As infrequent fliers who take maybe three trips a year, Missy and I have made just about every packing mistake in the book. The eternal struggle of overpacking vs underpacking has cost us extra baggage fees, left us shivering in unexpected weather, and created some pretty memorable (if not always pleasant) travel stories. After years of trial and error, we've finally found a middle ground that works for our travel style.
The overpacking vs underpacking dilemma is something every traveler faces, but it's especially tricky when you don't travel frequently enough to have your packing game down to a science. Unlike frequent business travelers who can pack the same essentials on autopilot, we're constantly second-guessing ourselves: "What if it rains? What if we go somewhere fancy? What if I need seven different shoe options?"
The Overpacker's Dilemma: When More Isn't Better
I'll admit it – I'm naturally an overpacker. My philosophy used to be "better safe than sorry," which translated to bringing three jackets for a four-day trip to San Diego in July. Missy still laughs about the time I packed a full suit for our casual weekend getaway to Nashville, "just in case we decided to go somewhere upscale."
Overpacking creates real problems beyond just the physical weight. We've paid those dreaded $75 overweight baggage fees more times than I care to admit. There's also the mental burden of lugging heavy suitcases through airports, up hotel stairs, and into Ubers. Not to mention the time we spent 20 minutes repacking our suitcase on the hotel bed, trying to fit in souvenirs we'd bought.
The worst overpacking incident happened on our trip to Portland last year. I brought so many "just in case" items that we couldn't fit our dirty laundry back in for the return trip. We ended up buying a cheap duffel bag at the airport and paying for an additional carry-on. That $40 lesson taught me that more isn't always better.
Here's what I've learned about avoiding the overpacking trap:
Stick to a color palette: Choose 2-3 colors that all work together. Everything mixes and matches, reducing the need for multiple outfit options.
Apply the one-week rule: Even for longer trips, pack for one week max and plan to do laundry. Most destinations have laundromats or hotel laundry services.
Question each item: Ask yourself, "Would I be willing to carry this item for an extra mile if I had to?" If the answer is no, leave it home.
The Underpacker's Regret: When Less Becomes Stress
Missy, on the other hand, is a chronic underpacker. Her minimalist approach sounds great in theory, but it's led to some uncomfortable situations. She once packed only sandals for a week in Seattle in October (spoiler alert: it rained constantly). We spent our first day buying her proper rain boots and a warm jacket instead of exploring Pike Place Market.
The underpacking mindset of "I'll just buy what I need there" can get expensive quickly. Sure, you can find basics anywhere, but you'll pay tourist prices. That $60 rain jacket we bought in Seattle would have cost $25 at home with a little planning.
Underpacking becomes particularly problematic when you're traveling to places with limited shopping options or when you have specific needs. During our Great Smoky Mountains trip, Missy realized she'd forgotten to pack any hiking socks. The small mountain town we were staying in had exactly one tiny general store, and their sock selection was... limited. She spent three days hiking in regular cotton socks and paid for it with some impressive blisters.
However, underpacking isn't all bad. There's something liberating about traveling light. Missy breezes through airports while I'm wrestling with my overstuffed roller bag. She never worries about weight limits, and her packing and unpacking takes minutes instead of hours.
Finding Your Packing Sweet Spot
After years of swinging between extremes, we've developed a system that works for our infrequent flier lifestyle. The key to solving the overpacking vs underpacking challenge is creating a repeatable process that you can rely on, even when you're only packing a few times a year.
Create a master packing list: We keep a shared Google Doc with categories for different trip types (beach, city, mountains, international). This prevents us from forgetting essentials while also providing a reality check on quantities. When I see "7 t-shirts for 4-day trip" written out, it's easier to cut it down to a reasonable number.
Use the "5-4-3-2-1" rule for week-long trips: 5 sets of underwear and socks, 4 tops, 3 bottoms, 2 jackets/layers, 1 dress-up outfit. Adjust ratios based on your trip, but this gives you a starting framework.
Invest in versatile, quality pieces: A merino wool cardigan works as sleepwear, a layer for air conditioning, or a light jacket. A good pair of walking shoes can work for casual dinners too. We love our Allbirds Tree Runners – they're comfortable for all-day walking but don't look like obvious tourist shoes.
Pack one "just in case" item each: This satisfies the overpacker's anxiety while keeping things reasonable. I might bring one extra nice shirt; Missy might pack a light scarf that could dress up an outfit or provide warmth.
Check the weather twice: Once when you start planning, and again 2-3 days before departure. Weather can change, but this helps avoid bringing shorts to a cold snap or forgetting rain gear for an unexpected storm.
Consider packing cubes: We swear by our Eagle Creek packing cubes. They keep everything organized and make it easy to see how much you're actually bringing. Plus, they compress clothes efficiently, giving you more room without adding weight.
The overpacking vs underpacking balance is personal and depends on your travel style, destination, and comfort level. As infrequent fliers, we've learned that the perfect packing formula is less about having the right amount of stuff and more about bringing the right stuff. A thoughtful selection of versatile, quality items beats a random assortment of everything you might possibly need.
The Bottom Line: Start with a list, pack for one week maximum, choose versatile pieces in a coordinated color scheme, and give yourself one "just in case" item for peace of mind. Your back (and your wallet) will thank you, and you'll spend more time enjoying your destination instead of managing your luggage.