Foolproof Travel Outfits

Annie Fitzsimmons, <a href="" target="_blank">National Geographic’s urban insider</a>
Annie Fitzsimmons, National Geographic’s urban insider

I am typically on the road two weeks every month—sometimes more, depending on the season. When traveling, I usually wear skinny black jeans and two layers—either tissue-thin long-sleeve T-shirts or a tank top and a cardigan. I’ll wear black boots in the winter and comfortable sandals in the summer. I alternate between a LoveQuotes scarf and an oversize black wrap I’ve had forever.

For luggage, I use a purple carry-on Lipault bag and my beloved black O.G. Lo & Sons bag, which fits all of my electronics and trashy magazines.

You can follow Annie on Twitter at @anniefitz.

Peter Corbett, CEO of iStrategyLabs
Peter Corbett, CEO of iStrategyLabs

I’m the CEO of a fast-growing digital agency with clients all over the world, so travel is just a part of breathing for me these days. In the course of a year I visit about 20 or 30 cities, travel roughly 200,000 miles, and spend four or five months on the road.

My go-to travel setup is a backpack stuffed with a laptop/iPad/magazine, and a roll-aboard. Never check a bag. Ever.

My go-to travel outfit is gray Diesel jeans, easy-to-slip-off Pumas, a T-shirt, and a black Puma Ferrari zip-up hoodie.

You can follow Peter on Twitter at @Corbett3000.

Lee Woodruff, author, mother, and cofounder of <a href="" target="blank"> Bob Woodruff Foundation</a>
Lee Woodruff, author, mother, and cofounder of Bob Woodruff Foundation

I travel all the time as a speaker, author, and journalist. I love my red Diesel bag—I got it for $77 after my black Tumi bag handle broke and two men tried to wheel away with my carry-on. I decided to buy a bag that most men would be darned sure was not theirs!

I never check luggage, and I keep my to-go bag packed with medicine in a Ziploc, makeup in a Ziploc, La Mer face cream, my swimming goggles, cap, and suit, cards I hand out at book signings, the same jewelry (tiny costume diamond hoops), a razor, a comb, and PJs.

I usually fly with some form of yoga pants so I don’t end up in jeans with my crotch cut off from blood flow on longer flights.

I have a navy Tumi computer bag that serves as my purse and computer carrier and holds EVERYTHING: throat-coat tea, eye cream, pens, Kleenex, a comb, a toothbrush, hand cream, mascara, lip gloss, and foundation for in a pinch, and a glass Voss bottle of water that I reuse.

You can follow Lee on Twitter at @leemwoodruff.

Janine Cifelli, Janine Cifelli Representation
Janine Cifelli, Janine Cifelli Representation

I’m the CEO of Janine Cifelli Representation, a hotel representation firm specializing in hotel and resort marketing, so I’m on the road constantly—a week or two a month—and many of the trips are international.

My travel style is a long cardigan that covers the tush over skinny pants, with a tank under and possibly a long-sleeve shirt, as well. It’s always cold on the plane!

I put pants with stretch and a pair of leggings in the carry-on if it’s an overnight flight, as I always change. Also my pashmina and comfy flats.

In my carry-on I have a comfy neck pillow, socks, Advil, melatonin, Ambien, a phone charger, an eye mask, earplugs, and my iPad.

You can follow Janine on Twitter @JanineCifelli.

Andy Ellwood, senior director of business development, <a href="" target="blank">Waze</a>
Andy Ellwood, senior director of business development, Waze

My go-to travel ensemble is an Eton of Sweden button-down shirt, a sport coat, a pocket square, Levi’s, and cowboy boots.

I wear the Eton of Sweden shirts for stepping up beyond the normal blue-and-white button-down of all other business travelers, and a sport coat with a good interior pocket to keep my airline ticket so I don’t have to fish around in my bag before going through security.

Pocket squares get you smiles from the TSA, better service from the gateside restaurant, and upgrades if you ask nicely.

Levi’s jeans, because the Waterless jeans are impact-worthy and a step above Steve Jobs dad jeans but not so far up the denim food chain that people assume you’re a jerk.

Cowboy boots, because it completes the cowboy tuxedo and they’re easy to slip off at security.

You can follow Andy on Twitter at @andyellwood and check in with his pocket square at:

Barbara DeLollis, founding editor of <em>USA Today’s</em> Hotel Check-in Blog
Barbara DeLollis, founding editor of USA Today’s Hotel Check-in Blog

I’ve traveled to Montreal, Miami, Los Angeles, New York, and Barcelona in the past six months. My go-to travel outfit depends on where I’m going, but style is almost always paramount to comfort.

When heading to warmer tourist/beach destinations, I usually pick a dress that doesn’t wrinkle, along with sandals that will let me run through the airport to catch my flight if need be. I’ll typically add an accessory that won’t trip up the TSA but that adds some sparkle to a possibly mundane look, such as the belt in the photo. Since I always get cold on planes, I throw on a black blazer and toss a scarf in my bag. I keep jewelry to a minimum, again to reduce hassles at the security checkpoint.

When heading to cooler climates and/or big cities, I grab my other “uniform”: a pair of designer jeans, a comfy T-shirt, a blazer, and boots. For some inexplicable reason, I usually opt for heels, even if it means I’ll have to run in them in the airport. Most of the heels I buy are comfortable anyway, so it’s not a big deal. When I’m heading to cities, it also means I’m likely going to be in a mad dash the entire time and won’t have time to waste stopping to change out of boring travel attire.

Regardless of what I’m wearing, I typically use my favorite dark leather bag and the gray roller suitcase my dad gave me; it’s nothing fancy, but it makes me think of him! The only time I check luggage is when I’m heading to Virtuoso Travel Mart in Las Vegas. This conference is heavily attended by fashionistas, so if you want to even attempt to join in on the fun, you need to pack different outfits for day and night for five consecutive days!

You can follow Barbara on Twitter at @barbdelollis.

Erina Pindar, director at <a href="" target="blank">SmartFlyer</a>
Erina Pindar, director at SmartFlyer

As a director at a very busy travel agency, I’m on a plane at least once a month for work and have been to six countries so far in 2013.

My go-to outfit is black American Apparel leggings (because they make thicker leggings!) with the perfect white V-neck tee (Isabel Marant and Everlane), a black Loro Piana cashmere scarf, and nude flats.

My favorite carry-on is the Longchamp extendable Le Pliage bag. You can follow Erina on Twitter at @MissSmartFlyer.

Andrea Fellman, founder of Savvy Sassy Moms
Andrea Fellman, founder of Savvy Sassy Moms

My typical travel outfit is skinny jeans, ballet flats, and a scarf. I typically get cold on flights, so I usually dress in layers: a long-sleeve shirt, cardigan, or light jacket. If I am staying more than two days and think I’ll get in a workout or if it’s a long flight, I’ll dress in an athletic outfit and wear my tennis shoes. They take up so much room in a carry-on, so it’s better to wear them on the plane to save space—but only if you are not going directly to a meeting or event.

A large carry-on bag will carry not just your wallet and laptop but also any extra accessories, toiletries, and even an extra pair of flats. A large enough carry-on will also hold a nighttime clutch that you can fill with jewelry or all your electronic charging cords to maximize space.

Tieks are my go-to travel flat because they are high-quality and are actually great for a lot of walking. They also fold up very small and will fit into just about any handbag. You can follow Andrea on Twitter at @andreafellman.

Stacy Small, president of Elite Travel International
Stacy Small, president of Elite Travel International

As the president of a luxury travel firm, I travel a lot! In a month I’ll be onboard nine different planes, visiting nine different cities in four different countries, and will be away from home two out of four weeks.

My go-to outfit (styled by @SheltonWilder) typically includes stretchy black Theory pants and either comfy black leather boots from Barneys or Cole Haan/Nike Air flats, depending on my destination. I pair those with a colorful Michael Stars or DVF top so when I land I don’t look like a complete zombie, topped off by an long, oversize black Vince sweater that basically doubles as a blanket in-flight.

I always try to limit my carry-on luggage to my Briggs & Riley rolling computer bag—which is roomy enough to fit my laptop, my iPad, jewelry, gluten-free snacks, and a few work files, but compact enough not to take up too much space—along with a medium Marc Jacobs or Ferragamo handbag that easily fits my phone (iPhone and BlackBerry), wallet, and a few random toiletries such as refresh eye drops and regenerating cream from Rhonda Allison. You can follow Stacy on Twitter at @elitetravelgal.

Amie O’Shaughnessy, founder of Ciao Bambino
Amie O’Shaughnessy, founder of Ciao Bambino

Balancing fashion and function is key for long-haul flights. Avoid jeans, as they do not breathe and they stick to seats. Soft khakis are a year-round favorite, with a cozy long-sleeve T-shirt (James Perse is a fave for this) and a light sweater or Patagonia fuzzy thrown around my waist, depending on whether my final destination is urban or rural.

Whatever is right next to my body for all those hours is one-and-done, so it needs to be compact and disappear into my suitcase. I wear whatever shoes are comfortable but bulky and take up precious suitcase real estate. Use jewelry or scarves to give simple layers flair. You can follow Amie on Twitter @CiaoBambino.


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