What to wear when you travel
Trips don’t have to include a meltdown the night before.
When I work with my clients, we don’t just “throw things in a suitcase.” We build intentional outfits for the exact trip they’re taking (because a family trip to Orlando does not require the same items as a work conference to Orlando.
Here’s how I approach it:
💼 Work Conference
You want: polished, comfortable, confident.
Think:
2–3 elevated tops
2 bottoms that fully mix + match
1 great topper (blazer, jacket, structured layer)
Comfortable shoes that can survive long days
Simple accessories that make everything look styled
The goal is to look like you put some thought into every outfit because a sloppy, ill-prepared person is not professional. Everything needs to work together with no random pieces. Bonus: You won’t have to panic-change before that networking dinner.
🌴 Family Vacation
You want: relaxed but still cute in photos.
Pack:
Easy tops you can re-wear
Bottoms that go with all the tops
A lightweight layer
One outfit that feels a little special
Shoes you can actually walk in
Comfort first. Style always.
🎢 Disney Trip
Function is queen.
Lightweight layers (tank + tee + hoodie)
Broken-in sneakers (please 🙏)
Hands-free bag
Hat + sunglasses
Pieces you can rotate without looking identical in every photo
We build 4–5 base pieces into multiple outfits, so you feel like yourself — even at hour 12.
My Non-Negotiable Travel Rules ☁️
Check the weather. Always.
Plan your outfits for each day before you leave.
Even if you’re re-wearing pieces.
You don’t have to follow it perfectly. But when you land, you won’t be scrambling, stressing, or “making something work.” You’ll just… get dressed.
That alone changes the whole trip.
Bonus tip! Take pictures of each outfit and label them in your phone so you know exactly what to wear each day.
If you want to see exactly how I build these travel wardrobes, you can shop my curated travel catalog here:
As always,
The JH Way
TLDR: Pack outfits, not piles of clothes. Check the weather and plan each day so you’re never scrambling when you arrive. Mix and match pieces so everything works together, and you can re-wear items with intention.
