I Just Spent 6 Weeks Living Out of a Suitcase—Here's How to Pack Like an Editor
You'll be surprised how much you can squeeze into your suitcase when you use my tricks.
Six weeks. One suitcase. Okay, maybe a carry-on too.
But yes, I was able to squeeze dozens of outfits onto a quick flight and managed to have no “outfit repeater” moments during my time away from NYC to flee the cold. By the end of my travels, I had a very clear understanding of what actually earns its place in my luggage—and what absolutely does not. Packing like an editor isn’t about owning a perfectly curated capsule wardrobe. It’s about knowing yourself well enough to anticipate what you’ll realistically wear on the daily.
I took this specific extended trip because I was in need of a break from the bustling city life and craving family time. I spend well over a month bopping between Naples, Jupiter, and Miami. As a New Yorker, I’m not used to having a car, so the fact that I rented a Buick Envista and drove around gave me a sense of freedom I’d long forgotten. This trip had a big emphasis on casual, especially since it was January, a slower month for social events. Overall, I’m so glad I took the time to pause and start the New Year right.
Over the past few years, my packing strategy has quietly shifted. I stopped thinking in terms of outfits and started thinking in terms of systems: pieces that worked together, layers that I could duplicate with different items, shoes that could handle more than one kind of day. What follows isn’t a rigid checklist—it’s the mindset and practical tricks that made living out of a suitcase not only manageable but surprisingly chic. If you have a long trip ahead, you’ll want to read this.
The Packing-Day Process
If you're packing for a six-week trip, this is the day that is going to be an absolute mess. Lean into the chaos, as you're going to need to play around with what you have in your closet to create the perfect combination of clothing for your trip. I like to lay things out that I am planning to pack based on category. A pile for sweaters, another pile for activewear, a third for swim. Then I edit down even further after that, removing anything that I can't think of three ways to style.
Packing cubes have been such a game changer for my packing process. Not only do they compress the items you have in your suitcase, but it's also a great way to get organized for a long trip. I had a separate packing cube set aside for the weekend trip that I had specific looks in mind for. I will also separate by category so when I unpack upon arrival, it's easier to get everything all sorted.
The Loungewear
It might be surprising that I'm putting loungewear first, but this is the one category that I know for a fact I'll wear every day while traveling, especially on a trip that involves working from home. I surprisingly end up in elevated pajamas more than traditional sweats, as they feel dressed up. Sweaters, linen pants, and easily layerable items become key in this area as well.
The Activewear
I was on a mission to attend five workout classes a week during this trip, which made me care about what activewear I packed. Knowing I had access to a washer/dryer, I landed on seven active looks so that on the rest days when I went for a walk, I had something to wear without having to use the laundry more than once a week. The key thing to know about activewear is that it's all about how you style it. A different tee or tank on top, or an interesting jacket, a cool sports bra underneath, sweats over shorts, etc.—these are all many ways to make a set you've worn a dozen times feel brand-new.
The Daytime Basics
I actually impressed myself with the number of ways I styled this specific pair of linen pants. This category of my packing was inspired by the effortless and elevated basics that have risen in popularity among the fashion crowd. Think tees, jeans, button-downs… things you can truly wear on repeat.
The Dresses
An obvious category, especially for time spent in South Florida. A good dress goes a long way, and I brought several, styling them up and down depending on the accessories and letting them be the outfit.
The Swimwear
Another obvious choice for warm weather because who doesn't love a good swimsuit? I always pack a healthy combination of family-friendly one-pieces and IG-worthy daring bikinis.
The Outfit Repeating
Outfit repeating is a key part of this packing formula, but it's all about how you go about it. It's about strategy not just blatant repetitiveness. I pulled off wearing this dress three times but styled it differently each time. Different accessories, wearing a dress as a skirt, getting creative—it becomes a fun project when you're getting dressed in the morning.
The Special-Occasion Secret
I knew I had a bachelorette trip filled with special-occasion attire coming up on the calendar, so I allowed myself to pack just a few items I could only wear once. I tucked them away in a separate suitcase upon arrival and halfway through the trip was greeted by several things I hadn't worn yet. This made my wardrobe feel brand-new. If you're ever packing for a long trip, keep a few things hidden so that later in the trip you can feel like something is brand-new.
The Accessories
My focus in the accessories department was how can I wear each item up to 10 times. Versatility was truly key, as I packed sneakers that could be worn to the gym, to brunch, to the beach, and one more time just for the vibes.

Sierra Mayhew is a fashion editor at Who What Wear, bringing a decade of industry experience to the editorial team. Since joining in 2021, she has made her mark by blending luxury and accessible fashion, decoding runway trends, and curating must-have shopping lists. Before joining Who What Wear, Sierra sharpened her skills at Harper's Bazaar and Elle, with bylines in Bazaar.com and collaborated with iconic brands such as Gucci and Ferragamo. A graduate of the University of Notre Dame, Sierra translates editorial expertise into viral social content, making fashion engaging for a new generation. Her unique perspective is rooted in her love for travel, music, and discovering the hidden gems that make New York City a constant source of inspiration.