5 Packing Mistakes That Can Ruin a Trip and 5 Rules That I Swear By
Monica Mendal is a Who What Wear editor in residence, a former fashion editor, a travel writer, and the author of So There's This Place…—a Substack newsletter where she shares curated guides, insider tips, and off-the-beaten-path destinations.
Packing for a trip is about more than just remembering your adapters and chargers. Believe me. A lot can go wrong—like the time I somehow managed to pack only two pairs of pants for an entire month in Greece. Don't ask me how that happened. Sure, there are the basic tips everyone knows (like shoes go in first, roll soft items, fold structured ones), but beyond that, there are a handful of simple strategies I've learned over the years as a travel editor who boards a flight every week.
Packing for a trip can feel like a delicate balancing act. Bring too little and you'll be scrambling for essentials. Bring too much and you're dragging around a suitcase twice your size. Over the years, I've learned that it's not just about what you pack. It's how you pack. A few small mistakes can quickly turn a dream getaway into a stressful experience, from blisters and motion sickness to a suitcase that refuses to close. Below are the most common packing pitfalls I've seen my travel companions make and the pro tips I swear by to keep my trips smooth, organized, and stress-free.
Mistake #1: Burying Your Essentials on Travel Day
Scrambling for your passport, boarding pass, or phone at security or boarding is the fastest way to start a trip frazzled.
Rule: Keep a small crossbody or pouch for everything you need within arm's reach.
Passport, boarding pass, phone, AirPods—everything that matters in one easy-access spot. Bonus: It keeps your hands free for coffee, snacks, or a magazine.
COS
Trove Crossbody Bag in Leather
Sézane
Heritage Victor Bag
& Other Stories
Small Leather Crossbody Bag
Mistake #2: Packing Too Many Single-Use Pieces
That cute top that only works with one specific pair of pants? It'll make you feel like you have "nothing to wear" even though your suitcase is overflowing.
Rule: Pack in systems, not outfits.
Choose tops and bottoms in enough neutrals that mix and match and a few versatile layers—like a light jacket, cashmere sweater, and travel wrap—that work over everything. Packing cubes are your best friend. Use them to organize by category, not by outfit: one cube for gym gear, one for swimwear, one for bottoms, tops, etc. Yes, you're allowed one fun "just because" item, but everything else should serve multiple purposes.
