There is a very specific kind of pressure that has grown up around travel and vacation styling in the last decade or so, and I think it’s worth naming before we talk about anything else.
It is the pressure of the travel aesthetic. The curated resort looks. The carefully planned outfits for each location, designed to photograph beautifully against the right backdrops. The sun-drenched images that look effortless and take, you suspect, considerably more effort than they let on.
I’m not opposed to beautiful travel photographs or considered outfits. But I’ve noticed that for a lot of people — especially those who are already carrying stress, who are going on vacation partly to recover, who have limited time and energy and want to actually rest — this pressure turns packing into a project that creates almost as much anxiety as the trip is supposed to relieve.
What would it look like to dress for vacation with a completely different set of intentions?
What Vacation Styling Is Actually For
Before thinking about what to pack, I want to offer a question worth sitting with: what do you actually want from this trip?
Not what you want to post, not what you want to look like in photos, not what version of yourself you want to project to the world or to your future self scrolling through memories. But what do you actually want to feel on this vacation?
Do you want to feel light and easy, completely unencumbered? Do you want to feel a little elevated and put-together because that genuinely makes you feel more like yourself? Do you want to feel adventurous, or romantic, or completely anonymous in the best possible way?
These are legitimate, different answers, and they lead to genuinely different packing decisions. The only wrong answer is the one that prioritizes appearance over experience.
The Cost of Overpacking and Underpacking
Most of the vacation packing misery I’ve heard described falls into two categories.
Overpacking: You bring everything you might possibly want to wear, create a dozen potential outfits, and then spend a meaningful portion of your mental energy while traveling managing, choosing, and second-guessing them. You check a bag unnecessarily. You spend more time getting dressed than you wanted to. The abundance of options becomes its own kind of noise.
Underpacking with the wrong things: You brought practical items but forgot what actually makes you feel good. You’re at a beautiful dinner and you have nothing that feels right for the moment. You spend the trip slightly uncomfortable, slightly off, in a way that has nothing to do with the destination.
Both of these are solved by the same thing: knowing, in advance, what you actually want from this trip, and packing precisely in service of that.
A Different Approach to Building a Travel Wardrobe
Here are the principles I use in working with clients on travel styling:
Pack for activities, not occasions. What are you actually doing on this trip? If you’re hiking half the time and going to dinner the other half, pack for those two things. Not for the fantasy of additional activities you might do but probably won’t.
Build around a color story. Two or three colors that work together means everything you bring can be worn with everything else. This is not an aesthetic restriction — it’s a practical freedom. When any top works with any bottom, you have more actual options with fewer pieces.
Distinguish between comfort and ease. Comfortable doesn’t necessarily mean formless or invisible. Ease means you’re not fighting your clothes — not adjusting them constantly, not physically uncomfortable, not distracted by what you’re wearing. Ease is compatible with looking and feeling elevated. In fact, it’s one of the things that creates the quality of ease that reads as genuine effortlessness.
Bring one thing you love. Not one practical item. One thing you love — something that when you put it on, you feel exactly like yourself. That item does something psychological that purely functional packing doesn’t.
Allow for doing less. Especially if this trip is about rest, about recovery, about stepping back from a season that has been demanding: pack for a version of yourself that is genuinely resting. Not the productive version. Not the aspirational version. The version that is allowed to do less, want less, be less, and still deserve to look the way she wants to look.
On Confidence and Travel
There is a connection between personal confidence and how we navigate new environments that I find interesting.
When we’re in unfamiliar places — new cities, new cultures, new social contexts — the sense of being seen and the experience of being unknown can coexist in an interesting way. We have, in some sense, a clean slate. Nobody knows us here. There is a kind of freedom in that.
Some people find that freedom quietly liberating in how they dress on vacation — they’ll wear something they wouldn’t at home, try a color or silhouette that feels like too much in their everyday context, let themselves take up a little more visual space. If that’s you, I’d encourage it. Travel can be a useful place to experiment.
This connects to a broader principle I’ve written about in Styling as Self-Expression: Dressing for the Person You’re Becoming — the idea that how we dress can be a place where we try on not just clothes but possibilities.
When Vacation Style Is Also About Recovery
For many people right now, this section is the most relevant one.
If you’re packing for a trip that is partly or largely about recovery — from a hard season of work, from stress or grief, from a period of sustained depletion — the question of what to bring has an emotional dimension that pure logistics misses.
The question becomes: what do I want to wear while I let myself rest? What feels like giving myself permission to stop performing? What does rest look like in the body, including in how I dress?
Sometimes that’s your softest, most unremarkable clothes. Sometimes it’s something genuinely beautiful, because beauty is one of the things that nourishes you and you’ve been starved of it. Sometimes it’s color, because you’ve been living in neutrals and neutrals are starting to feel like camouflage.
Pay attention to that. It’s information about what your system actually needs.
Read Getting Dressed When Life Feels Heavy for more on how styling shows up in hard seasons. And if you’d like support building a travel wardrobe — or a wardrobe for any season of your life — personal styling is available to help you get there.
Vacation should feel like relief. Start packing accordingly.
