Pack it Up, Pack it In, Let Me Begin . . .


When planning a vacation (as opposed to everything else in life), I am no procrastinator. Well, of course, except when it comes to packing. Packing totally sucks, unpacking is a million times worse, and all of these new airline charges and regulations don’t make things any more pleasant.

I’m sure I’m not the only one who has sat on the floor at three in the morning before a trip, surrounded by a behemoth pile of clothes that resembles the laundry pile from hell. Totally frustrated by this scenario, I created some guidelines that take all of the guesswork out of the task. Ladies, our biggest challenge is this open-ended phrase: “but I need to have choices!” I know I know, and I’m totally with you, but over-packing (like most things that begin with “over”) is so passé. Here are my tips for being cute, comfortable, low-maintenance, and stress-free.



Tip #1: Feet, Don’t Fail Me Now

“Tourist” is a travel dirty word (none of us want to be associated with fanny-packs, visors, or overly large camera equipment) but there’s nothing wrong with coming to terms with the fact that you are in a new place to see sights, and as such you will be doing a lot of walking. Be smart. It hurts my heart to see tourists hobbling around Fifth Avenue in completely impractical heels because they’re under the impression that everyone in New York dresses like Carrie Bradshaw. Trying too hard is never attractive. Anyone can look good in a nice dress and heels; real style is proven in your ability to pull off casual chic. And it’s totally possible! Here’s a sampling of shoe styles that are comfortable, versatile, and affordable:

TOMS Canvas Classics – at $40 a pair, these shoes are a true steal. Plus, with every pair you buy, TOMS donates a pair to a child in need – looking good and feeling gorgeous! They’ve got really great cushioning so you’ll be able to walk all day without having to apply a single band-aid to your heels. Imagine a cute red pair with a casual a-line black sundress – very Audrey and very effortlessly chic.

Flat Sandals – be they gladiator style or woven, beaded or buckled, flat sandals are a low-maintenance travelers god-send. They’ve got all the comfortability of a flip-flop without . . . well, wearing nasty old flip-flops. I recommend something in a metallic for versatility – they’ll go with just about anything. Plus, they’re still on trend so they’re very easy to find in a slew of price ranges and styles. Something as simple as these styles will go a long way.

Fashion Sneaks – Walking through ruins, a lavender field in France, or *gasp* rain? You might want something with a bit more protection. Try a style from a brand that has a more fashion-forward, feminine line, like Puma’s Black Label or Adidas’ Stella McCartney. For example, these ballet flats are supportive and comfortable, but they won’t cramp your style. Too girly for you? You can’t go wrong with a good old classic pair of low-top Chuck’s.





Tip #2: Clothes-Minded

Oftentimes we’re tempted to pack outfits, but the key to keeping things low-maintenance and all in one reasonably sized bag is mix-and-matchable basics. Luckily this is so, so easy to do in the summer, and you don’t have to spend a lot of money at all. When traveling, it’s best to take things that aren’t fussy or too near and dear to you. Everything mentioned below can be found at cheapo-depot retail stores found in malls all across the country.

Tops – at a store like H&M (or Old Navy, J. Crew, etc.) you can find tees and tanks in a full spectrum of colors, sometimes for under $10 a pop. Get crew neck, v-neck, whatever you want, as long as it’s neat and fitted. Be sure to have your basic black and white, but go for something bold, too. Jeweled tones (think magenta, Kelly green, orange, royal purple, turquoise, etc.) look great on everyone and are the key to creating an easy starting point for putting together a complete look.

Bottoms – ladies, are we over 18? Then I do not recommend wearing shorts in a non-athletic environment. Sorry, that’s just the way it is. If you’ve got slim legs up to your chin, you can probably pull it off, but most of us are not so blessed. Um, also, get off my website, I hate you. Luckily us mortals have some lovely alternatives. A-line skirts are cool, comfortable, and compliment just about any body-type. To avoid looking matronly, look for cuts just above or at the knee, especially since you’re likely to be wearing flats. Another warm-weather staple is a linen pant. A wider-legged white linen pant is so perfectly summery. Get a quality pair and don’t wear black undies. Keep your bottoms in neutral colors so that you’ll be able to swap tops easily and fool everyone into thinking you’ve packed a dozen outfits.

Dress Up – a cute dress instantly creates the illusion of being put together. I’ve seen some perfect jersey-knit cottondresses for under $20 at places like Old Navy and Forever 21 in a-line and maxi cuts. Feel free to go for color, but I love the effortlessness of a black maxi-dress, which happen to be ideal for plane rides, too. These fabrics can be clingy, so again, be sure you’re wearing proper chonies.




Tip #3: Dress to Impress with Access . . . ories

And now finally, accessories: the rabbit in the hat, the disappearing ink, the greatest form of travel-fashion magic trickery. Since you’ve now stocked up on basic pieces, you can really have fun and express yourself in so many ways with accessories. Forget the neutrals: with these pieces be creative and daring . . . just don’t wear them all at the same time!

Scarves – scarves are an instant chic-afyier and aren’t just for winter. In warmer months, go for the lightweight linen and cotton numbers in large squares or oblong shapes for versatility. Look for pretty patterns and subdued colors that will compliment (but not “match”) your bold colored tees and tanks. Wear them around your neck, around your waist like a cummerbund (really! It can work!), or as a headband. I go nuts for them in H&M where they’re about $10 a piece. If you’re traveling to a more conservative part of the world (say, the Middle East, a small country town, or visiting a place of worship) these are great impromptu cover-ups. They’re also perfect for museums, theaters, and restaurants which can be chilly.

Jewelry – as with shoes, metallic jewelry is very versatile, so that’s an easy place to start. In the summer I personally love big, filigreed statement earrings, especially in these gold Middle-Eastern inspired looks. A long stranded necklaceor bangles really pack a punch, too. Leave everything fussy, delicate, expensive, or important at home. You don’t want to spend your time untangling things or worrying about anything being lost. Don’t pack too much, though, because jewelry is  THE perfect souvenir. Forget stupid t-shirts or random tchotkes that are useless: buy locally made and designed jewelry! It’s something unique to the locale and when you wear it back home you’ll always be able to say, “oh this? Oh, I bought it in _____” and sound absolutely fascinating and exotic. My favorites are flea markets and vintage shops, but even something special in a touristy market can seem gorgeous when taken home and out of that context. And trust me: if you see and it and love it, buy it. If it’s something one of a kind, it may not be there if you wait until a few hours later.

Bags – ladies, when you decide to carry a large bag on a vacation, you’re only asking to become a pack mule. “Oh, can you hold my water bottle in there?” “This camera is too small for my pocket, can you carry it?” “I don’t want to be pick-pocketed, can you hold my wallet?” You know, NOT THAT THAT HAS EVER HAPPENED TO ME EVER IN LIFE. Be ye not so accommodating. Luckily, travel-friendly cross-body bags are very much in style at the moment. These styles are  lighter-weight and make for happy backs and shoulders. Get a nice one with room for a thin wallet and your necessities, but don’t invite a collection of crap by carrying around a *gasp* backpack, or anything in which you could carry a baby or a small dog. One handbag and a clutch for evenings should be all you need.

And there you have it. All of this should fit in one medium to large sized suitcase with some inventive packing. Fold, roll (my favorite), squish, squash, and take a very small travel steamer. You’ll be able to mix and match tops, bottoms, and accessories enough so that you’ll never have a repeat outfit in your pictures!

“But Kiki, I have this really gorgeous Pucci dress that I wanted to wear in Rome! Are you telling me I’m not allowed to take it?!” Yes, chances are that you’ll be going to a club or to a nice dinner or to a show while on vacation, particularly in a city. Pack one or two special items (like a fab dress or a pretty top and some sexy heels) but don’t go overboard. Plus, it’s just another excuse to shop should you find yourself needing another dressy something. Bon voyage, bitches.


6 thoughts on “Pack it Up, Pack it In, Let Me Begin . . .

  1. WendyD says:

    I so feel your pain with packing. I HATE it. I actually don’t mind unpacking. For some reason, I can do that the moment I get home and be done with it, but before the trip… I would rather go to bed at 11pm and get up at 4am to pack before the flight rather than do it the night before.

    Fantastic tips. Now if I only had some place to implement them to.

    I have recently become a scarf addict, but you remind me that I need to get some summery ones.

  2. Lisa says:

    I’ve been waiting for this post!
    I cant wear shorts? really? But it gets really hot in New Orleans in the summer?
    Actually I ahve found my shorts wardrobe shrinking every year, and I haven’t been replacing them. LAst year I stocked up on some flowy dresses from target that could be dressed up or even worn as a swimsuit cover up. And linen pants! My saviour! Target has some that are not too bad adn affordable. I bought two pair in every color last year and will stock up again this year, they are fabulous!
    My old navy long sleeve pull overs came in so handy our last trip. Black, white, green and turquoise. Stuffed one in my bag every day and when it got chilly, pulled it out and didn’t have to worry about wrinkles or dragging a jacket/sweater around all day or running back to the hotel to grab a jacket when it cooled off.

    I’m in love with scarves too, have a gazillion of them right now, and again, how handy to cover up my neck and shoulders when the sun started getting to be too much and I could feel the burn starting!

    You are brilliant. When I grow up I want to be like you. 😉

  3. Kealan Casey says:

    Haha, I meant to mention you in this post, Lisa!

    And I shouldn’t say “never” wear shorts because saying “never” is, well, never a good thing. I have worn shorts past age 18. I have some in my wardrobe right now. These tips are primarily for visiting cities where people tend to be a little dressier/stylized. Shorts are hard to pull off in these situations, so my tip is to just leave them behind.

  4. pam says:

    Really great tips Kiki! I always tend to overpack and the night before I’m always sitting in a pile of clothes trying to figure it all out.

  5. Rach says:

    Bravo! I do still wear shorts, but the inseam has increased significantly in the last few years, haha! (they have really cute shorts at GAP) Another great skirt is the jersey skirt from OldNavy, hits a little above the knees, in lots of colors and SUPER comfy, only like $20! If anyone can give tips on being fashionably casual (or casually fashionable?) I’d think it was you! This post is PERFECT as it really shows two of your major strong suits, in both your writing ability and your fasion sense (which I have always been envious of!) Lovely!

  6. Terri says:

    How did you know the girls and I are packing and leaving for a visit to Florida tomorrow? Genius. Love you, TKL

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