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What to Pack: Clothing That Actually Works

My philosophy: pack less, wear more. Every item on this list earns its place in the bag.

Versatile travel staples

• Black cami — Goes under everything, dresses up or down. Worn in Chicago, Italy, and everywhere in between.
• Midi wrap skirt — Packable, comfortable, looks polished at dinner.
• Black romper — One piece that works for day sightseeing and evening out.
• Quality jeans — Two pairs max. One casual, one dark wash for evenings.

Shoes for every trip type

• Birkenstock sandals — Our go-to for warm weather walking. Comfortable from day one.
• Clark’s wedge sandals — Comfortable enough for hours of walking, cute enough for the theatre.
• Prana travel hat — Sun protection that doesn’t wrinkle in your bag.

Don’t forget

• Lightweight rain jacket — Packs down small, saves the day.
• Compact umbrella — Always in the bag, never regretted.

Full packing lists for specific trips are inside each destination guide.