If you want to slip in another pair of sandals, it can be doable, but I do my best to stick to the two-shoe rule. If you’re going to a warm-weather destination, the sweater question is a moot point, but if you’re headed to Berlin in the winter, you’re gonna want a sweater or two. The secret here is to fill your suitcase with dresses (with tights, if cold), slacks, and shorts (if relevant to your destination), because you can fit way more of them. When I’m packing for a trip, I make sure I could wear every piece of clothing with multiple outfits. The key here is to pack solids — white and black tees, plain bottoms, and a neutral jacket. I swear by slip-on Vans, which are easy to get on and off at security, and zip-up sweatshirts, which are easier to get on and off than pullovers. Skip the chunky jewelry and belts, which you’ll have to take off and put back on at security anyway. I usually pack my laptop, Kindle, and chargers, as well as any snacks (I always bring a bar or two) and my bag of 3.4 ounce (or under) liquids. I put everything I’ll need to pull out at security (liquids, food, and laptop) at the top of my backpack so I can quickly pull them out at security and slide them back in after I make it through. And, since your carry-on will be stowed in the overhead compartment, your backpack should be where you pack everything that you’ll need to access during the flight, like headphones, earplugs, and water.
