Whoa. Hi there! Nice to see you again. Sorry I missed a couple days … I've been traveling a LOT, like, three-cities-in-three-days-lot, which accounts for my recent absence. (And for this post, a packing how-to.)
First off, a disclaimer. There is, of course, more than one way to pack for a trip, and more than one kind of trip. These instructions will be of no use to you if you are planning a six-month scientific expedition to the Arctic or the Amazon, have to attend four black-tie balls in five days, or have a lady's maid or valet. (if you have a lady's maid and are packing your own suitcase/valise/trunk … why do you have a lady's maid?). These instructions are really only good for fairly boring businessy-type trips, or short vacationy-type trips. But, that said:
1. The first rule of packing is to know your own strength. If you are planning to carry on a bag and cannot lift it above your head, you should not be carrying on that particular bag. (Obviously, if you are disabled and know you will have help in any case, this doesn't apply to you.) But packing more than you can lift is a recipe for disaster and will cause irritation to all your fellow travelers. In a similar vein, if you cannot drag your suitcase without it toppling over, you might want to rethink that eighth pair of shoes. Not only will your transit to the check-in line be wobbly and fairly ridiculous, the airline WILL charge you for the overweight.
2. The second rule of packing is to know your own style. This, of course, is something you should know for your whole life, not just for traveling, but you should especially know it for traveling. I hate and despise those traveling clothes that strip every last ounce of your personality from you in the service of being "easy to pack". (That dress in the link doesn't even have pockets! How is that travel-friendly?) When you travel, you should look like a concentrated version of yourself, in that your clothes are the ones in which you feel most like you. You'll be out of your natural element, so you can't rely on environmental clues to give folks an idea of what you're like.
For me, this means I usually pack a lot of dresses (duh), bright cardigans to wear over them, and, for the airport, A-line skirts with pockets.
Wearing the same thing every day (and/or washing things in hotel bathrooms) is not worth it. If you wash something, it never dries (and who wants to spend their time doing laundry on a trip?), and if you plan to wear something every day someone spills something sticky or stinky on you. Better to just pack an extra dress.
3. In my opinion, jeans are overrated. Unless this conflicts with Rule 2 for you (in that jeans are the clothing in which you feel most like yourself), ditch the jeans. First off, jeans are boring. I don't care how designery they are, or what unique combo of leg width-wash-waist level you've chosen, they are, in the end (and on your end), just a pair of jeans. My other beef with jeans is that they often act as an (overused) safety net. How often do people pack a week's worth of clothes but then end up wearing jeans every day? Travel should be broadening! (And, I hate to say this, but if you're going to a major metropolitan area, wearing something OTHER than jeans and sneakers will help you not look like a tourist, if that is a goal for you.)
4. Check the weather. Seriously. You'd be surprised how many people just assume the weather where they are going is just like the weather where they are. (You can't assume, for instance, that San Francisco in June is going to be warm.) There's this thing called the Internet, and a large part of it is just weather forecasts. I also understand there is an entire cable television channel devoted to the weather. Don't just check the forecast — check the average highs and average lows, too. And, on top of that, bring a sweater. Just in case.
5. Make a list. In fact, make several lists. I like to print out a calendar page (you can do this from Google Calendar pretty easily) and write down, for each day, what I'm planning to do, which then guides what I'm going to wear. A day spent in meetings will have a different wardrobe than a day spent traveling, sightseeing, or working in a hotel room. Pack the list! If you're traveling for more than a few days it's easy to forget what you were planning to wear when. Make the list very detailed, right down to your underwear. If the dress needs a slip, write "slip" on the list.
Make another list of things that you need that aren't clothes. I like to bring my vitamins (in an old-lady case), Emergen-C, a stretchy exercise band (to help me counteract bad office chairs), a little sewing kit, etc. If you travel a lot save your "extras" list and print out a new copy for every trip. Why remember more than you have to?
Do the same thing for toiletries — there's no percentage in taking up mental space remembering whether you packed a toothbrush or not. Make a list and check "toothbrush" off it. If you travel more than once a month, keep a toiletry set all packed and ready to go. (When you come home from a trip, replenish it right away.) I like to keep two sets packed: one in a quart ziplock bag for carry-ons, and a larger one for when I check baggage.
If it's a work trip, you should also have a work checklist: laptop power supply, charger for phone, ethernet cable, etc., etc.
6. Use packing cubes. I know they seem gimmicky, but they are so useful. First of all, they make life easier for the TSA, and you really don't want to piss them off. Which would you rather have a stranger do: pick up your nicely-packed cube and peer under it, or rummage through a suitcase full of loose clothes, possibly dumping them on the floor? I've seen that happen, and it's ugly.
7. Shoes. Here's my rule for shoes: For any trip longer than three days, you need two pairs of shoes, but no more than three. (Four, maybe, if you have to bring a pair of fancy shoes for a party.) Two pairs is so that if your shoes get wet, or cause a blister (which they shouldn't because you have also packed an anti-blister stick to use on your feet), you have a pair to switch off to.
Also, if you bring the bare minimum of shoes and develop a sudden need for another pair, you now have an excuse to go shoe-shopping.
I don't have to say again that you shouldn't be wearing flip-flops in the airport, right?
You should not be bringing more handbags than you bring pairs of shoes, unless you are Judith Leiber.
8. Miscellaneous suggestions:
— if you haven't worn the thing you are going to pack in more than a month, try it on before it goes in the suitcase.
— always bring one more pair of underwear and socks than you think you will need.
— don't stress about wrinkles. Most hotels have fairly decent irons and ironing boards, and it takes less time to press something than it does to worry about what's going to wrinkle and what's not. I can usually iron everything I've packed in less than half an hour, while watching the hotel television (and there's always an episode of Law and Order playing in every hotel room, everywhere, at every hour of the day or night).
— shoe bags are nice. I'm just saying.
— special travel pillows, special travel alarm clocks, special travel hair dryers — all overrated. Unless you have a serious princess-and-the-pea sensitivity, you'll get along just fine with whatever's at your destination. (I don't get travel candles at all. Raise your hand if you think it's a good idea to light small smelly fires in a hotel room.)
— think: what would be the most inconvenient and irritating thing to have find in the city where you're going, on the trip you're planning? ("sanitary" supplies? A spare power supply for your laptop? Your special moisturizer? ) Bring extra of that.
— if there's any chance that you will be getting in late, make sure your toothbrush, face wash, and pajamas are the easiest things to find in your suitcase.
My suitcase from trip before last:
I know I haven't said anything about rolling vs. folding, or how to cram your socks into your shoes to save space, compression bags, etc. I find I rarely need to do any of that stuff. I put the clothes in the cubes, put the cubes in the bag, take one last look at my lists, and go to sleep early enough that I can wake up in time to make my flight in the morning.
Have a good trip! Send me a postcard.