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?
"Misun." 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."
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?
"Misun." 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."
"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."