Strategic Dressing Vacation Style Wardrobe Planning

Only Carry-On? Part 3: Outfit Planning With Your Smartphone

A blue shirt and some shoes on top of the bed

Outfit planning is a fast-track way to turn your post-vacation mantra from “I barely wore half of what I lugged around the Mediterranean” to “packing is my super-power”. I touched briefly on the value of outfit planning in the previous Carry-On Only posts Part 1 and Part 2. Now I want to delve in to the nitty-gritty of planning a week of outfits for travel (of note: this is also a fantastic way to build a capsule wardrobe!).

It is so very true that outfit planning is a sure-fire way to increase your stylishness. Ultimately, you can still spontaneously toss everything you think you will need into your travel bag and go. But this here is a guide to help you be your most stylish self on your trip, using a limited, carry-on-appropriate amount of items. And that, my lovelies, requires a little bit of outfit planning.

The Capsule Wardrobe Creation Part of Outfit Planning

There are two ways to consider how to pre-plan what you will wear on vacation. You can plan what you will wear each moment of your trip based on each planned or spontaneous activity you might have. On the other hand, you could plan numerous outfits and select a suitable one on each morning of your trip. Both options can allow you to bring the minimal items of clothing so as to allow it all to fit in your carry-on.

A white hat with black ribbon on top of it.

Panama Hat, Purchased 2013

Step One

I’ll outline the most thorough way to do your outfit planning. Start by listing all the days you will be away from home, including your travelling days. On each date, list the planned and potential spontaneous activities, and the likely weather and temperature you will encounter for the day. This will help you know if you need to include a sun hat, a warm layer like a sweater, or closed-toe shoes with socks for each specific day. Write down if there will be extra walking requirements, making comfortable shoes a priority. Perhaps slip-on shoes with socks or sock-ettes are a necessity, such as when moving through airport security. Note if the day requires a dressier outfit, like for attending pre-wedding activities. Specify if you can rely on something more casual, like for a beach walk along with some small-town touring.

Step Two

Once you are have noted the formality requirements and necessary extra pieces for each day, look at the listed activities. Decide if pants or jeans will work, if you would like to wear a dress or a skirt on a specific day, and make a note of each.

A pink dress is shown with a white background.

Coral Dress, Purchased 2012

Step Three

Now look at the list as a whole. What items overlap several days? Maybe you need to wear non-denim pants for more than half of your trip. Your neutral-coloured ankle pants may work with your non-athletic runners for a walking tour of a city’s inner secrets. Those same pants will go with your pointy-toe flats for lunch at a bistro. For your dressier events, likely the same dress will work several times. Perhaps one part-way fancy dress will be as suitable for a wedding rehearsal dinner as for the next week’s art gallery visit. To maximize the versatility of that dress you plan to multi-wear, choose a dress that can be worn several different ways. Plan enough pieces that you are not wearing the same piece two days in a row. At the same time, make sure each piece you choose to bring works hard in your travel wardrobe.

A dress that is on the floor.

Chambray Dress, Purchased 2005

Step Four

So you’ve determined that you can get away with, say, two pairs of pants, one pair of jeans and two dresses. The next trick to make this kind of outfit planning work is to have all the pieces work together. Pick a neutral colour as your base, such as white, blue, or, the common fall-back colour, black. Choose two or three accent colours and stick with those as you plan looks from the clothes in your closet. For the outfits planned out here, my neutral base colour is white accented with coral and chambray blue. Colour cohesiveness means that the clothing items you bring can easily do double duty. In this planning stage, you can easily mix-and-match the pieces you pack to maximize the number of outfits you can create.

Vital for this stylish traveller carry-on only outfit planning thing to work? Do not bring more than three pairs of shoes. You will survive. And you will be more savvy and coordinated along the way.

The Smartphone Part of Outfit Planning

A woman in a white jacket and pink dress.

Your smartphone will come in very handy for creating your own dressing guide. Lately, it seems to be surgically attached to our hands, anyway. For years I have made Outfit Ideas lists in a sleek little leather-bound notebook that sits on my nightstand. When I travelled, I wrote out the list of each day’s outfit on a separate sheet and carried it in my suitcase for referencing during my journey. Now I rely on photos I take with my smartphone of items laid out on my bed or of me in the outfit. I’m still pretty terrible at taking selfies, but it doesn’t really matter. These pictures are only for me.

A red shirt, white pants and sandals on top of a bed.

Why a Smartphone?

The ability to reference a picture of an outfit with all of the pieces you plan to wear will help you get your butt out of your hotel room fast. It will get you on with your day, full of doing everything or nothing. Leave your clothes rolled up in your packing cubes. If you feel like it, put all the still-packed packing cubes from your carry-on luggage right into the dresser drawers. Easy, and stylish.

A woman in blue dress taking selfie with phone.

Back to your outfit planning list. Once you have written out the outfit you planned for each day, lay the entire outfit on your bed with all the accessories that it requires. Photograph that flatlay with your smartphone. If you prefer, put on your outfit and take a picture of it while you are standing in front of a mirror. This must be what selfies were invented for. As a rule, don’t worry about how your hair looks or if your polish is chipped in these photos. That part doesn’t matter in outfit planning selfies. Group copies of all these vacation outfit photos in a folder in your smartphone’s photo album. Label the folder or album with the name of the trip. Oh, and don’t feel like you need to include these shots in your vacation slide show. Not a stylish move.

A woman in jeans and a white jacket holding her phone.

When you are on your vacation, before you even roll out of bed, you can scroll through your outfit photos. Ahead-of-time outfit planning with your smartphone ensures that you have don’t have to waste vacation time to figure out what to wear. Outfit planning is a rockstar move that keeps you stylish and ready for anything your vacation might throw at you. Even if you haven’t pulled out your inner rock star since you rocked ombre hair.

The Joy of Style

At The Joy of Style, we thrive on outfit planning. It’s what makes for a wearable, hard-working and stylish wardrobe. We can help you achieve a highly functional wardrobe for your vacation plans, or for your everyday life. Contact us before your next suitcase full of nothing to wear.

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