obsessed than I am. I believe the below is a good cross-section of what Jess has reliably had in her bag and worn since we started the trip. There are always add-ons for colder or warmer weather, for backpacking or cruise ships. In her case, those additional rotating selections have more variety and can at times make up the majority of what she's carrying.
Most travelers fall into one of two camps: people who think carrying a pair of thick, non-breathable, slow drying, bulky cotton pants with them is a total waste and those who wouldn't travel without them. Jess falls into the latter category. And though I don't wish I'd brought jeans for the year, there are definitely times when I am extremely jealous of seeing her slide on a pair of well cut, soft and comfy jeans.
Pro Tip: Your weight may fluctuate on a long trip (like if, for instance, you spend six weeks in Italy) so you may want to invest in jeans with some wiggle room or stretch.
We both have one of these and its good to think about this as more than just a rain coat. Half the time it's just as important as a wind-proof, insulation layer. We've worn this in the rain in South Africa, but also on freezing cold trains in Singapore and overnight buses in Bolivia. The Torrentshell is not as breathable as Gore-Tex, but its much lighter and thinner and the price is right.
Jess has been surprised by how well and how long these shorts have lasted despite frequent use. These shorts have actual pockets, a surprisingly rare feature in women's shorts. These are really comfortable and go with everything else she has.
Thank you Target! The cotton in this shirt is fairly thin which has made it useful and comfortable in a variety of temperatures and humidity levels. It's been washed so many times that its like wearing pajamas all day. Pretty good for a sub $10 purchase at Target.
This stretch skirt is all synthetic: rayon, polyster and spandex. It works for formal or casual and washes and dries easily. We've both found that being able to dress up a little bit is a big deal for feeling comfortable in nicer places and for forgetting, at least momentarily, that you wash all your clothes in a sink and cut your own hair.
Jess always has 1-3 of these simple cotton tanks floating around in her bag. Dark colors are preferred and they get replaced as they stretch out or wear out. Combined with her Bliss wrap and a skirt, she can dress it up. With shorts and her Tevas she's ready for a day of sweating out at Rome's top sites.
Often referred to as: "My favorite thing in my bag," Jess's kikoy is used constantly for a wide variety of purposes. Essentially a woven - and therefore softer and more durable - sarong, the kikoy's uses are many: shawl, blanket, pillow, wrap, cover-up, bath towel, beach blanket and scarf. We both have one of these, and neither of us would ever travel without it.
Cheap sunglasses can be hit or miss. After being out-negotiated by a 9 year old boy in a street market in La Paz, Jess had a new pair of sunglasses with polarized lens for just $7 USD. A day later she realized she also had splitting head-aches from their vice like grip on the back of her head. I fixed that using a gas stove and a pair of pliers in South Africa. Before you buy anything in a market, take a real time and look it over, make sure it's not mildly broken and it fits you.
Socks are probably the one area where you may want to have more than two of a thing. Jess has two pairs in her pack. We generally adhere to the wear-one, wash-one philosophy, but socks get stinky faster, often dry slower and don't take up much space. As always, when you are using something constantly and have no alternatives, it's best to invest just a little more to make sure you get quality stuff.
Jess wears sandals more often than I do, especially in more formal situations. These aren't the most comfortable for all day wear but work great when we are going out for the evening to a nicer place. You can see they've got some wear on them, but are holding up so far.
This is Jess's second pair of Teva sandals that she brought on the trip. In contrast to my Chaco's, they are incredibly light. She uses them for any water activities or long days of walking. Especially in hot climates, we will go weeks without putting on shoes so it's been vital for us to have a good, comfortable pair of sandals for daily wear.
Jess and I both ordered several pairs of shoes from Zappos to test prior to the trip. We both ended up choosing Merrell's. It would be nice to find everyday-every condition shoes that looked a little less techy but you can't have it all. What we both have is really comfortable, moderately breathable and mostly water-proof shoes that have walked through cities, mountains and beaches on four continents. Shoes can be the bulkiest and heaviest single item in your pack, make sure you are buying something that will work for the long run. Zappos's return policy is great for trying a couple pairs together. Make sure you walk with a loaded bag and try them on with all the outfits you plan to bring.