Carry-on Rules for Rookies — The Remarkable Explorers Club

Last year, I had a bet going with myself to see how rarely I could check a suitcase. Of the two times I failed to carry on, my bag got lost once, cementing my belief that, whenever possible, it’s best to travel light.

This challenge has really brought out my competitive streak. Four days at Sundance Film Festival with enough gear to ski all day and DJ each night? No problem. Two weeks in Tuscany with a Bacchus costume, complete with vine crown, for an arty summer fete? Easy. A Missoni butterfly pool float requested by my friend for his five day party in a chateau outside of Biarritz? Uh… Sure.

Along the road I have developed a strategy to keep the packing process as streamlined as possible. Since summer clothes are lighter, why not give it a try while the weather’s warm?

RULE #1: Packing starts when you shop.

Despite being a good packer I am by no means a minimalist. In order to fit more into less space, I have made a point of buying lighter fabrics. Anything fussy, requiring an iron or a Tide pen (I’m basically allergic to white), stays at home. Instead, I opt for lightweight pieces that can be worn day to night, dressed up with a big pair of earrings or a bold lip. It seems to be the summer of the slip dress, and this doesn’t feel like a coincidence.

RULE #2: Your carry on should be the maximum size in the allowance window.

This can obviously get you into trouble if you’re hopping around Europe on budget carriers, but I travel with the two largest pieces my airline will allow. People often underestimate the capacity of the personal item, but this Paravel weekender paired with a Rimowa cabin case doesn’t end up feeling much smaller than a checked bag. I also recommend packing cubes to keep everything organized.

P.S. I always buy higher end luggage pieces in Europe as the prices are better and the warranties apply internationally.

RULE #3: Decide WHO the star of your wardrobe is (AND let the rest be supporting cast).

Some travelers dig jeans with colorful sneakers or heels. I don’t believe in wearing pants April - October if it can be avoided. Because most of my dresses are colorful or printed, I go more neutral for accessories. Usually I pack two color stories and make sure I have coordinating shoes, purse, and sunglasses for both. That could be black, brown, nude, or metallic, depending on what I’m bringing. If there’s another star piece or two I want to throw in, at least I know I’ve covered my bases. Also, one pair of heels max for me. They take up too much space and I’m already a giant.

RULE #4: Anything that needs to be pulled out for security goes in your personal item.

This means laptops, cameras, occasionally hair tools and, depending on which airports you’re passing through, toiletries. Certain airports (ahem, Heathrow) really crack down on liquids. So, to save yourself time, have these pre-packed in a clear bag that you can throw in a scanner bin with your electronics. Shoes that zip or slide off easily are also a great move. Who has time for laces?

RULE #5: Wear your bulkiest PIECES on the plane.

For summer travel, I’ll pack a denim jacket and wear either a blazer or something a little jazzier (depending on my itinerary) on the plane. This white fringed Stella McCartney jacket goes with absolutely everything, and absolutely nothing, so it will probably take the flight to Nice with me later this month. If I’m bringing a little rocker bootie or a bulkier shoe, I’ll wear those onboard as well. I’ll also toss a small purse or pouch with all my in-flight necessities at the top of my personal item so these are easy to access in flight.

…and if you’re feeling ambitious, don’t forget the pool float.