How to Plan Your Packing for a Perfectly Stylish Vacation

Miss Traveller Vintage Hat box How to Plan Your Packing for a Perfectly Stylish Vacation

My little junior vintage hatbox

Every week I get emails from readers asking the same questions; how do you pack when you travel? And while the destinations may vary, the principles of successful holiday packing do not. What I’m going to share with you is the thought process behind the how and why of my packing system.  It won’t be an expensive list of things to buy and how to create a carefree Riviera look. But it is a plan that you can apply yourself; whatever your style and wherever your destination.

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1. How much space do I need?

Even before I begin to think about what might be needed to wear, I firstly start to build a picture in my mind of just how much luggage I’ll need. Here’s what you need to think about-

What is the airline’s luggage weight limit?

Will I have to carry these bags alone and how many changes of transport will I have to do that for?

Will the luggage be so big and heavy that I’ll need work boots just to drag it around? (Oh so very un-glam)

How much shopping will I be doing? At which destinations and what size of items do I intend to bring back?

Are there different luggage weight allowances on internal domestic flights in the areas I’m visiting?

You may be able to tell from this list that these are tips I’ve learnt over time, sometimes the hard way. And one other hard and fast rule I’ve learnt to apply is this; never bring large carry on. Not only are you not guaranteed a space for this, but it leaves you no wiggle room for that magic luggage expansion that happens on the very last day of your trip.

Keep hand luggage to a minimum both for your own comfort and speed of boarding flights.  Generally my hand luggage consists of those things that are irreplaceable like my vintage hats and jewellery; even then I keep it small so I don’t have to carry too much around airports.

Now that you have a mental picture of the size of luggage you need to bring, you can start thinking about the weather, activities and events you’ll be enjoying at your destination. Here is my secret trick to planning the perfect outfits…. I simply imagine the hollywood film version of myself on holidays. What does movie me wear for dinner on the beach, or when dancing a tango, or simply lazing in the shade with a book? Sure, it’s a romanticised version, but it is a great launch pad for ideas.

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2. Write it down

For each possible activity I write down a generic description of what I need to wear. Swimming? Bathers and something to wear over them. Shopping on a hot day? Long cool dresses and good walking shoes.  Once you have this little list down you can start thinking of which items fit the bill.

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3. Pick a pallette

Choosing a basic wardrobe colour palette for your trip is the key to making a few pieces go a very long way. It also saves you from needing to pack a large selection of bulky matching shoes. On my last trip I picked a base palette of red, white and blue, allowing myself a bit of green in there too as an accent colour. Here is the overview of my outfits for a two week trip-

what to pack for a tropical holiday vacation How to Plan Your Packing for a Perfectly Stylish Vacation

This is what my bed looked like as I packed for my two weeks away. I haven’t pictured accessories, underwear or toiletries here so this isn’t the sum total of my suitcase content. But aside from those other small items, this is it. Keep in mind that I was away for two weeks; one at a beach and the other a lively city.  I needed to dress for heat, humidity, walking, lazing, shopping, dinners, conferences and meetings.

In the interest of illustration and helping you piece all this together, I’m going to break it down.

Firstly; scarves, pashminas and sweaters.

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packing for a holiday vacation scarves and pashminas How to Plan Your Packing for a Perfectly Stylish Vacation

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You’ll notice that the colours I’ve selected all work within my defined palette for the trip. I had two pashminas, two little cropped sweaters and one long polka dotted scarf.  These will be your best friends on a summer holiday.  When you are in and out of air conditioning, dining as the evening cools, or simply looking to cover bare skin for modesty; these all do the trick.

The secret is to find pieces that are made in good quality yarns and with a very fine weave. That way they roll up to nothing and you can always carry one in your handbag. The ones I packed are made of angora, cashmere and silk. Breathable, natural and investments that will last you ages if you take care of them.

Let’s break down the rest of the key pieces…

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what to pack for a tropical holiday vacation wardrobe How to Plan Your Packing for a Perfectly Stylish Vacation

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Far left from top down

Zebra print sheer beach cover up – can be worn over swimwear or over singlet tops. Just belt for shape and add some great jewellery.

Black lightweight cotton skirt – made of cotton voile this works for beach wear, dinner wear and day wear. Separates are your friends.

Bikini - I will only wear this at the pool. Not to the shops, not to dinner, and certainly not to play table tennis in as I saw some girls doing.

Leopard print dress – Again a light weight cotton dress with a shirred waist line, primarily worn poolside. On it’s own it is a bit basic (even in spite of the print), but with a black cinch belt, great shoes and a chunky bangle it becomes far more chic daywear. I wouldn’t wear this one to a more formal evening out as the cotton is too light weight to be fancy enough for my taste.

Center from top down.

Stripped peasant style top – again light weight cotton, but super fitted with a side zip. Cute with long or shorts skirts, heels or flats.

Red faux silk dress – cool, comfortable and will take you from the shops to a night out at dinner. Just change up the height of your heels, add a little cropped cardigan and a flower in your hair.

Gingham halter neck dress – Day or night, gingham works, It doesn’t translate to more formal settings, but a beachside dinner, or wine and tapas at a local cafe; gingham and halters come together to make you feel all Roman Holiday.

Red winged bust top – One of my best friends. Because it is so structured with boning, shirring and a convertible and removable halter strap; these babies will take you anywhere. With a cropped sweater , to make the best feature of your waist line, these can become chic little tops for cocktails when paired with an ankle length skirt.

1940′s reproduction 2 piece swim suit - yes, for swimming; but the top piece can also work as as singlet top for cute casual day wear. To make it look less like swimwear, I like to pin a large fabric flower onto one of the should straps at the neckline.

Far right, from the top down.

Large brimmed red hat (out of shot) – for sun protection, drama and mystery. See also hangover cures.

Navy and White ankle length jersey skirt - bloody brilliant! Whether in stripes or a solid colour, a long jersey skirt will take you easily from a comfortable plane ride to a swanky dinner. It can be worn with almost any style of top (steering away from the cut off versions to avoid any muffin incidents), and looks equally as great with flats as it does with heels.

Blue cotton voile 1950′s reproduction day dress – This one will do secret rendezvous, lunch dates, and with a few rhinestones for good measure; even a formal evening dinner.

Blue winged bust top – read the description of the red winged bust top so I don’t keep gushing about these.

Hawaiian print dress – Happy hour anywhere!

Khaki culottes - They are the skirt that isn’t a skirt, the solution to more active pursuits that can’t be handled in a skirt, and far cooler and more forgiving than jeans. The French know their stuff.

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4. How to Accessorize

Picking a small but cohesive selection of accessories is key to getting several different looks from each of your outfits. These make the difference of day to night, formal to casual and are also the way you introduce your own personalised flair to each outfit. Here’s what I took to change up my outfits.

Belts – Simple, inexpensive elastic cinch belts in black, red and blue

Jewellery – For day time I chose chunky beads and a scrimshaw bangle in red or white. For evening I picked clear diamontes. A small necklace, super sparkly earrings and a pair of dress clips that you can wear on tops, shoes, bags or even in your hair.

Flowers – Both fabric corsages and faux flower pieces.  Each one has both a crocodile clip and a brooch clip on the back; that way they can be pinned on hair, bags, shirt, hats, used to keep scarves together.. you name it! A selection of four key colours and you’re good to go.

Shoes – two pairs of wedge heels, one black ballet flats and one pair of flip flops for the pool. That was it! Not having any short skirts in my capsule wardrobe meant that flats and wedges would work for any occasion. I stuck with red, black and one bright floral pair for a bit of fun.

what to pack for travel shoes How to Plan Your Packing for a Perfectly Stylish Vacation

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All in all, there really isn’t all that much here; but each piece (minus the bikini) must do at least three different outfit combinations, otherwise it just doesn’t make the cut.

5. The Finishing Touches

Just as they do every day at home, the finishing touches to your holiday outfit are what take your look from clueless tourist to chic international traveller. And what are they? Your hair and makeup. Being well groomed at all times on your holidays not only makes you feel better but it will save you money too. Hear me out on this one…

When you find yourself in a new city or even at a fancy resort, you are constantly bombarded with images of good looking people, just as you are at home. It may be the pictures of the gorgeous lady getting a massage at the spa, or it may be the urban dwellers you’re bumping shoulders with over a sale rack.  Nothing will make you reach for your wallet on holidays faster than when you feel inadequate. Yes, it happens to everyone no matter how much above it we’d like to think we are.

When you’ve given your outfits careful consideration as to when and where you’ll be wearing them, you need to pay equal attention to your hair and makeup.  Learn some quick and easy styles that don’t take an hour with the straightener each morning. If you’re going somewhere humid and your hair hates you, be prepared. Pack a small bottle of macadamia oil for emergency smoothing and plan some sleek styles that avoid the issue altogether.

Makeup needs to be simple, straightforward and climate friendly; but even when at the beach I don’t leave my red lipstick at home. I just pick the right formulas. Heavily tinted lip stains, mineral makeup that doesn’t melt and waterproof everything else. ( Come to think of it I really need to write a whole post on ‘beach face’).

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In short, consider the whole package. Does it live up to that ‘movie’ version of the holiday in your head, and will that woman wear what you’ve chosen for her? Is it too much hard work or do you need to simplify?

Once you’ve got the basic strategy down, you can mould it until it is the perfect fit for you. It works for summer or winter, the simple holidays or the fancy.  I’ve written a hell of a lot here, and as I’ve deconstructed what comes naturally to me, I realise that it isn’t about the little details of what I took, but why I packed each piece. And I’m hoping you can see the big picture emerge from all of this.

Of course, this may leave you with even more questions and you’re always welcome to ask away in the comments section. But for now, go forth and know you can really relax when you get to your destination; packing ninja that you are!

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Candice DeVille

Specialty Vintage Stylist, Blogger, and Presenter; Candice DeVille has been writing Super Kawaii Mama since early 2008. Based in Melbourne, Australia, she's always in search of the next glamorous adventure. Bringing you vintage style, glamour and inspiration for the 21st Century.
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17 Comments

  1. Wonderful list :) Some good tips for backpackers to your land as well actually! Where are those ‘winged bust tops’ from though? They look amazing!
    Cee recently posted..Confession to Dress-slaughter

  2. This is such a timely post SKM – I’ll be going to Fiji in June (my first “island holiday”) for a friends wedding. It was only last night that I wrote down a list of what I should take.

    Thanks so much for the tip on taking pashminas etc as I hadn’t put that on my list, assuming Fiji would be warm all hours…but thinking about it now, it could get chilly and a wrap of some sort would provide just the right amount of protection.

    I’m now on the hunt for a pair of fuschia/pink wedges that will somehow pair nicely with this dress http://www.etsy.com/listing/61978285/reserved-for-kittymeow84-a-sculptured – which will be what I’ll wear to the wedding. Possibly a bit OTT for an island but hey what’s that phrase about preferring to be overdressed? ;-)
    And then there’s the trouble of finding shoes that will be kayaking/reef appropriate without looking fugly and also pleasing my boyfriends desires to go ‘adventuring’. THAT will be the real challenge.

    Anyways, I’ve written an essay! Great post SKM :-D
    Esz recently posted..Butterick 6876 – Button Front Dress Pic HEAVY

  3. Great post SKM – love your words about saving money too. You’re so right! I’m more inlclined to add to my wardrobe when travelling that at any other time and now I know why – I need to glam up a bit more!
    Nicole Jenkins recently posted..Shame- Livia

  4. Excellent post! Hmmmm, must go book another holiday…
    Jenni recently posted..FABRIC THERAPY

  5. We have the same bikini! Love it xoxo
    Veronica Darling recently posted..Sneak Peak- Colette for Sew Weekly

  6. Wow! I don’t think I’ll ever pack the same again. I’ve never thought about using a color palette. That would sure cut down on the shoes! I always feel like I need an extra bag for shoes.
    Stephanie recently posted..Life is like a box of chocolates-yummy!

  7. Thanks for posting this SKM. I think you did one a little while back that was very similar and certainly made my packing to my trip to HK last year oh so easy. I travelled there with a practically empty suitcase because I didn’t pack fifteen pairs of shoes! (we won’t talk about the part coming home…)

    Having a colour palette is the best thing you ever suggested. I now travel normally in black and white with an accent colour (normally blue or red). It works a charm!
    Wild Tea Party recently posted..Waving goodbye to summer

  8. Love this post SKM. I am going away soon (on my own!!!) for a couple of days and am going to put much more thought into how I pack.
    PlanningQueen recently posted..Ethical and Healthy Fundraising – Your Chance To Win!

  9. I’m not traveling anytime soon, but you’ve given me a fresh attitude with this post. (And with the inspiration of your beautiful photos!) I’m getting ready for work, and I’m thinking, “What would Hollywood Film Star Me be wearing to work today as a legal secretary on casual day?”
    Holly recently posted..Honkus Grogana featured in a blog!

  10. Mrs Aunty Leroy /

    Dear Mrs SKM,

    I finally came to the realisation that with 2 children and a husband my back packing days were over and the tatty faithful backpack was consigned to the bin.

    Your praiseworthy advice will make my resort style holiday to Fiji a lot more glam and a lot less cumbersome. Color scheme packing simple but deadly glamorous. Thank you ever so much.

    I humbly seek your advice and that of Ms Lebeaux for a solution to lipsticks that have suffered at the hands of my 2yo. Little Miss Weewoy has broken the top off 3 of my favourite lipsticks. One had the name “vintage pink” so you can surely imagine my lamentations. Trying to apply these lipsticks with only a brush is laborious and makes me start the day waiing ‘oh why oh why did I leave my handbag out’

    Any suggestions you might have will be greatly appreciated. Once again thank you kindly for your packing tips.

    Mrs Aunty Leroy

  11. One of the best travel outfit planning posts I’ve read, great details. I particularly concur with feeling inadequate and the shopping correlation. I am planning for a 4 week trip and I feel a bit more prepared now, thank you.

  12. Felicity /

    Where did you buy your vintage hatbox, it is really amazinggg :)

    • Super Kawaii Mama /

      Felicity: I found this one via Etsy. It’s an original early 1960′s junior hat box. :)

  13. Felicity /

    Thank you so much, it is really wonderfull :)

  14. Great post! It’s really helpful and fun to read! You broke down packing into a few easy to follow steps and the great picture of your post definitely became clear! It’s nice to hear that you, too, imagine a Hollywood version of yourself on holiday! :) Not all of your tips are totally new to me, but your post makes me think more thoroughly about what items I need to pack and why, so that I won’t end up with some pieces that I eventually won’t wear and that will only take up space in my suitcase that could be filled with some new things bought abroad instead. So, I’m happily off to plan my packing now :) Thank you!

    • Super Kawaii Mama /

      Sesame: Thank you, so glad it was helpful. I’m always improving those skills and last trip fitted everything into one carry bag! I surprised even myself. :)

      • Your post did not only inspire the contents of my suitcase but also the contents of my latest blog post which you can find here, if you want:

        http://bit.ly/10uOHAX

        I needed more space than a carry bag provides, though, but fortunately there will be more occasions where my packing skills can be practiced :) Thanks again!

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  1. Stylish Thoughts – Super Kawaii Mama - [...] What are your top tips for looking stylish when travelling? Pick a colour palette, plan for occasions and never underdress. …
  2. Getting Organised For Going Away……ON MY OWN! | Planning With Kids - [...] winter, I have a new pair of ballet flats and some skinny black jeans. I also took the advice …

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