Pack to Your Heart's Desire or Play it Safe?

2 writers face off on the age old question: To check or not to check your bag.

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For: Checking a Bag

Despite my best efforts, I've never been a successful minimalist. While I've managed to edit down my daily essentials to a wallet, a lipstick, and an iPhone 6+—all in support of the mini-bag revolution—I refuse to revise my thinking when it comes to packing a suitcase for a trip. My commute is frequently predictable; my vacation should be anything but.

Isn't it more exciting to let a suitcase function as a smaller, portable version of what is likely a delightfully random closet?

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I guess I could only pack items that would work with a specific itinerary. (Assuming I have one.) But why? Isn't it more exciting to let a suitcase function as a smaller, portable version of a delightfully random closet? Even if I'm destined for 48 hours in Boston, I always check the biggest bag the TSA will allow. (George Clooney in Up in the Air and Ben Stiller in Meet the Parents make the carry-on seem so depressing, don't they?)

There is something to be admired here.
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The shoes alone—a pair of flats and a pair of sneakers, something fancy, something to run in—require an actual, full-size suitcase, to say nothing of the space needed for beauty essentials and a scented candle. I'm an adult; I have needs, and among them are full-size bottles of Tata Harper's Rejuvenating Serum and Davines' Alchemic shampoo. Clothing-wise, I throw in every single thing that I recently felt good wearing, then I mercilessly edit pieces out, one by one, until I can zip my Rimowa shut.

On vacation, dress for the mood, not the occasion. And that should generally be quite festive, no?

Using my method, you'll likely arrive at your destination accompanied by an embarrassment of riches. When I brought a ruffled jacquard Marc Jacobs cocktail dress to the Atacama Desert, in Chile, my travel companion was agog. But I found it much more appropriate attire for enjoying enjoy pisco sours in front of a million-dollar view than zip-off running pants.

Alto Atacama Desert Lodge & Spa, Antofagasta Region, Chile.
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On vacation, dress for the mood, not the occasion. And that should generally be quite festive, no? And what's the worst that could happen? Let's say you end up in Stockholm with sixteen tops and a lonely leather miniskirt. Now you're practically required to do some damage at the Acne flagship, or, better yet, embark on an impromptu exploration of the vintage scene.

Judits Second Hand, one of the best vintage clothing stores in Stockholm.
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Once, my suitcase was delayed in the bowels of Malpensa Airport as I was en route to Milan Fashion Week. With just three hours until the Cavalli show, and only the Uniqlo sweats on my body to get me there, I asked my taxi driver for some ideas that weren't, you know, the Prada store. He suggested a brief detour to a top-secret Marni outlet. Salvation…and adventure! And isn't that kind of the point?

Here are five suitcases you'll be proud to claim at the carousel:

A50 Set, $595, raden.com.
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Brilliance alert: Raden's high-tech cases feature location technology, a built-in scale, and even two USB ports for charging your device of choice.

Topas Sport Multiwheel Packing Case by Rimowa, $1,190, nordstrom.com.

This lightweight workhorse is ideal for those who want to travel with eight pairs of shoes but not get hit with an excess baggage fee.

Goring Leather-Trimmed Fiberboard Travel Trolley by Globe Trotter, $3,665, net-a-porter.com.
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This option is extremely stylish, even though the leather, which is sure to be scratched while in transit, makes it a borderline impractical choice. But any globe-trotter will tell you that such marks add character!

Tegra-Lite Max Large Expandable Packing Case by Tumi, $945, tumi.com

The key word here is "expandable"—this behemoth can grow an extra two inches, which means you can bring roughly eight more tops and three more cute little jackets on your multi-week adventure around rural Japan.

Polycarbonate Classic 28-inch Spinner Luggage by Zero Halliburton, $995, barneys.com

Against: Checking a Bag

There are few things worse than the anxiety of waiting for your luggage at baggage claim: The aggressive crowds around the carousel; the fear that your bag won't ever arrive; the spiraling thoughts about your favorite dress lost forever in some kind of evil airline vortex! Worst of all is the knowledge that the time spent waiting for your bag could have been spent starting your vacation. Save yourself the uncertainty and anxiety and just carry on.

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This happy traveler just carried that bag on with her.

The truth is, you can fit everything you need into a good carry-on suitcase, and if you know how to do it right, you won't even need to deprive yourself the luxury of a little over-packing. I once fit five skirts, four pairs of pants, nine shirts, three sweaters, and six pairs of shoes into a small carry-on. Was my bag too heavy for me to lift into the overhead compartment by myself? Absolutely! But there are always nice people around to help you with that kind of thing.

Be vigilant—there is always overhead space somewhere!

The most compelling reason for carrying on is to save time, so let me break down a few key elements to perfecting the art of the carry-on:

  • Check in online, choose digital ticketing, and save yourself the trouble of dealing with a check-in agent. You can go straight to security if you don't have a bag to check!
  • Choose an aisle seat toward the front of the plane. It will set you up for a swift exit.
  • Save the $25 or so it costs to check a bag and put it toward taking a cab to your destination. Time saved and transit agony avoided!
  • If you're me and you're flying home, your mom won't have to drive around passenger pick-up 100 times because your bag hasn't come through the carousel yet. (Saves nice moms time, too!)
Money saved on checking a bag is extra cash for your taxi to the hotel!

If this all sounds very practical, it is. But it also doesn't mean you're just bringing one black dress along with a few scarves and necklaces to "spice it up." On a recent trip to Miami, I achieved carry-on gold status (that's when you wear everything you packed at least once and don't feel like you're compromising on style). My perfect formula: one pair of skinny jeans, one pair of high-waisted, wide-leg pants, four shirts that go with both, one simple but colorful dress, a light sweater, a light trench, and a coat for departing and arriving in New York, depending on the season. I also fit four pairs of shoes, all my makeup and toiletry needs, and two swimsuits.

An expertly packed bag means a smaller bag, always.
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Where's the fun in all this forethought and pragmatism, you ask? If you're anything like me, part of the excitement of the trip is the preparation (and knowing I'll spend the minimum amount of time at the airport necessary)—and a big part of being a travel pro is in the pride of a bag well-packed.

Want to be the most organized traveler on your next trip? Here are some bags to help you get started on your quest to carry-on supremacy.

Spectra Global Carry-On, $299, swissarmy.com.

This ultra-light suitcase (just over six pounds when it's empty!) is your new best friend. It's affordable and durable, with plenty of space and two interior pockets.  

Bellagio 21
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This handsome case will make you feel like you're traveling by steamer. Whatever mode of transport you choose, this hardside trunk, with its waterproof, double-deck compartments, makes an elegant companion.

Super Léger Carry-On, $405, tumi.com.

If you like standing out in a crowd, this is the bag for you. Besides the color, the sleek, leather-trimmed nylon will keep you looking sharp while the interior strap will help hold your essentials in place.

Esnoble 20-inch Spinner, $495, hartmann.com.

In the luggage business since 1877, Hartmann takes pride in its classic, sophisticated designs. Leather handles, a spacious interior, and gold finishes take this bag above and beyond, but the real bonus is the built-in TSA lock.

4 Wheel International Carry On, $695, tanthony.com.

The dual compartment case is every carry-on packer's dream (double the organizational possibilities!), and this one is the zenith of the category. The functional design with two extra interior zip pockets and one exterior is the perfect luggage for the ultra-organized.

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