đ§ł Style Mail: How you can pack better...next time
A bonus post - because I couldn't wait to share this!
A couple of weeks ago, I wrote an article about packing (click here if you missed it). And it not only includes one of the most important things to remember when you pack - it also includes links to the packing strategies that Iâve shared over the years.
But then I was thinking - how can you figure out the best way to pack for you? How can you look at what worked on recent trips & replicate it? And how can you use your past mistakes to your advantage? So, I came up with the idea of âvacation packing hindsightâ.
My background (before becoming a stylist) was corporate retail. And hindsighting a business season was a big part of planning the next one. So, I thought it could be a helpful way to pack better - because I donât think many people return from vacation & objectively look at what was in their luggage (I just consider it a win if I unpack in less than a week!).
So, here are specific things that you can do before, during & after your trips - so you can see what worked, learn from what didnât work, recognize your tendencies & become an expert at packing for yourself.
âď¸ Style Scoop

Since this is an off-cycle post (youâll still hear from me later this week with a bunch of mid-summer style strategies), Iâm going to be as concise as possible. So, here are the steps to âvacation packing hindsightâ.
BEFORE THE TRIP:
Write a list of what you pack (Iâll get back to list-making later). Write down everything youâre bringing & be specific - clothes, accessories, toiletries, etc. And this includes what you put in your carryon & what you pack in your bag(s).
DURING THE TRIP:
Take selfies. Every day & every outfit change. And you can even write down how you feel about your outfits - everything from how it worked for your activities to how you feel wearing it (physically, mentally, emotionally - hereâs more on that subject).
Iâve talked a lot about the process of taking selfies & writing down how you feel in Style Mail VIP - so if youâre not already a VIP, now is a great time to sign up.
AFTER THE TRIP:
Look at your pre-trip list to figure out what you brought vs. what you actually wore. This may be as easy as looking at whatâs in the laundry bag vs. what isnât - or going through your selfies as you unpack. Then itâs easy to compile a few other lists.
Write a âwhat I woreâ list & include any additional ideas you have about how these outfits felt, functioned, etc.
Write a âwhat I didnât wearâ list & jot down some notes about why (was it pure circumstance - like the weather was unexpected? or was it one too many dresses?).
And if itâs appropriate, write a âwhat I wish I packedâ list - if you feel like you could have made different choices. These lists can be as brief or as detailed as you like. And itâs not about berating yourself for any bad decisions - itâs about being objective & realistic about what did (and didnât) work & why.
And now itâs hindsight time. Take a look at your habits - what you bring & donât wear, what you wear multiple times, what you often forget, how you feel about your vacation outfits, etc. And if youâre up for it, write some things down. You may realize youâre better at packing than you thought. You may realize that youâre packing for what you hope may happen on the trip (but it doesnât relate to your actual agenda). You may realize that, in hopes of packing perfectly, you could use a few more things. Or you may realize that you need to revisit how much time you give yourself to pack.
BEFORE YOUR NEXT TRIP:
Review your hindsight info. Because you may not remember everything.
And then write some standard travel lists - like:
The âalwaysâ items - toiletries, pjs, underwear, lounge clothes (watch this Instagram post if lounge clothes arenât already a must-pack), phone chargers, etc. etc. etc.
Items for often visited locations (or similar types of trips). This might be a âhot weather vacationâ list or a âvisiting family for the holidaysâ list or a âweekend at the lakeâ list. (I have a standard trip list & then a separate list for when I visit my parents, since there are a bunch of things I already have at their house.)
Items that you learn are must-haves for you on every trip. Like a compact umbrella & folds-into-a-bag rain jacket. Or cozy slippers. Or an extra white t-shirt.
The goal with these lists is to never forget anything - and to consciously decide what you are/arenât bringing. And the goal with hindsighting is to recognize any habits that may get in the way of packing well - and subsequently effect how you enjoy your trip.
Do you have any other things that help you pack well (that you do before, during or after vacation)? Leave a comment so we can all learn from each other.
âď¸ One more thing
Not to be all âlist-happyâ - but I write a list of what Iâm packing for every single trip. This happens way before the trip in the notes app on my phone - so I can write down things as I think of them. And it helps me to be planful with my outfits & how they relate to my agenda, the number of days Iâm away, etc.
And then, if your luggage is ever lost, you know exactly what was in it!
My packing depends on how early I start - when I start way ahead of time, I plan outfits, make sure things mix and match, try each outfit on and make sure it works, etc. When it's a last minute rush, I always throw in "just in case" items that I usually don't use. One thing I no longer pack is workout clothes. I realized that when I'm already walking 20K steps a day sightseeing, there is NO WAY I'm going to get up early and go to the hotel gym to do a separate workout! I do pack a set of lounge clothes and always have a pair of slide sandals in my bag. I use the stylebook app to create a packing list and save outfit ideas for the pieces I pack, which is super helpful when I'm halfway around the world and my brain can't remember what I was going to wear :)
Great tips here! I just went on safari and really struggled with what to bring. Partly, because you are limited to one soft bag that weighs no more than 44lbs (small planes). I did lay out everything on my bed and took a picture before packing the bag. I also noted in my journal the few items I didnât wear and what I wished I had packed. I may never go on safari again, but it was a good exercise. This post was a good reminder to do that for other trips.