Chic Travel Picks and Packing Secrets To Avoid The Next Southwest Fiasco

Packing efficiently is a bit of an art form, but for those who know how to do it, it’s a game changer.
Tina Ray

It’s been said that waiting for your luggage to arrive on a baggage carousel adds about a hundred and twenty-seven minutes to any flight. Ok so we made that up, but it sure can feel like it.

Packing efficiently is a bit of an art form, but for those who know how to do it, it’s a game changer. What do those who travel with carry-ons know that you don’t? Traveling with less stuff saves you time in every way imaginable—less time packing and unpacking, less time deciding what to wear, less time at the chiropractor fixing the damage for all that schlepping, and less time worrying if you'll encounter the next Southwest lost baggage fiasco.

Who better to give us a packing tutorial than a former flight attendant who’s logged hundreds of thousands of air miles in her more than 15-year career? Yup, Tina Ray is an expert. “I learned quickly how to pack everything I needed for 4 to 7 days in carry-on bags,” she says. “There was no other option.” Ray’s advice? Choose shoes wisely, prepare to wear (and re-wear) your clothes, maximize for versatility, and find a killer travel bag. Let’s break it down.

Cut back—way back—on shoes.

Wear one pair, and pack two. Full stop. Those satin strap feathery heels? You don’t need them. Ditto for the boots you JUST bought (never bring brand new shoes on a trip). “I realize that this limitation may be difficult for some,” Ray says. “But keep in mind that shoes are the heaviest and bulkiest items you’ll pack.”

Think of it this way: Each pair of shoes takes the space and weight of about three pieces of clothing. You do the math.

The shoes you bring should work for the weather, the dress code, and foremost your comfort. “There’s nothing worse than having your feet hurt while running through the airport or being uncomfortable during that inevitable foot swell while in the air,” Ray reminds us.

Tina’s Tips:

  • #1: Use shoe bags to pack your shoes. Keeping your shoes covered will help them to last longer.
  • #2: Pack your shoes along the side of your bag instead of putting them in the middle of your bag. You’ll have more room for your clothing in the middle of the bag.
  • #3: If you need heavy boots on your trip, wear them while you travel so that the bulky boots don’t take up so much room in your bag.
Nike DBreak SE
Birdies The Swift
Cole Haan Cloudfeel Knotted Espadrille Loafer
Rothy’s The Driver
Patricia Green Jillian Loafer
Rag & Bone Rover Pleated Suede High Ankle Boots

Pack once, wear twice.

Everything in your bag should do double, even triple, duty. Think of styles that have versatility, that can be worn over (or under) other items so that you can layer them and wear them in different ways.

A mid-weight layer - cardigan, knit blazer, or utility jacket - is a perfect example of versatility: it can be worn over a button-down OR a lace camisole, under a coat, or on its own. “Layering pieces are a must when traveling. Who isn’t cold on airplanes?! Also, a lightweight sweater or jacket is a core travel item for when the temperatures drop at night,” Ray says.

Tina’s Tips:

  • #1: Because of the bulk, wear one of your layering pieces on the plane and pack one, giving you more room in your suitcase.
  • #2: Choose versatile pieces that can be dressed up and down - a blazer can be layered over a comfy sweater on the plane and over a midi dress on a night out.
  • #3: A limited color scheme is important so that everything can go with everything. Pick a tone and stick with it. “You get better at it the more you do it,” Ray says.
Caslon Open Front Cardigan
Michael Stars Alec Twill Utility Jacket
Liverpool Los Angeles Open Front Boyfriend Blazer
Nic + Zoe Mosaic Mix Knit Blazer
White House Black Market Military Style Topper Jacker
L’AGENCE Lacey Knit Blazer

Pack one great dress.

It’s hard to beat the ease of a dress, especially when you’re traveling—you don’t have to think about what goes with what and if you choose a comfortable fabric and style, it can be as wearable as a pair of sweats on the plane. “I love traveling in dresses because you can throw on a layered cardigan and some simple jewelry, and you’ll be ready to go anywhere once you arrive at your destination.”

Karen KaneArtisan Jersey Midi Dress
Pomander Place Gio Maxi Dress
Anthropologie Maeve Tiered Shirt Dress
Anthropologie Maeve Printed Shirt Dress
Frank & Eileen Rory Maxi Shirt Dress
Alemais Marion Belted Printed Linen Midi Shirt Dress

Edit your everyday bag.

Whatever you’ve shoved in your bag over the last few weeks—two pairs of extra sunglasses, three pairs of extra reading glasses (that’s why you can never find them!), five tubes of lipstick in indistinguishable shades of mauve, that broken door hinge that you’re trying to replace…you don’t need to take it with you on a trip.

Go through your bag and edit. While we’re at it, find yourself a bag that you designate for travel: it should be lightweight and roomy, work with multiple color schemes, include functional pockets, and, if possible, have the optionality to be worn crossbody.

Vince Camuto Mekhi Large Crossbody Bag
Calvin Klein Crisell Magnetic Logo Crossbody Bag
Cole Haan Grand Ambition Small Convertible Backpack
Troubadour Featherweight Tote
MZ Wallace Black Crosby Daily Tote
Tina Ray

Tina is a former flight attendant turned stylist. She works with busy moms - like herself - to define their personal style and dress in ways that positively impact how they feel every day. Oh, and travel packing tips? She’s your woman.

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