I don't care what anyone says, packing properly is harder than actually planning and booking a vacation. Anyone can throw everything they own into a rolly bag, but it takes real skill to thoughtfully plan just the right mix of essentials to bring along for the ideal travel wardrobe.
Given I am on a plane several times a month, I have made packing my absolute obsession. And after a lot of trial and error (and way too many dresses that have gone unworn!), here's what I've learned:
1. Weather check. Yes, it's more fun to wing it, but so NOT fun when you're preparing for a dinner on a gorgeous 75-degree evening and all you have is a heavy wool dress. Boo! Take the time to check the weather and make sure that everything you do bring is climate appropriate.
2. Edit, edit, edit! Lay everything you really want to bring out on your bed, and then, piece by piece, take away half of what's there, leaving you with only the pieces you truly love wearing that you will feel good in. Traveling is never a time to "road-test" something you haven't worn before. If you haven't worn it on your home turf, you sure won't wear it somewhere else.
3. Extra accessories equal extra options. I absolutely never check luggage (such a time drain!), and I make sure the clothes-to-accessories ratio in my bag is always 1:2. Choose a few key pieces that create a bunch of flexible outfits, and then double the number of accessories you bring. One pair of flats, one pair of evening heels, a chic clutch, oversized earrings, matching cuffs, a statement necklace (or two!), and a few cocktail rings can make even your most basic outfit feel special and unique. And they take up the least amount of room in your bag.
4. The bag matters. That old overnight bag you inherited from your mom or your last boyfriend? Toss it. Immediately! Never, ever, ever think your travel bag doesn't matter. It may be "luggage" but it actually defines your travel look, and when it's great-looking and functional, it actually makes it more fun to travel with and pack.