Outfit Planning Guide – What Clothes To Pack On Vacation!

So you are going on a vacation! You have everything booked with your travel agent and your itinerary is all planned out. Now you just have to pack before you head off on your fabulous trip. 

There are a lot of different kinds of packers out there. Some people can just throw some clothes in a suitcase the night before they depart and are perfectly happy with what they have with them during their trip. 

When I pack I am the complete opposite of this. I start months in advance with spreadsheets and lists and meticulous outfit plans. The actual packing usually starts a week or more in advance, takes over my entire bedroom at times, and goes on for hours. Believe it or not I enjoy this process.

Now you don’t have to be like me (though if you are, WELCOME!) but if you’d like to be somewhere in the middle of these two styles, feel confident you have packed everything you will need, and take some of the stress out of packing, or just wondering what you should wear on vacation then this blog is for you.

How Do I Outfit Plan?

In this particular blog I am going to cover outfit planning. So first of all what do I mean by outfit planning? This is the process before you pack where you decide what outfit or outfits you and anyone you are packing for will be wearing during your vacation.

I would recommend to start at least two months before your trip, but you could do this as early as you want. 

If you are packing for not only yourself but for your partner, kids, or others you will want to have a plan for each person. If your are traveling with other adults and you want to coordinate your looks but you will not be packing for them then you will want to do your outfit planning in consultation with them. Even if you are the one packing for the whole family it can be a fun activity to discuss and plan some outfits as a family and to get everyones input. This could also mean much smoother sailing when you are actually on vacation because everyone will already be on board with what they will be wearing. 

So what do you use to outfit plan? I have included an outfit planning template here (see end of blog) that you can use as a basic outfit planning list and tool. I suggest using whatever kind of list or graphic that works best for you when you are both planning and then later packing. Once I have decided on an outfit I will lay it out on the bed with all of its parts and photograph it. I will take all of these photos and make a visual list of all the outfits I have planned for the trip. This helps me to visualize the looks all together and finalize my decisions. I will then create a list, usually a spreadsheet, and list every item of every outfit, down to the socks. This is the list I will use when packing, checking off items as I go. 

If you are wondering what outfits do I plan, the answer is all of them. I will pull out my vacation itinerary and take a look at what I will be doing each day. I will take note of how many outfits I will want for each day. I then add a column on my spreadsheet or note my template for each outfit needed.

For example if I am going on a Disney World vacation and my plans for a day look like this:

8:00am – 3:00pm – Animal Kingdom

4:00 – 6:00 – Hotel Break / Pool Time 

7:30 – Dinner Reservation @ California Grill @ The Contemporary

I would plan three outfits for this day, plus pool items, plus pajamas. I would outfit plan for Animal Kingdom, a set of comfy clothes to wear at the hotel, and an outfit for dinner. I would also be sure to list additionally a swimsuit outfit that could be reused throughout the trip or and pajamas. The goal is to prepare for all points in your day. If you prefer to wear one outfit all day of course that is also an option and you would just plan one outfit that would suit you for this day. 

A big part of outfit planning is knowing what the weather is going to be where you are. I recommend checking average temperatures for the month you are visiting for your destination. You can just Google this and it will come up easily. When you get to the physically packing stage you will want to check the forecast for the actual days of your vacation and make sure all your outfit plans are still weather appropriate. Packing a few contingency items incase it is hotter or colder than predicted is always a good idea as well.

Made These Shirts!

Shopping or Crafting

One of the reasons I start my outfit planning so early is because I tend to purchase new items for my outfits. I want to give myself plenty of time to find the pieces I want and to be able to shop sales. 

I tend to shop the most for Disney vacations where my outfits tend to be more meticulously planned and elaborate. 

Some of my favorite options for shopping for Disney clothing and accessories are:

  • Target
  • Khols – Great for matching family shirts
  • Hot Topic 
  • Box Lunch 
  • JC Penny – Best for kid items 
  • Shop Disney aka Disney Store – If you have a Disney Store outlet near you they have some great deals on parks merchandise.
  • Cakeworthy
  • Loungefly – Bags
  • Etsy & Small Shops – There are a ton of small shops and Etsy shops that sell shirts and ears and more. Instagram is also a great place to find these but you can also just google for them. 

If you are someone who likes to make items such as iron on shirts, crafting your own ears, or even sewing an outfit you will want to give yourself plenty of time to complete your projects. Pinterest and Etsy are great places for inspiration.

Disneybounding Example


Disney travelers if you are unfamiliar, Disneybounding is when you wear an outfit that is inspired by a Disney character but it is not quite a costume, the pieces are normal clothes. It’s a great way to bring some extra magic to your day.

I have an whole blog all about Disneybounding check it out here:

How to Disneybound

What Exactly Should I Pack?

Color Matching Wardrobe

A great way to keep the packing light is to plan outfits with a similar color scheme for the week, say you decide to pack outfits with all blue and grey tones. This allows you to reuse pieces in multiple outfits as everything coordinates. Another way to do this is to make sure all of your accessories and outerwear are neutral colors so that they will match any outfit. This way instead of packing 6 cardigans to match each outfit you can just pack one or two neutral ones, or ones that match the color scheme. 

Pack For Your Itinerary

This seems simple but it can be tricky. We all want to look nice in our vacation photos but don’t make yourself or your family miserable all day because they had to wear clothing that not was appropriate for your activities. A day mostly spent hiking is not the time to wear your best jeans. 

Many children want to wear a costume on their Disney World vacation but the standard polyester costumes can be very uncomfortable in the Florida heat after a while. Don’t get me started on the costume shoes no one wants to walk around in those all day. Wear the costume to the park, get the photos, and have a comfy outfit in you day bag waiting for when your little one wants to change. Same goes for adults who want to wear an elaborate outfit at the parks. If you are attending a Disney Halloween party at the parks make sure the costumes you plan follow the party costume guidelines and make sure you consider the weather and the amount of walking you will be doing in the costume when choosing it. As someone who has hobbled back the buses after decided to wear sparkly flats with her Belle costume after a week of non-stop park walking, at least throw the sneakers in your bag they may not be cute but your feet will thank you later. 

If you are visiting somewhere that requires a specific dress code make sure you are aware and following it. The most common of this would be dining locations, if you are planning to have an extra special meal make sure you have planned an outfit that follows the dress code. It is common on cruise ships, resorts, and even a handful of Disney signature restaurants to have a dress code. This is also something to be aware of when traveling and visiting religious locations such as historic churches. Many religious locations have rules about covering your shoulders, or similar. This is an easy fix by planning to bring a shawl or large scarf with you. But make sure you check out the rules for the sites you plan to visit before you go. 

Make sure you are being realistic when you outfit plan. Realistic not only about what you need to be able to do in these outfits but that everyone will be happy and willing to wear what has been planned. This might mean several outfits a day to accommodate everyone and all of your different plans. 

Formal Night On A Disney Cruise (this theme night dress code is not mandatory but several Disney Cruise restaurants do have mandatory dress codes)


When traveling layers are key. Chances are you are going to be in a variety of temperatures throughout your day. Your early morning on late evening activities will be a bit colder than your mid-day explorations. If most of your day is going to be spent outside in the summer but you plan to have a meal indoor you very well may catch a chill from the air conditioning and feel like you need to add another layer even though it is 90 degrees outside. Being able to easily take off or put on a layer will make you a much happier traveler. 

Some key items for this can be accessories, see below for the accessories I suggest based on weather. Make sure you have the correct range with you, not only packed but in your day bag as needed. 

Hiking Outfit complete with a wide brimmed hat. Keep in mind at higher elevations the sun is more intense and it is colder. These pants can convert to shorts and I have a t-shirt under this sweatshirt, plus a package puffy vest, and gloves are in my bag.

Main Items: Shirts, Pants, Dresses & More 

My number one tip is to not pack clothes completely different from what you wear at home. If you only wear jeans and t-shirts in your regular life I wouldn’t pack nothing but dresses on vacation. If your kids never wear flip flops at home don’t only pack them flip flops for vacation.  I like to plan a mixture, shorts, pants, dresses, skirts so I don’t feel like I am wearing the same things all week and I have different looks throughout the trip. Don’t forget those layers when planning. 

For a Disney Parks vacations if you plan to take hotel breaks in the middle of the day don’t underestimate the heat and that you may want to change your outfit halfway though the day. Which means additional outfits to plan and pack. 

This is a category that is really hard to get specific but in this one scenario I will. 

Ladies going to Disney Parks here is my go to favorite park outfit:

  • Sturdy Sneakers
  • Athletic Socks (preferable moister wicking) 
  • Comfy undergarments
  • Slip Shorts or Bike Shorts
  • Lightweight flowy dress or T-shirt and A-line Skirt
  • Cardigan or Jacket 
  • Ears 
  • Hat with a brim: I flip back and forth between ears and a hat depending on the sun exposure. 
  • Sunglasses 
  • Backpack 
    • Hip Pack instead if someone else in the party is carrying a communal backpack. 
  • Accessories that complete my outfit like trading pins, buttons, jewelry, watch 

This is pretty adaptable to any kind of travel just skip the ears. 

I like to plan outfits to match what I am doing that day. I wore a Hamilton shirt I already had to visit Mt. Rushmore. Being able to both theme and use items I already have is the best case scenario.

Under Garments 

 Be comfortable, pack lots of extras. 

Shoes & Socks 

This is where you really don’t want to mess around. 

Pack STUDY shoes, I don’t care where you are going pack at least one pair of broken in study sneakers. 

If you are going to be doing lots of walking on your trip bring two pair so you have a backup if one gets wet, you can also rotate between the two which will help your feet. Looking at you Disney travelers. 

If you are planning a National Parks or similar trip with lots of hiking make sure you invest in legit hiking boots for each member of the family. Don’t forget the hiking socks too. 

I also suggest you pack at least one pair or sandals or less structured shoes to wear if you are just going a very short distance to let your feet breath a little. 

If you are going somewhere rain is a concern you are going to want some rainproof shoes as well based on the kind of trip you are taking.  Be it rain boots, water proof hiking boots, crocs, flip flips, or other water proof shoe. 

Good athletic moister wicking socks will get you a long way.

Matching group shirts can be a lot of fun!

Sleepwear & Hotel Wear

Don’t forget to pack pajamas! I also like to pack some sweats or something really cozy to wear when taking a break at the hotel during the day.


If you are going to be in the water on vacation you don’t want to forget your swimwear. If it is a water heavy trip you will want multiple suits for each person. You’ll want cover-ups as well and don’t forget flip flops or water shoes. If you are going to a water park I highly recommend water shoes! That pavement gets hot!

If you have a little one don’t forget those swim diapers and make sure to check out what kind of life vests etc. may be available at your hotel if you plan to use one for your kids. 

I also suggest packing a wet bag for anything that doesn’t dry before you have to pack back up. 

Alaska Cruisers Prepare For Cold and Rain

Cold Weather

A packable puffy jacket can be your travel best friend. Gloves and a warm hat can be a life saver. Scarfs are great if you are not sure if you will be cold or not as they are easy to layer. If you are going somewhere truly cold invest in a good warm jacket. Ones from companies like North Face that have multiple removable layers are great. Make sure to size the jacket so you can wear layers underneath. Pack hand warmers and thick socks. As well as cold weather gear like Under Amour tights or shirts to wear under your clothes these will keep you much warmer. If it’s a ski vacation or you’re going to be in the real cold make sure to pack all your snow gear.

Hot Weather

Hats with a brim will help keep you cool and protect you from the sun.  Don’t forget the sunglasses. Moister wicking socks are a must. Lighter material clothing when possible. 

A portable fan or ever a wearable one and cooling towels can be life savers as well. 

Even if you are going to a warm destination I suggest packing a warm sweatshirt or light jacket to have incase of a chilly plane, evening, or highly air-conditioned restaurant, etc.

Rainy Weather

A package rain jacket, or it’s cousin the dollar store poncho, is great for almost any vacation but especially a Disney Vacation. Make sure it has a hood. 

If the location is cold and rainy consider a higher end water proof jacket, with a removable cold weather lining that will keep you warm and dry. Make sure to size so that you can wear layers underneath as well.

If you are headed somewhere with a high chance of rain consider waterproofs shoes or boots. 

For Disney Parks I suggest bringing crocs, flip flops, or other water proof shoes and throwing them in your day bag if you know it is going to rain so you can spare your sneakers when the rain starts. At the very least extra socks so you can change them after they get wet. Then make sure you have packed an extra pair of sneaker so when you get back to your room you can dry out the wet pair and wear the second dry pair. 

A Rainy Day at Disney World


Pack lots and lots of face masks, more than you think you will need. 

I wouldn’t suggest bringing any nice jewelry on vacation the risk of losing it, or worrying about losing it is too high. 

Accessories like a scarf, hat, bold jewelry, or belt can really add to the fashion level of an outfit without take up much space. 


Backpacks, backpacks, and backpacks are key for vacation days. Be it one larger backpack for the whole group or smaller ones for everyone, they are key to being able to cary with you the items you need.  Packable backpacks or sting backpacks are great to throw in a larger backpack or purse if you think you may buy something or need more room later in the day or the reverse. I’ll also bring a packable backpack as my hiking bag on trips where there will be hiking and I don’t want to take a nicer bag on the trails. 

Hip bags are great for when you don’t need to bring a lot with you. 

Neutral colored bags can be great because they will match with all your outfits. Or you can go the opposite route and have a bag for each specific outfits it can be a really fun accessory especially when Disneybouding. 

A variety of styles of bags, cross body, backpack, hip bag can be good as well to spare your back and shoulders from having the same weight distribution on them during the whole trip. 

Work Out

If you like to work out during vacation make sure you pack your work out gear. This is another great use for a wet bag to keep sweaty clothes contained when you have to repack. Runners don’t forget the running shoes. Make sure you have the right headphones are well, one thing to consider is many hotel treadmills have tv’s in them but you will need plug in headphones to use them which the hotel may or may not provide. Plus any accessories you might need like a yoga mat, water belt, or others.


Things sometimes don’t go according to plan, pack emergency extras. 

Dole Whip Outfit at Aulani

I hope this helped you get a better idea of what outfits to plan on your vacation and what sorts of clothing to pack.

If you are looking to travel I would love to be your travel agent. Get expert advice in planning your vacation and a personalized experience at no additional cost to you. 

Contact me at katiev@themagicsyours.com

Follow Me!   https://linktr.ee/katiethemagicsyours

Download the planning sheet below and start planning your own outfits!

Published by katiethemagicsyours

Hi, I’m Katie! I’m an independent travel agent with The Magic’s Yours Travel. I specialize in Disney vacations but I book all sorts of travel all over the world. I book Disney, Universal, cruise, resort, all-inclusive, hotel, and guided travel. All of my travel agent services are FREE of charge to the traveler. You pay no extra fees for using a travel agent, but you get an expert in your corner to offer you VIP planing services. Contact me for a free quote today. Email me at: katiev@themagicsyours.com

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