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Carry-on only spring/fall packing list

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After years of travel for work and fun, I've boiled down my packing list to the following clothes for all trips other than super-hot or super-cold climates (items with * I wear on plane)

Rainforest ruffled black raincoat* (rolls up in a ball, wrinkles shake out)
Two pairs leggings (one pair *)
Three tunics (one *)
Pashmina* (works as a blanket on plane and in hotel, as a scarf when it's cold)
Low-heeled boots*
Black polar fleece gloves (you never know when you might encounter a cold spell)
Black polar fleece cardigan (layered under raincoat, plus scarf and gloves and I'm warm enough for almost anything)
One pair khakis (usually grey or black) with a little lyrca (I like Old Navy)
One short-sleeved and one 3/4 or long-sleeved dressy tshirt (I like Boden)
One pantsuit (if travelling for work) or one pair dressy trousers (if vacation)
One lightweight merino cardigan - preferably a bright colour or pattern (I like Garnet Hill)
Two pima cotton sleeveless shells (I like LL Bean; they go under my suit jacket and with the cardigan)
Charcoal grey Nikes that are stylish/sleek enough for sightseeing but also work for workouts
One fitness tshirt
Undies and socks (usually pack at least 4 pairs of socks because they take longer to dry than undies if you handwash them)
Lightweight cotton menswear style pajamas (wearing pajamas when I'm in my hotel room saves my clothes for going out)
Loafers that are dressy enough to wear with suit etc but comfy enough for walking around
Small umbrella
Bathing suit (tankini) - because you never know when you'll find a pool

This packing list takes up about 2/3 of a 20" rollaboard. Then, depending on what I have planned, I'll add either a skirt and sweater, an extra suit (e.g., if it's a business-only trip with a week's worth of meetings), a lightweight roll-up-in-a-ball knit dress, or a couple of extra casual tshirts.

Toiletry kit contains:

Travel size facial moisturizer
Deodorant
Toothpaste and travel toothbrush
I use hotel soap, moisturizer and shampoo so don't pack any
Migraine meds
Ibuprofen and tylenol+ codeine (I have a bad back)
Steroidal anti-inflammatories (emergency supply in case my back goes out)
Mosquito repellent in wet wipe packets
Antihistamine (because I swell up like a balloon when bitten by bugs)
2-day supply of cold meds (because sometimes you don't have time to get to a pharmacy for a few days)
Immodium (I travel to developing countries a lot)
Cipro - antibiotics (see above re travel to developing countries)
Melatonin - helps me sleep on planes and get over jet lag
Ear plugs
A few bandaids
Tweezers

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