Not especially gifted with practicality, I took many trips and made a few ludicrous errors before I figured out how to do air travel with less stress. Here are my hard-won tips for packing, unpacking, and details in between:

1. Identify what combo of luggage works for you. Nothing will be perfect. (For example, customs and tech out/shoes off security will always be complicated, no matter what you do. You can make the experience worse, but you can’t really make it smooth. How could partially unpacking and removing several clothing accessories in under a minute go off without a hitch? I have to be kind to myself about that, while at the same time learning not to drop crucial paperwork.) For my trips, I often have to think of casual, town, and professional dress, with extra room in case I make some purchases at my destination—I need space. Then I can’t help but include just-in-case clothing items, which often turn out to be helpful. Yet I’ve learned that a giant suitcase is a bulky inconvenience. What works for me is a medium two-sided suitcase that rolls in any direction, a good-sized carry-on, and a backpack. I’ve done this for the last couple of trips, and it just may be my formula.
2. Be willing to pay extra for convenient travel times. Leaving at five am (a popular departure time) means getting up before three and arriving at the airport bleary and frazzled after a sleepless night waiting for your alarm. This will guarantee that you start your trip exhausted. I like to depart late in the morning to mid-afternoon. That often gives me time to get up and pack at my leisure rather than heaving items in my suitcase the night before. And I’d rather fly in somewhere late than arrive at nine am at the high cost of sleep. I’ll pay that extra $80 or $100 if I have to—and usually any savings for getting up early is not nearly worth it, anyway. A good travel time makes all the difference.
3. Realize what you can survive without. I’ve accepted that I don’t need my beloved cheap, generic-branded Bose experience headphones. They are too big, I don’t end up using them much, and I worry about them getting crushed. Tiny wireless earbuds are a lot more travel-friendly, and I don’t shrivel up and die without them. I can look forward to a wonderful reunion with my big, padded friends after my trip. (Can you believe I took those to England? And maybe used them once the whole nine days.)
4. Wear your heavier, bulkier clothes for traveling. Don’t be uncomfortable, but wear a heavier piece of outerwear and your boots, if you need to bring a pair. That way, the weight and bulk affect neither your carry-on nor your checked bag, and you are warm. (Of course, those boots will set off the security booth thingy in San Diego, so when you think the TSA has finally loosened up there, they’ll make you go back to take them off and set them on the belt.) You probably won’t regret wearing layers. The plane may get stuffy for a few minutes while on the tarmac, but once in the air, it can get almost chilly and stay that way the entire flight.
5. Find a decent backpack for your personal items. No purse, not even a large one, will be so convenient or store so much. If it’s needed, a small purse can fit inside. The backpack I inherited from my daughter has plenty of storage pockets, but what I love is that you can unzip the generous main compartment and see all your belongings in the various sleeves at one glance. For a somewhat hapless individual like me, this is perfect. The side pockets are secure enough for my wallet and important papers, so there’s no more struggle to retrieve and return these items. But pack it as light as possible. If you don’t have your carry-on roller bag with you, it may actually have to go on your back for long walks through the airport. And it’s amazing how seemingly light items—a Chromebook, a small iPad, a Kindle, a paperback, and a few printouts for work—can get heavy fast when all in one bag.
6. Take advantage of the carry-on when it’s allowed, when you haven’t purchased that rock-bottom ticket. It will allow you to wheel your backpack on it through the airport, as today’s backpacks should have one of those straps that allow you to slide it over the pull-out handle of your carry-on. And in the carry-on, you can tote all your extra shoes, your socks, the toiletry bag, a special pillow, and bulkier outerwear. Then you won’t be sweating the weight of the checked bag like I often have in the past. (Stress about suitcase fees is how I found out that my sister had this sixth sense for suitcase weights. She’d just lift, think for a bit, and then announce the number of pounds. She was always right.) I haven’t yet figured out how to travel without plenty of shoe options. And extra books.
7. If they’re offering to check roller bags at the gate, take them up on it. Then you can skip the step of struggling to pick that thing up over your head, like I do, and having to ask a nice man to help you. If you’ve checked a bag, you’re going to the luggage carousel anyway.
8. Try to cut back on the books. During the last few minutes of packing, I’m always stuffing in extra books for both leisure and work, and I need to stop it. I rarely get to read all of them, and many are sitting unread at home, anyway. If I really needed reading material, I could find it on my Kindle or at my family’s house. These add weight and take up space. But it still happens, every trip. I just . . . panic.
9. Roll your clothes. Avoid folding and stacking them in your suitcase. Then you can see what you have, and possibly fit more in. Also, rolled-up clothes probably fit more tightly, so they stay neater and prevent that jumble of items you don’t want to see when you open your luggage.
10. Prep for the plane ride once in your seat to minimize disturbing your seatmates. I tend to seem fidgety and always rummaging for something, keenly aware that the lady next to me, quietly absorbed in her downloaded media, just wants peace. So now, once seated on the plane, I pull everything I’ll want out of my backpack and place it in the net bag before stowing the bag under the seat. I like my iPad for that word game, as flying is the only time I treat myself to it, as well as a book and something for work. And my reading glasses.
11. Bring a hard copy of something to read if you want to work on your job in the airport and on the plane. I learned this because my little Chromebook for travel forbids me from connecting to any airport WiFi. So this last trip, I got a lot of reading and note-taking done. It was satisfying and easy, less of a headache than trying to get my tech going and desperately putting it away before boarding.
12. Find cheaper options if you don’t want to splurge on a meal. The (now $7) hummus and pretzel combo in the little convenience/gift stores is a way to almost get through a major chunk of the day without a proper meal. But also, the San Diego airport offers a $12 Phil’s BBQ plate with sausage and fries, which were delicious on the plane. In my Montana airport, the sandwiches are $17 and worse than mediocre; order a full meal at the bar, however, and you pay about the same price for good, hot food. By the way, Alaska gives out onion-mustard pretzels as their on-board snack. I think they want to prevent long conversations between seatmates.
13. Speaking of airlines, my best experiences have all been with Delta. I think they have good luck with their hub not being in Salt Lake or Denver. They are always early, have laid-back flights, offer movies if I feel like taking advantage, and often distribute nuts as their snack (and they’ll give out two bags). I’ve had little to no drama with them, at least not that I can remember. It seems like United almost always has a hitch, a delay. “We’re cleared for take-off. Unfortunately, folks . . . ”  Besides that, United’s pacing is frenetic. Once, I was barely done hefting up my carry-on when the attendant got on the speaker and insisted that we all be seated with seatbelts fastened. Um, can I get on the plane first? Delta has never felt like that.
14. Once at your destination, even when staying for days, avoid item creep. Try not to spread out to dresser drawers or medicine cabinets, even if you do hang things up in the closet. If you’ll be there for a while, choose one or two key locations and keep it at that. For me, limiting the spread of my possessions decreases my stress level and the degree of re-packing effort I have to invest. It prevents my having to think so much or needing to double-check for forgotten items once I prepare to leave.
15. Unpack like you’re doing the polar plunge: Dump everything on the bed and put away the empty suitcases. Done! Now all you have before you is a pile of clean laundry and some shoes to put away. I’ve spent years putting off unpacking for . . . let’s just say way too long before doing this trick recently and having the chore checked off my list by my third day home. I finished up by vacuuming my room, and it was a beautiful feeling.

I would love to know your best flying hacks. What gets you from point A to point C without unraveling?