We Tried It: An Obsessive Overpacker Attempts Packing for a 16-Day International Vacation Using Only a Carry-On

What It Is: Learning to be a better packer by following the directions in How to Pack: Travel Smart for Any Trip by Hitha Palepu

Who Tried It: Sharon Kanter, PEOPLE Deputy Style Director and Obsessive Overpacker

Level of Difficulty: 8/10 (because packing gives me anxiety)

Packing stresses me out. What usually ends up happening is that I pull an all-nighter the day before the flight, trying on a million outfits, packing a million outfits, and getting in a cab to the airport sleepy-eyed and annoyed that I have to deal with checking a bag. Only when I would arrive at my destination would I figure out I didn’t pack enough warm clothes and end up not wearing half of the pieces I brought anyway. Tears would ensue. Some prideful shivering, too.

So, when I planned a 16-day getaway to Italy and Greece this summer, I vowed to have a more stress-free packing experience. Then, I took it one step further, and challenged myself to only pack a carry-on (a smaller European size at that!). If it seems like self-inflicted torture, it was actually more painless and liberating than I ever could have imagined. I feel like I’ve seen the light. I won’t go back. It’s carry-on life forever, whether it’s a long weekend or a long vacation.

And that’s all thanks to the tips and tricks I learned from Hitha Palepu’s pocket-size book How to Pack: Travel Smart for Any Trip. Yes, I had to read a book on how to pack. And YES, it was worth it.

Here’s what I learned:

The first step is admitting to yourself that packing is not easy. If it comes naturally to you, then awesome. Grand. You get a gold star. But if you’re like me, it doesn’t. This is a skill. It takes practice. And work. Palepu describes four “packing personalities” in the book, and you’re probably one of them: The Anxious Overpacker, The Forever Forgetful, The Jumbled Traveler and the Impractical Daydreamer.

I’m the first one. “You fear not having something you think you might need. You need options, even if the options are all similar to one another.” Recognizing what kind of packer I was right away helped me become more conscious of how I needed to approach this challenge: Ruthlessly edit, edit and edit some more.

“You spend months planning a trip, right? So, why are you packing the night before?” Palepu writes. I think this was the moment, page 12 to be exact, when I screamed into the book and said, “Where have you been all my life?” Her tactic, plan your packing like you do your trip, was so simple and yet so true. I detail my itinerary to death, and I can’t believe I had never thought to take the same approach to my suitcase.

So I started early—like two weeks early. I carved out a space in my apartment (Palepu calls it a “packing station”) where I would just stash anything I think I might need on the trip. At first, I set aside tons of items, and slowly but surely, I took things out, switched things in, took more things out, and so on. I did this for about a week, spending about 15 minutes working on my mix every night.

Palepu suggested keeping your toiletry “bag stocked with travel-size versions of everything you know you’ll need.” That way, you’re always ready to go if some amazing getaway opportunity comes your way. Brilliant!

So I basically created three kits: One for liquid toiletries (all in TSA-approved sizes), one for dry toiletries like makeup, and one for my eye-care and medicine. I spent some decent time in the Bed, Bath & Beyond travel aisle getting duplicates of everything I needed, and spent about $39 on travel toothbrush, mouthwash and toothpaste, travel shampoo and conditioner, a pill case for Advil and Tylenol, travel-size Band-Aids, eye drops, travel Febreeze, travel Wool-ite, and more. (The Wool-ite came in handy the most: I washed my socks and underthings midway through the trip and was able to pack less of each.)

I actually did a dry run for the makeup bag the week before, using it both for a day look and an evening look. Doing the dry run made me realize that I overpacked it, and took out some things (like false lashes, two extra mascaras, an extra blush) so it was really edited down to only things I would use and need.

This one’s a heartbreaker, but the truth is you won’t wear them. Palepu says that you think you become someone else on vacation, like someone who suddenly wears sunhats with quirky sayings and rainbow sundresses. But, you don’t! So you’ll want more options that make you feel amazing than things you can only wear once just for the ‘gram.

Sure, if you want something fabulous—for me, it was a one-shoulder pink lace Alexis top that I could not part with—by all means bring it. Those are what Palepu calls “fantasy pieces.” She just suggests that you only take one with you for trips that are three to five days, and no more than three no matter how long the trip is, even if it’s 16 days.

In the end, I brought this top, which I wore three times, and a blue dress that I didn’t wear at all. Jeez, she was really right about this stuff.

Palepu sold me on the idea of power pieces. They’re different for everyone, but they reflect your personal style, says the author. They’re what you can’t live without. What you turn to more than anything else. You know they’ll fit, no matter how many gelatos you plan on eating. Mostly, “they look good on you 100 percent of the time.” We all have ‘em.

She suggested picking the pieces you could get multiple wears out of to maximize their “power.” For me, that meant skipping dresses in favor of separates, like tanks, tops, shorts and skirts that I could mix and match to create as many outfits as possible, while still making each look feel new and different. My power pieces ended up being: white shorts, a white tank, a black dress, a white cardigan and a white denim skirt. I built the rest of the wardrobe around that.

This one’s a tip I picked up from my co-worker, Fashion Market Editor Sarah Ball. If you really want to pack smart, pick a color scheme—mine was Italy and Greece-inspired red, blue, white and black. It made mixing and matching outfits that much easier.

Tops:

Bottoms:

See, they all match!

I applied the same two tips above—power pieces and color scheme—to my workout items, though the hues here were navy, black and white. And while Old Me would pack one outfit per day that I planned to work out (which would have been eight outfits and a totally would not have fit in my suitcase), instead, New Me only packed three bottoms, three tops, and three sports bras.

I also made sure that the only ones that made the cut were made from the moisture-wicking fabric (my picks were Adidas, New Balance, Nike and Tory Sport), so that they dried quickly after each use. Plus, I wore one of these looks on all of the travel days.

This is where I have often failed in the past. This time, I followed Palepu’s amazing accessory equation. “Following this rule will drastically change the way you pack,” she writes. “Everyone overpacks accessories, thinking they are small. Stick to the math!” The math is this: Three pairs of shoes (heel, flat, sneaker), two bags (crossbody and tote), one scarf and one pair of sunglasses, with a hat and belt being optional.

And I’ll tell you what: This equation works! I brought four shoes (two going-out flats—instead of heels—a runaround sneaker and a pair of gym shoes), two sunglasses (I know she would oppose, but I felt like it was a necessity), two bags (one crossbody that doubled as a going-out bag and a tote), and no belt. I even snuck in one of those backpacks that fold up as a bag to bring to the beach. I had just enough. Not too much or too little.

“Your friends will help you edit out what isn’t necessary and give you the confidence that you are packing all the right things,” says Palepu. When I read this in her book, I thought it was silly. But I had my mom coming over anyway, so I asked for her input. It actually ended up being a game-changer: She took out a crucial pair of wide-leg palazzo pants, which opened up a lot of space to fill with other more important items, and encouraged me to bring one more sweater, which went on to become one of my power pieces. It helps to get a second opinion. (Thanks, Mom!)

OK, so what “made the bag?” This is TMI at its finest, but I truly think that a packing list can help you visualize exactly how much you need, and more importantly, how much can realistically fit. This is what worked for me…

• Toiletries (eye care + plane essentials/what I’d keep handy on a long flight): Makeup wipes, eye drops, contacts, glasses, fold-up toothbrush, toothpaste, pill case with Advil and Tylenol, hydrating face masks, headphones

• Toiletries (makeup): Nail file, bronzer, bronzer brush, eyeshadow, highlighter, two mascaras, brow pencil, blush, blush brush, concealer, eyeliner, three lipsticks (pink, red and berry), lip balm and lip sunscreen

• Toiletries (liquid): Sunscreen, shampoo, conditioner, Febreeze, tinted moisturizer, mouthwash, body oil (which I put in a smaller travel-size container), deodorant, coconut melt (used for makeup remover and a hair mask), Wool-ite (for washing underthings), bandages

• Accessories: Fold-up backpack, crossbody, tote

• Earrings: 10 pairs (I splurged here because they were so small!)

• Shoes: Two sandals (one light, one dark), runaround shoes, gym sneakers

• Bottoms: Shorts (three pairs), skirts (two), pants (two)

• Dresses: one black, one striped, one blue (never worn), one white/blue (wore once, barely, could have lived without it)

• Tops: Sweaters (three, only wore two), tees (two), going-out tops (three), button-down (one, worn as a coverup), tanks (three)

• Workout gear: Bottoms (three), bras (three), tanks (three)

• Swimwear: One-pieces (two, doubled as bodysuits), bikinis (three)

• Other essentials: A Kindle pre-loaded with five books (for space-saving reasons), my computer, my chargers (yes, multiple), my S’well water bottle, a travel wallet with Passport and an irrational supply of hand sanitizer

Verdict: If you have the time to invest in following Palepu’s tips for packing smarter, do it, do it, do it. Ultimately, all the work ahead of time saved me tears, stress and anxiety. It also made traveling so much easier, (especially since we went on four flights, four one-way trains, two car transfers and one ferry), as well as made picking outfits every day so simple since everything already matched.

Honestly, the last thing I wanted to do on vacation was worry about schlepping all my unnecessary crap around. It’s vacation! I had relaxing to do—and oh, did I relax!