You would think after numerous trips, foreign and domestic, short and long, that packing would be easy. Unless it is a quick overnight, I always take a decent size roller bag, and check it on the plane. I have about four or five different sized suitcases, depending on the destination, weather, and planned events. Obviously, going to warm weather destinations is much easier. During my business travel portion of my career, I ran into the worst of clothing requirements for the weather. I can recall one trip that started in Tucson (over 100 degrees) and ended in Seattle and Portland where it was raining.. And yet another, started in Palm Springs (over 110), and ended in Denver, where it was snowing. Boston and Atlanta were another unfortunate pairing. Bringing a business suit or two is not that challenging. Two suits, numerous dress shirts and ties, one pair of dress shoes are obvious. Add one set of casual clothes and sneakers for evenings or unplanned events. I usually put this in a garment bag, and rarely checked baggage. Packing for vacations is more difficult. And packing for a formal event (wedding or funeral) along with some leisure travel is a real challenge. Shoes are one obvious challenge. Two pair would be the minimum. Here a few of my tricks to help solve some of this travel conundrum. All three photos above are from the same trip: Chile and Argentina One is a focus on a single color, or at least one dominant color, with accessories. For business, it was always easy, navy blue or dark grey suits in winter, tan, light blue and light gray suits in summer. The trick was packing just one pair of dress shoes, generally some shade of brown or cordovan. Two, make sure most items are interchangeable, creating several outfits For example, a powder blue or white shirt will pair well with most any color. Three, wrinkle free is VERY important. Four, make sure your clothes make the transition from day to evening. Five, sun protection is important, in addition to suncreen. Long sleeves, hats, and sunglasses. Six, bug repellent and odor protection clothing, when necessary. Since many people start with basic black, I have gradually transitioned to navy blue, and blue. Both pair well with khakis and denim. And there is a plethora of packing trips for women, but very few for men. Here is my list for men, warm weather one week to 10 days. Just double it for a longer trip. BTW, I do a limited amount of laundry in my shower. My basic color is blue. Shoes: one pair of sneakers, one casual, but good for walking shoe (I always bring a pair of sandals for use in the hotel room or pool areas. Socks: 4 white, 4 assorted colors. Pants: One pair of denim, one khaki, and of course, the pair you are wearing on the plane! Shorts: one each tan, one blue, one fun (stripe or plaid) T shirts: 4 various colors, all hand washable (make sure one can be used for workouts in gym) Polos: 2 various colors, all hand washable Shirts: 2 basic button downs, one solid, one pattern, plus the one you wear on the plane.Underwear: 6, all hand washableJacket: one light, all weather jacket, worn on the plane.Optional items: 1 packable down jacket, i packable rain jacket, swim suit, cap, and large bandana.This fits in my roller bag, which I usually check. I also carry a sling backpack for my tablet, various cables, adapters, medication, masks, snacks, water, and spare change. Any other questions, please ask.