Packing Tips From A Badass Style Editor

We're no strangers to a little separation anxiety from time to time. While goodbyes can be tough, the real tearjerker is when you pack for a trip and have to leave the majority of your precious belongings behind. If only we could bring our entire closet to accommodate every possible scenario — white sneakers were not meant to be worn with everything, right? — but such is life.

Fashion folk, you feel us. Squeezing your multifaceted, ever-evolving style into a pint-sized valise seems like a near-impossible task. But, with advice from senior style editor Annie Georgia Greenberg, you'll see that even with a few simple pieces in tow, you can stay true to your trademark look. Whether she's hitting up Paris Fashion Week or covering the red carpet at Life Ball, Annie's life out of a suitcase has made her a pro at whipping up Insta-worthy outfits on the fly that also fly well. Read on for how she does it, her go-to vacay looks, and what travel shoe she swears by (hint: it's not a sneaker). Then, head over to Gap for another dose of AGG's style wisdom.

Describe your style in three words.
"Evolving every day."

Are you more of a frequent flyer or a long-distance driver?
"I love road trips! The journey is part of the whole thing."

If we pulled you over on the highway, what music would you be playing?

When it comes to vacation outfits, do you strategize or wing it?
"If I have a certain event on the vacation (a special dinner or outing), I'll try to pre-plan, but I'm a chronic over-packer and usually just throw everything in and hope it works!"

Do you have a personal packing motto?
"It will fit."

What's your hack for making it all fit?
"I max out my carry-on by putting jewelry and makeup into clutches and carrying an extra pair of shoes."

What are your styling tricks for creating multiple outfits out of just a few items?
"One change can make all the difference — try cuffing a sleeve or untucking a T-shirt to switch up the vibe."

When you're packing for a work-related trip, how does it differ from when you're packing for a vacation?
"I am a little more creative with my outfits [for a work-related trip] because vacation means more casual (and, in the summer, more jean cutoffs). I always make sure to have a white button-down."

Do you have any packing don'ts or items you absolutely won't bring?
"Don't bring anything you haven't worn in a while. If you don't wanna wear it at home, you're not gonna wanna wear it when you're far out of your comfort zone."
What clothing items will you never travel without?
"White button-down, flats, day-to-night dress, sunglasses."

Tell us why these two outfits featured would wind up in your bag.

"You can make a T-shirt feel more festive by going longer with the hemline and pairing it with '70s printed flares. Big on top and bottom is always a good idea. And, nude and flesh-colored looks are polished and sophisticated (especially if you keep styling sleek) and are perfect for summer workdays no matter where you are. I also never leave for the airport or train without a white button-down because it can be worn with jeans and high-tops or a chic short suit for a summer business meeting."

What is your thought process when putting together an outfit — what do you start with?
"It's almost always about the shoes."

You can only squeeze one pair of shoes into your suitcase. Sneakers or heels?
"Mid-height sandals."

Do you have any rules for travel style?
"Be comfortable. Layer. My go-to travel outfit is mom jeans, a T-shirt, and a leather jacket with slides. I always keep lipstick, moisturizer, eyeglasses, a book, and a journal in my carry-on."

Do you factor workout clothes into the packing equation?
"Yes! They're small and easy to roll up, so I usually try to squeeze in at least one pair of leggings. Sports bras can double as crop tops if styled properly, and I wear sleeping T-shirts for runs."

How do you get your suitcase up and down the stairs in your fourth-floor walk-up?
"Just take a deep breath and heave ho!"

What's the craziest thing you've ever packed?
"One time, coming back from a work trip to Savannah, I brought antlers from a local vintage shop. I had to bring them on the plane. The TSA was very confused."

Where are your next stops?
"I'm going to try to maximize every weekend this summer, plan something for my birthday, be back-and-forth from L.A., and spend a week in Martha's Vineyard for the first time. But, I'm most excited to see what impromptu trips and road trips I can fit in."

More from Styling Tips

Sometimes it can feel like life is just a constant rotation between large plastic bins of clothing — as soon as you're finally getting settled into your ...
Sometimes, looking a certain height is all about perspective
You can switch out your clothes all you want, but you can’t really replicate the way glasses can completely transform you. It’s like presenting an ...
If you're like us, Beauty and the Beast was in heavy VHS rotation when you were a kid. And, if that's the case, there's a good chance you were as besotted ...
No matter what country you came from or what country you're headed to, first-generation immigrants have a tricky relationship with fashion. What's normal ...
When you're young, you get used to being asked what you want to be when you grow up. But why should that stop when you actually reach adulthood? You don't ...
This story was originally published on August 4, 2014. Even though we've all experienced most temperatures, we have selective memory about what they're ...
(Paid Content) As cooler temps signal us to switch up our wardrobe, it's tempting to go on a sweater-weather shopping bender. But considering all the fall-...
If you've ever looked at model-street-style roundups and said to yourself, Gosh, I could never afford that, or even, Yeah, but they get all that stuff for ...
Cutouts have always seemed like a really daring thing to wear, especially if you were the kind of woman who wore bras most of the time and didn't consider ...
You know this meme. You might feel closer to it than any other meme that's ever memed. It's at once an admission that things are close to ruin all around ...
There's maxi-length, which goes down all the way to the floor. There's knee-length, which hits at or below your knee, midi-length ends right below your ...
For women who subscribe to that Rachel Comey lifestyle (martinis over rosé, Brooklyn over Manhattan, jumpsuits over gowns, Bowie over The Beatles), there's...
So, there's that outfit that's been stuck in your brain ever since you came across it in a slideshow once, not only because it's really good, but also ...