How to Travel Like Your Private Jet Is in the Shop

Welcome back to Luxury Rules, a life and style column for people of taste who are on a budget. Today, our resident class act, Dodai Stewart, advises you on taking to the sky stylishly, even if you've spent basically all your money on your plane ticket.

The truth is, if you were really and truly wealthy, you’d have a person—either your own, the airport’s, or the record label’s—whose job it was to “take care of the bags,” like a porter, a skycap, a valet, a lady’s maid. Alas! We must persevere without assistance.

Many of you will NOT like this, but my method involves packing light, in a soft-sided bag, which is never so heavy that i can’t lift it, and has NO WHEELS. Checking bags can be expensive, and waiting at baggage claim is an absolute drag. Don’t you want to get off the plane and go? This is not “travel like a flight attendant,” this is “travel like a Hollywood star whose private jet is in the shop!” My brother, who travels commercial when he must, never uses luggage with wheels, saying “When running through an airport I’m usually late and breaking rules of physics, navigating crowds and lines. I don’t like the restrictive nature of wheels. I’m also freaked out by the amount of dirt [wheeled luggage accumulates] as wheels go over sidewalks and subway platforms and then (gasp) onto the bed.” He also notes that if you want to make like a model and take the moto taxi in Paris—perhaps to go get ice cream during a layover?—you definitely can’t bring a wheeled bag.

Yours truly went to Iceland for eight days with two soft-sided bags and had room to bring home souvenirs. My alternate piece is a vintage Gucci soft-sided suitcase found on Etsy for under $200. Just try not to go for the typical black wheely thing that’s indistinguishable from a million others—the paparazzi are watching!

Certainly we wish we all could look as glamorous as Marilyn, Mamie, or Sophia while in the air, but most of the sophistication has evaporated from flying and been replaced by surliness, delays, air rage, and fees. Still: You’ll most likely feel better—and possibly be treated better—if you don’t look slovenly. No stained T-shirts with wacky slogans, no “Juicy”-butt sweatpants, no cut-off denim shorts, please. It’s the miracle of jet travel, not a barbecue.

Oversized sunglasses are a must—and they double as a sleep mask. It helps to wear all one color, like a suit. You’ll just look more put-together! It doesn’t have to be an actual suit; you can fashion a suit out of a pair of stretchy trousers and a blazer or cardigan, or even opt for a tracksuit, which is athleisure without the sloppiness. I like to wear a men’s Puma T7 tracksuit, which I copped after seeing it in so many sharp F. E. Castleberry instagrams, but my dream ensemble would be the one I saw on a chic gray-haired woman of a certain age at JFK waiting for a flight to New Orleans: Exquisite silk top and bottoms from For Restless Sleepers with Gucci Princetown velvet slippers. Comfortable, elegant, reeking of money! The rest of us can only hope to just keep it streamlined. When in doubt, always bet on black.

Planes are notoriously cold, making a wide scarf that can be used a blanket—or rolled into a pillow—a good bet. (Reminder: Never use the blankets provided by the airline!) If you’re going from cold weather to hot, you can use a large, opaque sarong as a scarf/lap throw during the flight and then rock it as a coverup on the beach. When heading to tropical from freezing I also like to wear a crisp shirtdress with leggings underneath, which can be rolled down and off during taxiing to the gate—you arrive ready for the heat. But for cold cold cold, even more fun than a scarf or pashmina? A faux-fur throw you can wrap around yourself in flight and then sport as a Grace Jones–inspired wrap in the terminal. You may think I’m nuts, but just imagine how jealous everyone will be as they shiver in their poop blankets and you’re swaddled in plushness. Pull up to the jetway, baby!

After a long day of navigating New Orleans, taking tea in Tokyo, or visiting relatives in Reno, you’ll be so grateful to slip into pretty PJs. You might sleep in a ratty old T-shirt when you’re in your own home, but when you’re traveling, you need something you won’t be embarrassed to be seen in when you run into your in-laws on the way to the loo, or open the door for the gentleman with room service. Splurge or go budget—and if you’ve got a red eye, you can always just roll up to the terminal in PJ pants. Just think of your matching set as a different interpretation of the suit concept.

You can certainly fly without a stash of chocolate, rich with flavanols and neurotransmitter-soothing sugar and creaminess, but why the hell would you? It’s divine to have a secret stash, since plane food is such a gamble. Plus, the prices they charge at the airport are outrageous. Put your favorite chocolate on your night-before-flight drugstore run shopping list and keep it in your under-seat carry-on. You won’t regret it.

The best way to pretend you’re not on a filthy commercial airline surrounded by wailing kids and shady businessmen with “productive” coughs is to block everything out with some serene sounds. Try Spotify’s Deep Sleep or Rain Sounds—although if a podcast or some 702 works better for you, by all means, go for it. I like droning faux-retro Vaporwave, the not-actually-made-in-the-80s Muzak of my dreams.

Applying for TSA PreCheck (they call it TSA Pre, but no one else does), takes about five minutes, and you can do it online. Then there’s a background check and an appointment to be interviewed in person. It’s beneficial for leaving town because it means speeding through the “special” security line at many airports. If you’re eligible, it’s so worth the $85 for a five-year membership: wait in shorter lines, keep your shoes on, keep your liquids in your bag, maintain a sense of decency. Sure, the government will have your fingerprints, but won’t they anyway, eventually?

Global Entry is helpful when arriving back in the U.S. from far-flung places. You can skip long lines and use a machine to scan your passport and fingerprints, saving tons of time. It costs a hundred bucks for a five-year membership, but if you get Global Entry, you automatically also have TSA PreCheck, so if you truly want to travel like a VIP, you might as well!

Ultimately, if you want to put a little romance, a little glamour, a little magic into traveling, take a tip from the stars of Old Hollywood and try to elevate (heh) your look… And if all else fails, take a couple of valerian root pills before the flight to really smooth out the harsh edges (as long as you ask your doctor if it’s okay first!). Bon voyage!