I love to travel, but I hate luggage. I don’t like carrying it, I don’t like the idea of the airline losing it and I don’t like the time suck of keeping track of all of it. The more I traveled, the more I learned how to travel light, and at this point packing is a sport. Some would say Olympic level. It’s like a style puzzle to pull the fewest pieces of clothing that will yield the highest number of outfit options. My own, twisted packing algorithm that changes depending on the type of trip I’m taking, time of year I’m going and how long I plan to be there. Remember that scene in the movie Up In The Air, with George Clooney and Anna Kendrick? Where the streamlined packer Clooney character makes the overpacked Kendrick packer ditch half of her suitcase at check in? I’m Clooney, every single time.
There are tricks, of course. My advice? Start with a narrow color scheme (three neutrals and one pop of color), limit shoes (one pair you wear, you pair you pack), bring two tops for every bottom, one light weight blazer or bomber (depending on how profesh you need to be). Rely on solids that you can mix and match and use accessories, lots and lots of accessories, to change it up. I could go on, but that’s the framework. You know what it takes above all else? A total and complete willingness to be unbothered wearing things more than once. Maybe even more than three times. 
Case in point, a four-day trip to Miami. Me, two of my oldest friends, and four kid-free days of sun, sightseeing and snacking. I packed ridiculously light. I warned my besties that they would see a lot of one particular look, and they did: I literally packed one dress and I wore it. Every. Single. Night. It was one of my fave LBD’s: a stretchy material that isn’t too flimsy, with a draped, asymmetrical neckline, short sleeves, fitted body and mid-calf hem (with hidden zippers on either side to show a little (or a lot) of leg, depending on the mood). It’s a winner I tell you, and it also packs to the size of a bandana, sans wrinkles.
My bag of tricks (a.k.a, my accessories) was another story. I loaded up with all sorts of baubles—gold and silver, chunky and delicate, colorful and not so much—and included a few clutch bags (another great packable option) to wear with.
Here’s my advice:
All hail a good dress.
Choose something that fits well—body con but not tight—in as close to a four-season weight as possible. Avoid any fabric that wrinkles (satin and linen, I’m talking to you). I don’t personally like things that are too clingy (oh hey there cellulite!) so I go for a bit of structure.
Give yourself permission to dress it up or down.
Me, I rarely wear heels any more—they’re uncomfortable on my feet, they’re back breakers, and they’re impractical for, say, basic walking. Hence, I’m always on the lookout for dresses that look chic with anything flat, including sneakers, which, thankfully, are finally accepted as chic. I like longer flow-y styles, and also narrow, column styles that hit about mid-calf. No minis (trashy), and nothing with a full skirt that hit’s mid-calf (dowdy).
Sex it up
We’re talking evenings, after all, so a little sexy goes a long way. In other words, this is no time to be frilly or overly covered up. Skip the high neckline and prissy styling and go for fabric that feels good to the touch, in a silhouette that’s body con but not tight. Annnnnd show a bit of skin, go for either a plunging neckline, or plunging back, or a side slit for some leg…but never all three elements at the same time because, well, I’m no J. Lo and you aren’t, either.
Opt for something neutral.
If you want to wear the same dress night after night, you kind of want it to be forgettable. Not a snooze fest, but not a siren of a garment, either. Because the point is to mix it up with the accessories, and dark solids or neutral prints are more versatile, providing the ideal backdrop for whatever you want to layer on top. It’s also worth noting that dark colors hide spills and sins (see cellulite note, above). I also avoid dresses with sparkle or hardware so as not to conflict with my accessory options.
Plan your accessories.
Set them out, night by night, ahead of time. Employ different looks by using color, texture, weight, trend, etc. Here’s how Miami went down: 1st Night, The classics—diamond studs, layers of gold chain necklaces with personal collections of charms on them, EM necklaces in Caramel and Utility (olive green). 2nd Night, 70’s gold (big gold cuffs on each wrist, chunky gold rings) with two strands of EM necklaces, both Coal (black). 3rd Night, loads of Native American silver with turquoise stones (necklace, bracelets, earrings, rings, the whole shabang) with one EM necklace in Pool (turquoise). 4th Night, all the bright colored beaded bangles I bought in Mexico City, with massive beaded dangling earrings a friend brought me from her trip to Morocco), with EM necklaces in Bowie (chartreuse) and Party (raspberry).
Packing tip for accessories: I use old, hard-shell sunglasses cases to pack most everything (except my EM necklaces, which come with their own canvas travel pouches, FYI). The glasses cases keep everything safe, allow me to pack in groupings, and are easy to wedge into a suitcase.