Does Vacation Packing = Anxiety for You? 

Oh man, vacation packing is a top of mind topic right now! With winter break upon us, many of my personal styling clients as well as blog readers are borderline stressed because they’re getting ready to travel for the first time in YEARS! When it comes to packing for a vacation we are all out of practice.

And packing, even in non-covid time, is an anxiety producing task. What to take? How not to overpack? Making sure you have all that you need. Does it all go together? Does it still fit? Will it fit in one bag? And not surpass the weight restriction? And these worries are just the first few that came to mind - there are so many more… So, I’m going to take you along on my packing journey to give you a glimpse into the packing process of a personal stylist.

My Dirty Little Secret… I Hate Packing for Myself too!

When it comes to packing for myself, I HATE it, with a passion. I’m not intrinsically a good packer. I think (or at least justify) that it’s because dressing for me is a very emotional and creative process. And limiting myself to only the items I pack feels stifling. There are so many variables that factor into my OOTD (outfit of the day) choices. In my dream scenario, I’d be able to transport my entire closet with me to my vacation destination, so I could pick out exactly what I felt like wearing on that day and have all of my options available. But sucks for me, that dream ain’t ever going to be a reality.

But Packing for Clients is Easy Peasy

When I pack for clients however, it’s easy peasy. I joke that it’s like giving a friend advice about a boyfriend (yes, it’s been decades since I was dating but I remember the feeling well). It can feel slightly hypocritical because I can dish out the precise advice about what needs to be done and can see it so clearly for someone else. But taking that same advice and applying it to myself is exponentially more difficult. Ya feel me on this?

So I’ve developed one process that works for my clients - when I have the objectivity to see clearly what’s needed and what’s not. And then I’ve adapted that process into one that is a bit more tedious, but applies the same principles that I use for myself - because I need to play out my gazillion what if’s and process it as I pack for a trip. 

So I’m going to share the process as it applies for a client - and then the adaptations I make to accommodate my own packing mishegoss.

Washer + Dryer?

First and foremost, will you have access to laundry during your trip? If so, you can likely cut down on the number of items you’re planning to bring. Especially things like undergarments, socks and exercise clothes that take up a lot of space.

Vacation Packing: My 10 Step Process

1.Start with the Itinerary and the Weather Forecast

Even if you don’t have an exact itinerary (meaning you’re not going on an organized tour) think about how many days you’ll be away. And what your days and nights will entail. A Lot of walking? Sport activities? Fancy dinners? Casual grab and go meals? Seeing friends or family? Try to lay out approximately what you’ll be doing each day and evening.

Then look at the weather. I like to print out the 10 day forecast for my destination (or destinations, plural). This allows me to forecast (haha, see what I did there?) the temperature range and match that back to the itinerary.

I’m showing a sample of a client’s VIRTUAL CLOSET below, and the weather outlook I include. The temps range from mid 50’s to high 80’s - so when I packed her I focused on items that could be layered. BTW, this is a great tip even if the temps at your destination are not as drastically different because days can be warmer and evenings cooler. And indoor air conditioning (or heat) is often so different from the outside temp that layers are needed just going from outdoors to indoors.  

2. Do NOT Try Out New Items for a Vacation

A vacation is NOT the time to try out new clothes, and especially not new shoes. New shoes + a walking vacation = blister city. When packing for a vacation the outfits need to be good and versatile, not earth shattering. Opt for your tried and true ensembles rather than your wow outfits. The other good thing about this tip is it prevents that panic, impulse shopping that many people do before an event or trip. Typically those purchases are costly and are the mis-buys I find in people's closets when we do a wardrobe analysis.

3. Look at your OOTD’s

You don’t have to be a fashion blogger to take OOTD’s. In fact, it’s something I encourage my styling clients to do regularly. I could go on and on about the benefits of mirror selfie photos - but when it comes to packing the magic of the ootd selfie is this… You can go into your photos and see what you wore (and loved) in whatever month has similar weather to where you’re going on vacation. Then pull out the pieces in those outfits and use that as your starting point for your pack.

4. Pull According to Category 

I do this for both clients and myself. I pull all of the pieces I think would work for the vacation (often using the OOTD’s to jog my memory), and organize them according to category. All of the pants together, all of the tops together etc. This is helpful for two reasons. First, it allows us to see if we have way too many or too few in a particular category. And it also lets us see at a glance if there is a lot of redundancy.

When packing you want to limit as much redundancy as possible. If one shoe can work with multiple outfits, you don’t need to pack the similar pair. BUT, if it doesn’t (trust me, my husband has questioned me many times why I need 2 or 3 pairs of black shoes for one trip - and sometimes I JUST do!) then you need to make sure the item can be used in a few outfits. If it’s a one off piece (meaning it only works with one outfit) then think about leaving it (and maybe the whole outfit) at home. The one exception to this is if you’re going to an event like a wedding - then the wedding outfit will be a one off and that’s OK.

Here is what I virtually pulled for my client to bring to a multi-city vacation in California - I did the same virtually - pulled a lot and then narrowed it down according to what I used most when creating outfits.

5. Now Try it All On - I’m not joking

As much as it’s a pain in the a**It's a necessary step to make sure everything fits well and works together. This step also prevents the disappointment that can happen when you lay out an outfit and it looks good off, but then you put it on and it’s no bueno. Especially as women, our weight can fluctuate. And the pants that fit great 3 months ago might be too big or too small now. So my best, most important advice is to TRY IT ON before you pack it!

By doing a mini try on BEFORE you pack, you can vet out the individual items and the complete outfits you’re thinking about bringing on the vacation. So only the most flattering and useful items make it into the suitcase.

6. See What Items Can be Used in Multiple Ways

While trying everything on, create outfits. Start with bottoms and build 2-3 outfits that fit into an aspect of your itinerary. i.e., how to wear the pants for daytime shopping and again for a dinner out. 

See what pieces are used often and which are used only once - those used only once can stay home.

And as you’re creating these outfits TAKE PHOTOS of them. That way you will have a visual representation of what outfits you packed for what occasion.

When I do this for my clients I create collages for each outfit that they then keep in their virtual closet (housed on their phone, IPad or computer). But when I do this for myself, I just take mirror selfies. Here’s an example of some of the outfits I made for my client going to California.

7. Make Sure Every Outfit has Layers

Remember earlier I was talking about layers? They’re essential for travel because they create interest in an outfit. And they allow for temperature changes too. Every outfit, day or night should have the ability to peel a layer off or add one on.

8. Don’t Forget the Accessories

Accessories are the easiest to pack (necklaces, belts, scarves) and offer the most outfit pizzaz for the room they take up in your suitcase. Accessories are your travel BFF’s.

9. Count the Outfits

Once you have the outfits pictured you can count and see if what was created matched up to the number of days you’ll be away and the amount of activities you had on the itinerary.

Typically what’s been created is more than what’s needed - so then you can pare down - aka take less. I typically suggest having at least 1-2 extra outfits just in case. But these extras should be made up of items you’re taking on the trip anyway.

10. Take Out the Extras + Pack it Up

I think you’ll be surprised at how easy this makes packing. It’s one of those “prior planning prevents piss poor performance” sort of exercises - and it really works. Once all of the items and outfits have been reviewed, the pieces that were only in one outfit can go back into your closet. And you’re all ready to gooooo!

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