Packing light is easy. My wife and I each travel all over the world with only a regulation (21x13x8 inch) airline carry-on bag with wheels, even when cruising. This allows maximum flexibility and peace of mind.
When cruising I take three outfits: one formal, one informal, and one casual. The formal outfit is a black suit with white shirt and tie; the informal is a sport jacket with matching shirt and slacks; the casual is a knit shirt and nylon pants. I wear black shoes with rubber soles. In the tropics I add a T-shirt, shorts, sun hat, Teva-style sandals, and umbrella. In cool climates I add a turtleneck, polypro sweater/jacket, a warm cap, and a Goretex-type rain jacket/windbreaker.
My wife’s travel clothes are analogous – she packs cocktail slacks and a designer jacket for formal wear; a sweater, blouse and black slacks for informal wear; and a knit top and nylon slacks for casual wear. She also takes a pair joggers, Teva-style sandals, and (on cruises) low heels.
Microfiber clothes don’t need ironing and they can be hand-washed in the evening, towel-wrung, and hung in your room at night (we pack a few lightweight plastic hangers for this). The clothes will be dry by morning. Leave your blue jeans at home (you’re not that young and they’re not that practical). Don’t worry about impressing any "fashionistas" onboard your cruise ship -- they are more interested in what they themselves look like than what you look like.
A good guidebook with maps makes all of the difference when traveling, even on a cruise. I recommend Rick Steves guides for major European cities and Lonely Planet guides for great maps and details about every other corner of the world. Not having a guidebook makes a cruiser dependent on package tours, which are usually high quality but relatively expensive, and they may not cater to a cruiser’s personal interests. Photocopy the guidebook chapters about your ports of call so that you can carry just a few pages ashore and discard the copies (or give them to your steward for his/her shore leave) after you have used them. Pre-cruise reading is the best investment you can make in getting the most out of your vacation.
John Lawrence, the cruise director on our Star Princess departure deserves special mention at this point. He provides the very best port of call information we have ever encountered on any cruise. He does it with clear directions (and photos) of how to travel to (and within) each port city on your own using public transportation. He includes great background and sightseeing information for each port. Fortunately his presentations are repeated on your cabin TV the evening before each port of call. He deserves the Nobel Prize for cruise directors! None of our previous cruise directors has come close in this important service.
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