'Historically air travel was a glamorous pursuit, hence the term "jet-set,"' said Valerie Steele, director of the museum at New York's Fashion Institute of Technology.  THE LAST TIME I embarked on a 15-hour Air France flight from Milan to Los Angeles via Paris, I wore a flared, knee-length Mary Katrantzou jacquard dress, Gianvito Rossi heels, a vintage 1950s sweater and enough costume jewelry to set a metal detector off its rocker.  Photo Details: (Clockwise from top left) Burberry Prorsum Animal Print Loafers, $495, Burberry, 212-407-7100; Frends Taylor Rose Gold Headphones, $200, nordstrom.com; Valentino Garavani Pink Rockstud iPad Case, $895, Valentino, 212-772-6969; Concours D'etriers Scarf, $1,125, Hermès, 800-441-4488; Marshall Travel Wallet, $540, Smythson, 212-265-4573; 18K Rose Gold and Amethyst, Pink Quartz and White Quartz Rings, $3,700, $4,800 and $4,000, Pomellato, 800-254-6020; Eddie Borgo Inlaid Bezel Bracelet, $600, Neiman Marcus, 310-550-5900; Charms 32mm Timepiece with Swiss Quartz Movements with Diamond Case and Bracelet set in 18K Rose Gold, price upon request, Van Cleef & Arpels, 877-826-2533; Silver Buckle and Leather Strap Belt, $220 and $370, Hermès, 800-441-4488  The friend who collected me at the end of my journey pulled up to the curb at LAX, raised her eyebrows and said: "You wore a dress on the plane?"  Yes. I always wear a dress on the plane. Or a skirt, ideally in an A-line shape. And heels and jewelry and much more from the A-game side of my closet. The airport check-in staff, security guards and cabin crew, meanwhile, all love me for it. I am frequently granted upgrades, and treated politely by typically aloof Parisian stewardesses who pet my lovely coats before hanging them in the cabin closet. Once, I got high-fives from a group of security girls at Newark airport for the vintage, two-piece patterned knit set I was wearing with a fox fur vest. And though I sometimes garner a few startled looks from fellow travelers in the security line as I pull off my layers of gold necklaces, many also ask where they might find my camel's hair coat (Max Mara) or my glossy ponyskin tote (Givenchy).  “I got high-fives from security girls at Newark airport for the two-piece set I wore with a fur vest.”  At Milan's Linate airport, the security guards are so pleased to see someone who made an effort to look good (naturally, they assume it was intended for them) that when my pointy-toed Nicholas Kirkwood pumps with metal heels set off their detectors, they smile, shrug and wave me through anyway.  In my experience, although the French also appreciate a traveler who has bothered to put herself together, they are sticklers for the rules. When my Kirkwoods trigger the alarm, the guards escort me to a civil place to sit as I remove the shoes. They offer plastic foot wraps so as to not soil my bare soles while I am re-scanned. I have yet to experience this on American soil, which could be one explanation for why everyone seems to show up to U.S. airports in running shoes or plastic shower sandals.  The beach is beckoning, but before you hit the shore, consult this guide to 50 seaside essentials—from swank swimsuits to ice-cold canned sake, comfy snorkel fins to video-recording binoculars.  Sometimes, I'll admit I overdo it. For instance, I do not advise wearing a door-knocker-size necklace on a long-haul flight unless you want to wake up with an imprint of gold-plated leaves on your cheek. But for the most part, my in-flight fashion choices are sound. I can still race to the gate in a pair of 1½-inch block heels. My skirt or dress will not arrive embarrassingly rumpled because I've chosen one cut from a sturdy, wrinkle-resistant fabric. And to ensure warmth at lofty altitudes, I add thick, black, opaque tights.  A thoughtful travel ensemble has not always been the exception. "Historically air travel was a glamorous pursuit, hence the term 'jet-set,' " said Valerie Steele, director of the museum at New York's Fashion Institute of Technology. "People dressed up in nice clothes, hats and gloves. Unfortunately, as air travel became a mass phenomenon, it became considerably less luxurious."  HOW TO UPGRADE | A full-skirted dress can be more comfortable than jeans. Just add thick tights for warmth after takeoff. Above: Grace Kelly, Elizabeth Taylor and Laraine Day in 1954.  Indeed, many travelers view going to the airport as a short-term prison sentence with a series of indignities that includes invasive bag searches and waiting like livestock in lines before being freeze-dried into a seat with only two inches of leg room.  Coordinate accessories to look polished. Leave the messy, mismatched bags at home. Sophia Loren, circa 1965.  If over-the-top isn't your thing, simplicity—a dark skirt and cardigan with a pale blouse—still wins. (Over-the-knee boots optional.) Brigitte Bardot, 1968.  "It's difficult to expect people to dress up for that kind of experience," Ms. Steele said.  A beautiful jacket or coat can make an ensemble—and keep you toasty. Barbra Streisand, 1975.  But I do it anyway. Why? First, it's a myth that good-looking clothing has to be a torture chamber. There are plenty of presentable—even very chic—options that are comfortable. Second, dressing well improves morale. It offers what Ms. Steele called, "a psychological boost."  Jeans aren't entirely out of the question, certainly not if they're paired with a tailored jacket, silk scarf and fedora. Diane Kruger, 2010.  Thankfully I'm not alone in my thinking. "At the very least [dressing up] is a benefit for your self-esteem," said Ginevra Elkann, president of the Pinacoteca Giovanni e Marella Agnelli art museum in Turin, and a mother of two. When flying, Ms. Elkann relies on polished outfits like a pair of wide-legged, compact-wool crepe trousers, a starched shirt, a cashmere sweater, ballet flats and an oversize Hermès Birkin bag. "Not a track suit, and never jeans," said Ms. Elkann, whose grandfather Gianni Agnelli, former head of Fiat, was a pillar of impeccable Italian style. "It's the idea of being composed but comfortable."  Stephanie von Watzdorf, the New York-based fashion designer behind the label Figue, flies in silk, men's-style Isabel Marant shirts, jewel-embroidered jackets from her own label, slipper-like flats and at least two bright pashmina scarves. She is nostalgic for the jet-set days. "When I look around I don't understand what's happening," she said. "It's a mess. People are so badly dressed."  "This whole infiltration of the sportswear world has made a huge impact on how people are dressing," explained Justin O'Shea, the buying director for online luxury retailer MyTheresa, who flies frequently for work. But there's a right way and a wrong way to wear rubber soles. "When a woman puts wide Céline pants with sneakers, it's chic," he said. "When they're with a neon pink Juicy Couture track suit, it's weird." Like Ms. Elkann, he advocates the masculine-influenced looks that designers have been showing for the past couple of seasons as an ideal travel-day aesthetic. "It's that crisp, button-down shirt with tailored pants thing," he said. "It's very cool and easy." It's also a look that doesn't need to be expensive.  Another reason I prefer my flights of fancy is sheer originality. "Honestly, it just feels subversive to dress up since no one else is," said Jay Lohmann, a painter who has studios in both Milan and New York and travels frequently between the two. He flies in a pressed shirt, jacket, tailored pants and Moreschi boots. "By the way, I get upgraded all the time," he added. On a recent flight from London to Milan, Tank magazine publisher Caroline Issa wore a huge fuchsia Preen skirt, a baby-pink A.W.A.K.E. jacket and a shock of red lipstick. "In a sea of businessmen in black, I was a bit of a flamingo," Ms. Issa said with a laugh. "I love to stand out."  Mile-high chic doesn't require mile-high heels, but choose flats with panache. Sarah Jessica Parker, 2012  Though my own plane looks may be a bit over-the-top, a survey of some very chic women proves that mile-high style can also be relatively low-key and low-maintenance. Susanne Thun, who works with her husband, architect and designer Matteo Thun, only wears flats, preferably tiger-print Roger Vivier ballerinas, along with neat jeans or trousers and cashmere sweaters for traveling to and from St. Moritz, Milan, Vienna and Capri. She gives a twist to her simple style by layering shades of cream, camel or navy in a monochrome look. Ms. Issa occasionally wears cashmere sweatpants from Canadian sports apparel brand Roots. She said their high waist and side pockets make them appear to be tailored trousers.  For those who are pressed for time, a great jacket or coat can very quickly neaten up a sloppy or casual ensemble—and keep a passenger warm. Noona Smith-Petersen, a publicist in Milan, relies on stiff overcoats and tuxedo jackets from Céline; their rigorous lines and wrinkle-proof fabrics can transform casual white jeans and Church's lace-up oxfords (or even her Converse sneakers) into a high-end look. "I could never go to the airport looking sloppy," said Ms. Smith-Petersen. "[Flying] is like going to a restaurant. It's like going out."  Max Mara brand ambassador Nicola Maramotti grabs the company's down-filled Cube puffer jacket, which is reversible, convertible (you can dress it up with a fur collar and cuffs) and collapses down into a compact cube shape with a handle. "I always want to feel comfortable and elegant," said Ms. Maramotti, who often leaves the company's home base in Reggio Emilia, Italy, for London, New York and Los Angeles. "I don't understand people dressing as if they're going to the gym."  To be honest, I'd probably dress for the gym if everyone else were wearing digital-print dresses and kitten heels. But as long as the masses continue to fly in Pilates pants and running shoes, I'll be stepping through security looking cocktail-party ready.  A version of this article appeared June 15, 2013, on page D1 in the U.S. edition of The Wall Street Journal, with the headline: An Argument for FlyinginHighStyle.
The golden age of air travel may be over, but that's no reason to dress like it is.