Traveling in comfort and style

Photographs by Bob Rozycki

There’s a terrific moment in “Pride and Prejudice” – not the one with Keira Knightley but the definitive version with Colin Firth as Mr. Darcy – where Maria Lucas (sister of Charlotte, who’s the BFF of Elizabeth “Lizzie” Bennet and wife of the fatuous Mr. Collins, whom Lizzie has rejected even though he’s going to inherit the Bennet estate, which has been entailed away from the female line) packs and repacks her trunk, because she fears it is not up to the Olympian standards of the imperious Lady Catherine de Bourgh, Mr. Darcy’s aunt and Lizzie’s nemesis. Whereupon the self-possessed Lizzie informs Maria (pronounced Mah-RYE-ah) that since it’s her trunk and her dresses, she should pack anyway she wants and no one will ever know.

Way to go, Lizzie. Still, you sympathize with Maria. You plan the perfect vacation. You have your mode of transportation and lodging all lined up. And then you’re almost done in before you even depart by the daunting challenge of what to wear and how to pack it. It’s why some people hate to travel.

We know the feeling. That’s why we asked style gurus and WAG alumnae “Diva” Debbi O’Shea and Kendra Charisse Porter for some tips to help us put our best (sandaled) foot forward:

1. Travel light. As the child of an over-packing mother, Kendra never checks luggage and went all the way to Mexico for a cousin’s wedding with just a carry-on and a book bag. Debbi, too, says, “I’ve given myself permission to repeat outfits. You want to look chic, but you’re not going to be able to take everything with you.” With that in mind, what you wear on travel day is important, because it sets the tone and foundation of your vacation wardrobe. “There are no orphan pieces,” Debbi says.

2. Layer your travel-day look. Debbi likes a light cashmere tank, long jersey cardigan, Ali Ro skinny jeans in a color other than the traditional blue, a lightweight microfiber raincoat that rolls up, a medium-size purse and sturdy Yosi Samra packable flats in a neutral color. Kendra likes to wear the bulkier items that would take up space in her suitcase, traveling in jeans, sneakers, a tank, a button-down shirt, sweater and jeans jacket. (Obviously, the number of layers you wear will depend on the season and destination.) Key for both women – a big scarf that ties the outfit together and can serve as a cover-up, shawl or blanket.

For the guys, the stylists say, same idea. Debbi says a man can’t go wrong in dark-blue boot-cut jeans, a polo shirt, a good-looking travel shoe, a nice belt, a Zegna microfiber zip fleece pullover and a lightweight jacket. Kendra adds that light sports, track or cargo jackets are all good options for them.

3. The carry-on is all that stands between you and disaster. Veterans of the Lost or Misdirected Luggage Wars, Debbi and Kendra swear by their carry-ons. Debbi even recently treated herself to a woven hemp tote with leather trim by Fairchild Baldwin. In general, your carry-on should always contain your valuables and necessities should your checked bag be delayed – jewelry in a jewelry bag, electronics and chargers, overnight toiletries and makeup in TSA-appropriate bottles (look for sample sizes), medication in a multiday pill container you can find in any discount drugstore, a change of underwear and top, nightwear and socks to keep the tootsies warm, dry and clean in any environment.

4. Try the pyramid approach to packing. Having selected a palette of no more than four colors – say white, taupe, navy and black – Debbi and Kendra pack from the heaviest items to the lightest but in different ways.

Debbi, who is checking her suitcase, begins with her beach bag, umbrella and toiletries, contained in those heavy zippered bags that sheets come in, on the bottom. Next go her beige wedge sandals and pewter flat Jack Rogers sandals in cloth sacks. Then in go two pairs of shorts – one white, one bright; three bathing suits; one Calypso St. Barth cover-up; one pair of white jeans; one cardigan (white or taupe); two tanks; two Ts; one V-neck long-sleeve sweater; two pairs of yoga pants; two exercise tops; a neutral clutch; three jersey dresses on one hanger in a dry-cleaning bag; two oversize scarves; two nightgowns in different weights; and a packable hat with tissue in the crown. (No, we didn’t forget the undies. They line the sides of the suitcase.)

Kendra, who is using her carry-on as her suitcase, favors unlined, washable linen pants in white and taupe, corresponding blouses, a linen jacket, sundresses, a nightgown, two bathing suits (in ziplock bags) and a cover-up that can be transformed into a dress, top or towel. To these, Kendra takes the military-style approach, folding and rolling each article. She places her toiletries on the top or side of the bag in a clear cosmetic case so airport security doesn’t have to hunt for them. But doesn’t linen wrinkle? “It will have creases anyway,” Kendra says. “Besides, I’m OK with a little ironing.”

5. And for the guys: Kendra and Debbi favor a pair of dress shoes and something they can be comfortable in – mules, good-looking leather sandals, water shoes; a couple of pairs of shorts; a bathing suit; well-fitting khakis (try olive green and navy, Kendra says); chinos; cargo, convertible or running pants; a dress shirt; some polos and Ts; and a blazer in a garment bag on top.

And don’t forget a tie, guys. You never know what fancy place we’ll wind up in.

For more on Debbi O’Shea, visit For more on Kendra Charisse Porter, visit

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