5 Packing Errors That Can Wreck a Trip and 5 Guidelines That I Stand By

      Monica Mendal serves as an editor in residence at Who What Wear, has previously worked as a fashion editor, is a travel writer, and authors the Substack newsletter So There's This Place…, where she shares curated guides, insider tips, and unique travel destinations. Packing for a trip involves more than just remembering your chargers and adapters—trust me. Many things can go awry—like that time I ended up packing only two pairs of pants for an entire month in Greece. No, don’t ask how that happened. Sure, there are the common tips everyone knows (such as putting shoes in first, rolling soft items, and folding structured ones), but I've also picked up several straightforward strategies over the years as a travel editor who boards a flight every week. Packing for travel often feels like a precarious balancing act. Bring too little, and you'll find yourself in a lurch for essentials; bring too much, and you'll be lugging around an oversized suitcase. Over time, I've realized that it's not solely about what you bring but also about how you pack. A few minor errors can swiftly turn a dream vacation into a stressful ordeal, leading to blisters, motion sickness, or a suitcase that won't close. Below are the most frequent packing errors I've noticed in my travel companions, along with my go-to tips to ensure my trips run smoothly, stay organized, and remain stress-free.

      Mistake #1: Hiding Your Essentials on Travel Day

      Scrambling for your passport, boarding pass, or phone while at security or boarding can quickly start your trip off on the wrong foot.

      Rule: Keep a small crossbody bag or pouch with everything you need within easy reach. Your passport, boarding pass, phone, and AirPods should all be kept in one accessible location. Bonus: It allows your hands to be free for coffee, snacks, or a magazine.

      Mistake #2: Overpacking Single-Use Items

      That adorable top that only pairs with one specific pair of pants? It will lead you to feel like you have "nothing to wear," even when your suitcase is full.

      Rule: Pack in systems rather than outfits. Select tops and bottoms in versatile neutrals that can be mixed and matched, along with a few adaptable layers—like a light jacket, cashmere sweater, and travel wrap—that work with everything. Packing cubes can be incredibly helpful; use them to organize by category instead of by outfit: one cube for gym clothes, another for swim gear, one for bottoms, tops, etc. You can include one fun "just because" item, but the rest should serve multiple functions.

      Mistake #3: Neglecting Your Shoe Strategy

      Shoes occupy the most space, so it's crucial to be very selective here. Comfort is key! Traveling is not the time to break in a new pair, as you'll want to avoid blisters from new shoes on your first day.

      Rule: Only bring versatile, already broken-in shoes. Choose pairs that complement every outfit, can withstand a bit of rain, and transition effortlessly from day to evening. Classic Mary Janes, soft loafers (or lightweight ankle boots), and comfortable sneakers for travel days are essential. Ensure all your shoes are well broken in before your trip.

      Mistake #4: Overlooking an Emergency Kit

      A sudden headache, an upset stomach, seasickness on a rocky ferry, or blistered feet can ruin a day—especially when the nearest pharmacy is far away or closed on a Sunday in Italy.

      Rule: Pack a mini emergency kit for every trip, including essentials like ibuprofen, stomach relief, hair ties, fashion tape, a Tide pen, safety pins, blister patches, and toothpaste. It's a major stress reliever. Also, have an additional tech organizer with chargers, USB cords, and adapters at hand.

      Mistake #5: Filling Your Suitcase Completely Before Departing

      Leaving no extra space means there's no room for souvenirs, market finds, and those spontaneous shopping treats that make a trip special.

      Rule: Intentionally leave about 15% of your suitcase empty. Extra space provides flexibility, peace of mind, and room for all the little treasures you acquire along the way. If you don't take this advice, at least consider investing in an expandable suitcase or travel bag!