When my girlfriend Judy half-joked “I don’t know, maybe that’s what broke up my marriage…” the that to which she was referring wasn’t any of the usual suspects like money, infidelity or the gradual growing apart which can cause couples to say “I don’t.” Instead, it was her baggage. Or, to be more precise, her excess baggage.
“Bag lady you gone hurt your back
Dragging all them bags like that
I guess nobody ever told you
All you must hold on to
Is you
Is you
Is you
-Erykah Badu
Photography Courtesy of Gilles Bensimon

When I think of Judy two things invariably come to mind: air and light. Which is why it came as a shock to learn that she was a Bag Lady. And I’m talking hard core. As in the time she hauled eight pieces of luggage to Prague and Budapest on a ten-day getaway and wound up having to ship her Duty Free purchases home because there wasn’t enough room in any of her (did I mention, eight?!) bags to get the job done.
To be fair, Judy comes by her predilections honestly. An executive in the beauty business, her appearance is her calling card and in order to succeed she has to look the part at all times. Judy’s pretty face and statuesque frame were a gift from the genetic lottery, but even she can’t roll out of bed looking like the One Percenter from the Fortune 100 Club that she is without a little help from the hair, makeup, wardrobe and accessories department. And while she is as adept at pulling together a look that conveys “I got this” in business as she is at contract negotiations & client relations; the very assets which have bolstered Judy’s success in Gotham become a liability when she takes her show on the road.
If we are lucky enough to travel for leisure, we can do one of two things when determining what to wear while away from home: dress to impress or seek to be impressed by the places we visit. It goes without saying that the former has its charms. But unless one is Lady Mary from Downton Abby traveling with one’s personal butler, valet (non-silent “T”, thank you veddy much), maid and footman to unpack one’s steamer trunks upon arrival– it might be more prudent to pack light and enjoy the ride.
Make no mistake, I am not saying a lady should morph into a frumposaurus just because she is on vacation. But she should be ready to get-up-and-go without being a drag on her travel companions… or poor, unsuspecting husband who finds himself schlepping her bags and mentally Czeching out.
To wit: my two-cents on putting your best foot forward without packing 12 pairs of shoes and a blow dryer.  
Photography Courtesy of Naina Williams

As it happens, the feet are an excellent place to start! 
I once knew an art director at a fashion magazine who would reject an otherwise perfect photograph for publication if the model’s nails looked unkempt. Naturally, he was a Frenchman. And he was right. What he taught me was that the most powerful tool in any woman’s arsenal is her polish –in the literal and figurative sense. So while I’d encourage you to leave home without the Jimmy Choo’s in order to conserve space, I would also insist that you treat yourself to a manicure and pedicure before taking flight. Then flaunt your pretty feet in one or two pairs of flat sandals that can carry you from day to night without taking up too much room in your carry-on bag.
Of course, there is no more effective buzz kill than corns and hammer toes on display for all the world to see. So consider covering up if your feet aren’t going to take any Best in Show prizes in 2012. And try to remember that the best way to minimize any further wear & tear on your tootsies is by wearing shoes with good support that don’t impede your stride. Nikes are so perfectly suited for the job that they’ve become synonymous with the American tourist. But why make the cobblestones cringe as you trip the light fantastic through Dubrovnik in what look like marshmallows for the feet when far more elegant solutions abound?
Trainers like the Thoung Dihn from Vietnam (http://www.thuongdinh.com/), pictured below, are appropriate whether you find yourself in town or country… dressed up or down… running through an airport or on a treadmill at your hotel gym (though why anyone would do this to themselves while on vacation is a mystery to me). Sneakers like these also collapse easily for packing– helping you stick to your new one bag policy when traveling.

Yes, Judy. I said one bag and I am talking to you!

The images above and below are my two all-time favorite vacation snapshots. Up top are my Aunt Frances and Aunt Barbara– likely enjoying a day on Lake Michigan in the 60’s. And that’s my sister Dee Dee looking like a Prada-esque wood nymph on holiday in Ibiza last spring. What all three women have in common is the way they’ve cleverly deployed a simple scarf to boost their individual style-quotients exponentially. 
Photography Courtesy of Michel Malausséna
Equal parts practical and frivolous: scarves are my favorite way to add color to a neutral wardrobe, feminize boyish tailoring and make a bad hair day better. The longer & lighter the better because then your scarf can actually flutter in the wind.  And what could be more girly than that?! Scarves are also a godsend when confronted with one of those those sketchy looking chairs you’d really prefer not to sit in while wearing a short dress or shorts  on vacation. I always have an extra one on hand for this purpose exclusively, and can’t tell you how grateful other women have been when I loan them my scarf to for this very purpose. Whatever the case, scarves offer maximum impact with minimum space requirements to comply with those pesky FAA regulations for in-flight luggage.
Sense a theme here?
Good, because that brings me the third rail of travel for women: hair… and what to pack when you feel pressed to look salon-perfect. Black women, and any of my sisters with so-called “unruly” hair, you know I’m talking to you so listen up!
 We all know how much physical and psychic space is sucked up when traveling with blow dryers, curling irons, rollers, gels, hairsprays and whatever other contraptions needed to keep our tresses bouncin’ and behavin’, but can we just give ourselves a break from that twisted routine while we are on vacation? In the first place, your already stressed out hair could use the reprieve from all that heat and product. And, secondly, is there anything more fetching than a woman who holds her head high even if every hair is not in place? 
As I see it, vacation hair is to the great outdoors what bed hair is to the boudoir: sexy and underrated. So why not rock yours the next time you take off and see what happens? Best case, you will fall in love with what your mama gave you. Worst case, you can use your trusty scarf to cover up… then curse me out when you come home. But my guess is that something bigger will happen as you cross paths with other women on their journeys who will admire your vacation hair and think to themselves “Next time I think I’ll have what she’s having.”
Photography Courtesy of Maria Trice-Jones
As you’ve gathered by now, it is impossible to change ingrained habits without changing our minds first. I could go on an on about the benefits of the one-bag rule while, but Judy put it best when she described her way of doing things as “burdensome.” She was inspired to change her ways when I sent her this picture of my week’s wardrobe for Florida– where I’m spending time with my family.
I swear on my mother’s head that every item pictured below fit in this one messenger bag. A bag, by the way, which did double duty as my daytime carryall from Key West to Coral Springs. All of the garments were rolled as opposed to folded– an old flight attendant’s trick– which really maximizes space. 
The cream colored J. Crew “City Fit” pants (I loooove them for feeling comfy without looking slouchy), white denim leggings, cuffed shorts (in white and gray) and navy stretch skirt covered my bottom half nicely, while fitted tees with 3/4 sleeves (in pale, navy & cerulean blue) took care of my top half whether dressed up or down by day or night. The green floral print tunic was worn solo as a dress, or paired with the white leggings for more coverage. The same for the fuchsia sundress. And the striped tee worked with every bottom pictured.The other essentials were my flip flops, toiletries in the dreaded clear Ziploc bag, laptop, iPad, chargers, comb, wallet, hand lotion, lip balm, and crocheted purse stuffed with a 7-day supply of Hanky Pankys. If you look closely you’ll notice a pair of yoga pants just beneath the sundress– which were paired with my tees (after wearing them once) to eliminate the need to pack gym tees for early morning bike rides with my mother. I wore white jeans, a plaid cotton shirts and trainers on the plane, with my beloved kikoy (a traditional woven cotton scarf from Kenya http://www.kikoyshop.com/collections/regular-kikoys) wrapped around my neck to stave off the air conditioning in the airport terminal and aboard my flight.
My family is laid back, so I didn’t bring any heels with me on this trip. But had I chosen to,  it would have been a neutral strappy sandal that would disappear on my foot, thereby elongating my legs while coordinating with any of my neutral outfits.
I admit that I’m an extreme packer when it comes to streamlining, but there has never been a time that I found myself sartorially challenged while away from home. The trick is to make decisions at the outset (“I refuse to be a slave to fashion” would be a damn good start, followed by “If it don’t fit, I don’t need it.”) and then stick to them.
My sage advice and packing tips aside, the one thing I want Judy to remember next time she packs a bag is that everything she needs to have the perfect vacation is already within, so “All you must hold on to is you, is you, is you“… just like Erykah sang and Gabby Douglas showed all of us in London.
Illustration Courtesy of Alvaro www.alvaroartz.com
Failing that, Judy, just make the #1 Rule of water skiing your default setting when packing:
“Let go or be dragged.
-Zen Proverb

Bon Voyage!