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How many times have you gone on a trip, spent so much time packing, only to arrive and wonder how you could have possibly missed a key piece of clothing—or worse, realized nothing you brought actually works together?
I’ve been there more times than I can count. I used to frustrate myself wearing uncomfortable shoes that didn’t match, or running to buy something last minute that cost way more than I wanted to spend.
Finally, I told myself I wouldn’t be unprepared again. That’s when I came up with a simple outfit planning system using my trusted partner, Apple Notes. (Of course, you can use whatever tool works best for you!) Now, packing is less stressful, actually kind of fun, and I usually wear everything I bring.
Here’s my step-by-step guide on how to plan outfits for any trip—leisure, business, or otherwise—with real examples from my upcoming trip to Italy (next week!!!).
👉 Also see: Essential Tips for Efficient Carry-On Packing
Step 1: List Your Plans
Outfit planning starts with knowing what you’re planning around. Open a blank note and list your trip by day. Under each day, jot down your itinerary (and get excited!). For example:
- “Boat day: outfit”
- “Exploring the town: outfit”
- “Dinner by the water: outfit”
Even if it feels small—like swapping into something fresh for dinner after sightseeing—write it down. And don’t forget the weather! A rainy-day hike calls for different shoes than an evening rooftop dinner.
(For my trips, I actually keep a completely separate note for my detailed itineraries—more on that in another post!)
Step 2: Shop Your Closet First
Next, sit in your closet with your list and start pulling items. Don’t start on Pinterest—you’ll only end up wanting that exact piece you see (yea…ask me how I know!) and buying something new that ends up in the donation pile a few months later.
Instead, build from what you already own. Personally, I have plenty of clothes just waiting for a fun destination.
Start with a few pieces you love or that mix and match easily, then assign them to your trip plans. For example:
- “Boat day: white linen top”
- “Fancy dinner: navy dress”
Suddenly, you’ll see the vibe forming for each day—whether casual, elevated, or a mix of both.
Step 3: Fill in the Gaps
If there’s something you just can’t pull together from your closet, then (and only then): shop. Check thrift stores, your favorite go-to brands, or online.
Be intentional—choose items you’ll wear at home too, not just on vacation.
✨ Pro tip: Keep your color palette tight—2–3 neutrals plus 1–2 accents—so everything mixes and matches if plans change.
Step 4: Write It All Down (or Snap a Pic!)
Once you’ve chosen your outfits, record them in detail. I usually do it like this:
- Boat day: white linen top, navy shorts, brown sandals, straw hat
- Dinner: navy dress, gold hoops, block heels
Some people prefer to lay everything out, snap a picture, and drop it into their notes app. Do whichever works for you!
You also don’t have to know everything right off the bat. This process usually takes me a few days to complete every outfit.
Bonus: this doubles as a reference during the trip. No standing in front of your suitcase in the morning wondering what to wear—you already decided.
Step 5: Make Your Packing List
Turn your outfits into a checklist of individual items. Be thorough! The right earrings, belt, or bag can make an outfit feel finished, and it’s easy to forget them when you’re rushing to pack.
I also like to note which items I’ll be wearing on the plane so I don’t accidentally pack them.
Confession: sometimes I skip this step and just cross-check outfits while packing… a little riskier, but hey, I like to live on the edge 😎.
Step 6: Edit for Efficiency
Finally, edit your list with luggage space in mind. Especially if you’re packing a carry-on (see my carry-on tips here).
- Two pairs of sandals? Maybe one pair works for both outfits.
- Three dresses? Narrow to two and re-wear one.
The goal is to save space while still feeling stylish and prepared.
Step 7: Get to Packing
Okay—maybe not the most fun part, but this is where all your planning pays off. With a solid outfit plan and a few smart packing hacks, you’ll be surprised how much you can fit in a carry-on suitcase or backpack without feeling like you left anything behind. Packing cubes are a game-changer here—they make everything slot into place faster, keep items organized, and help you fit more into the same space.
I’ll be sharing some of my Italy packing process over on Instagram—follow along if you want to see it in action!
Final Thoughts
This system has completely changed the way I pack. On our honeymoon in Honduras, I knew exactly what to wear for each dinner, pool day, and outing. It felt so good not to scramble last minute.
And I know next week, when I’m standing on a boat in Cinque Terre in that white linen top, I’ll be so glad I did this prep now.
✨ Pro tip: Always pack one “confidence outfit”—the one that makes you feel your best. You never know when a surprise photo op or special dinner will pop up!
How do you plan your outfits for trips? Do you wing it or plan every detail ahead of time? Let me know in the comments—I’d love to hear your tips too.
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