Travel Like A Minimalist: How To Never Overpack Again

Photographed by Alexandra R. Gavillet.
I love packing, almost to the point where I anticipate it more than what I'm actually packing for. Even during road trips as a kid, I was the one who made sure that my pocket checkers set, sketchbook, and Walkman were tucked into my Ninja Turtles backpack and not in my duffle (which housed the five-or-so outfits I had picked out two weeks prior). These days, I've refocused my (debatably) obsessive planning to making sure I never, ever have to check in luggage, because if there's anything I hate as much as I love packing, it's having to deal with luggage. Two and a half weeks in China sightseeing and attending a family wedding? Just me and my carry-on. Ten days winding through the Cote d'Azur attending both ridic-fancy dinners and hiking trips? One. Carry-on. Only. Fashion Week in Europe in February? You guessed it.
But, my coworker, Gina, on the other hand, is an overpacker. Short weekend trips require rolling suitcases and anything longer than a week anywhere calls for a fleet of luggage. But, like me, she hates all the baggage that baggage comes with. Says Gina: "Despite my best packing intensions, I am often that girl wheeling a suitcase that's at least half my size, running through the airport, holding up the lines because my boarding pass has now suddenly fallen into the abyss of my oversized tote. Plus, because I pack so much, any trip that's more than four days, I always check my bag...and then get anxious it'll get lost in transit." So, to make sure she's spending her upcoming vacation actually enjoying her time traveling through Italy and not frazzled trying to keep tabs on her stuff, I offered to give her overstuffed suitcase a minimalist's makeover. Click through to see how we fit it all in a carry-on (with room to spare!)
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Here is a part of Gina's suitcase before we started in on it. With more than 10 complete outfits for her 10-day trip, the suitcase was still a good foot too overstuffed to close.

Says Gina, "I'm heading to a family wedding in Italy, but of course will be making the most of my time overseas. While the big bash will be in Naples, I've extended my stay to 10 days to be able to squeeze in a visit to Capri and some exploring along the Amalfi Coast. But, with all the things I wanted to bring, that suitcase wasn't going to close; I tried rolling, folding, and laying my clothes flats, but short of a miracle, there was no way it was all fitting."
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Tip 1: Don't think in "outfits;" think in "items."
If your pieces can mix and match, almost each item can be worn more than once without it seeming like you have the same outfit on. Here's a little bit of math to figure out how you can go about this: Take the total number of days you're going on the trip, and divide by five. Round up to the nearest whole number and that's the number of dresses or rompers you should bring. Take that number and multiply by three. Bring that many of shirts and bottoms. Going by that, you should have at least enough combinations to last the entire trip (and that's not even counting the pieces you're wearing to travel in).

In this case, Gina was going to be abroad for 10 days. She brought two dresses (one of them was going to be for the wedding — but more on that later), three tops, one skirt, one pair of shorts, and one skort.

One last thing — to ensure that you're never in a situation where you have to pick between a cargo short and another cargo short to go to a Michelin-starred restaurant, make sure that one of each of your bottoms can be considered "dressy." In this case, the leather skirt and chiffon button-down make for an ensemble that can be dressed up, but when worn separately, are still casual-feeling.

Doesn't look like a lot? Yep — that's the point. The hardest part will be reminding yourself that everything will be fine. "When Connie told me I was only allowed to bring three tops and three bottoms, I nearly broke out in hives," she says. "It makes perfect sense logistically, but I like options, and I was scared this didn't leave me with too many."

Gina's clothes, clockwise from above left: O'2nd Shirt; Carven Polo, Marissa Webb Button-Down; ASOS Skirt; Theory Skort; J.Crew Shorts; ASOS Salon Co-Ord; Need Supply Dress.
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Tips 2: Create a color and pattern story
But how do you know which exact piece to bring? The easiest trick is to stick with one color story, and throw in one or two complimentary hues to break things up. Gina has a lot of blues, blacks, and greens in her closet, so we mainly stuck with a palette of those colors, and added in a pop of persimmon through a pair of shorts.

Boring, you say? Well, not if you make sure you're packing a lot of prints and graphics, too — none of Gina's tops were "basic," but still matched with each and every bottom she had.

The ultimate secret? Matching sets: Worn together, they make a fancy outfit for a dressier evening out. Broken apart, they're a bottom and a top that can be mixed and matched with your other pieces. Gina's wedding dress is actually a slip and a cropped shirt in a pretty floral print that still match with her other pieces.

Gina's clothes, clockwise from the top: ASOS Skirt, Need Supply Dress; Theory Skort; Carven Polo; Marissa Webb Button-Up; Zara Scar; Uniqlo Button-Down; O'2nd Shirt; ASOS Salon Crop Top.
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Tip 3: Accessories are excessories. Leave most of them at home.
They're big, oddly shaped, and too easily crushable; when it comes to shoes, bags, and jewelry, less is more.

"I try to be conservative with how I pack shoes and accessories, but I probably would have packed one dressier heel, one shoe I can walk in, one less-dressy sandal, and one pair of beach-appropriate shoes," says Gina. "I also always pack a few handbags and shove them with any other accessories I might want to wear while I'm here. Yes, that's conservative."

Start your minimalizing by remembering that your travel outfit already consists of a pair of shoes and a bag. Beyond that, you really only need one more pair of shoes that work for dressier occasions (no matter how long your vacation).

For Gina's wedding, she had to devote some space to a pair of heels, but the lace slides were comfy enough to wear everyday and to the beach, but still looks shades more polished than a pair of flip-flops.

In terms of bags, you really only need two: a basic crossbody and your "personal item" bag (that should really be roomy enough to comfortably house the other). As for evening bags, double up by using a clutch as your toiletry bag (a plastic baggy liner helps keeps things spill-proof).

Gina's clothes, clockwise from above: Topshop Bucket Bag; Meredith Wendell Clutch; Zara Slides; Tibi Sandals.
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Tip 4: Create your plane outfit as you go.
Gina's travel outfit typically favors comfort over anything else: "I typically go for something comfortable (although not entirely schlubby) for the long plane ride, so I put on my coziest pair of skinny jeans, my favorite college sweatshirt, a pair of flats, and carry a scarf in my bag in case I get chilly."

But, it's important to realize that your body is also a vessel to carry your clothes. Take advantage of a plane's typically freezing temps to wear all your bulkier items, including your long-sleeved layers, a scarf that can double as a pillow, your jeans, and your "tourist" shoes (the ones you'll be wearing on days you plan on logging 15,000 steps).

And, even though Gina's heading to a warm-weather destination, chilly nights and random cold spells always seem to happen, even in the most unlikely of situations. So, it's typically a good rule of thumb to always bring a few longer, lengthier items.

Gina's clothes, clockwise from left: Uniqlo Button-Down; Comme Des Garcons PLAY Shirt; Amour Vert Jacket; Kate Spade Saturday Tote; Converse for Tibi for Hampden Shoes; Madewell Jeans; Zara Scarf.
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Tip 5: Dressing for the beach doesn't require a whole wardrobe
Gina knew that out of one of the days in her trip, she'd be hitting the beach, but she brought a whole kit of things. "I packed a beach bag that folded but still took up too much space, three bathing suits, a cover-up, beach sandals, and a small beach blanket." But knowing that she wasn't going to be spending her whole vacation shoreside, she really only needed one thing: her swimsuit. A longer tunic or dress is an easy cover-up, your hotel probably has towels to lend, and those aforementioned slides are great in the sand. Leave that beach blanket, other swimsuits, and beach-only coverup at home.

Gina's clothes, clockwise from left: Zara Slides; Marissa Webb Tunic; Madewell Swimsuit.
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Tip 6: Coordinate the items you don't need to bring with your friends.
Especially if you're going to be sharing rooms, check with your travel buddies to make sure you're not bringing multiples of items that can be communal. With hair-styling tools, bulky tech products, and even toothpaste, sometimes, you just need one.

Gina's mini Jambox is the most compact out of all her friends' speakers, so she's going to sacrifice the space in her suitcase (but she's going to leave her hair straightener at home since her friend is bringing one).

Gina's clothes, clockwise from left: Topshop Bag; Jambone Mini Jambox.
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Tip 7: Plan for "definitely attending" situations. Take any "maybe attending" situations as opportunities to go souvenir shopping.
In Gina's case, this wedding was the reason she was headed across the pond, so she wasn't going to leave her fancy outfit behind. She might only wear the heels and clutch once, but there's no way around it.

What she did leave behind? Her work-out gear. "I have huge aspirations for running during mornings on vacations — ya know, taking in the scenery at a sprint — but I also did the last time I visited Italy, and I never even took those sneakers out of my suitcase."

As for any adventures that might pop up along the way? Think about those as an actual reason to go shopping and pick up a sartorial souvenir to bring back home.

Gina's clothes, clockwise from left: ASOS Salon Co-Ord; Tibi Heels; Meredith Wendell Clutch.
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And here, we've got her fully packed carry-on suitcase that actually still has room to spare.

Scary looking? Too compact to believe? Trust us — this works. "Overpacking is like a safety blanket for me. I want to know I have everything I need in case of, well, anything. But, it's really liberating not having to check a bag and challenging myself to mix and match from my own closet. And, in case something unexpected comes up, I can just use it an opportunity (or excuse) to go shopping."