The precise moment I knew I had a problem was standing in the security line at O’Hare, watching a family of four check fewer bags than I had packed for a solo long weekend in Miami. The father—efficiently dressed in performance chinos and one of those travel shirts with hidden pockets for your passport—glanced at my overstuffed roller bag and sizeable “personal item” tote with what I can only describe as pity. His wife was somehow bringing just one tasteful, compact duffel for herself and both children, while I had packed like I was fleeing the country with the crown jewels.
I’d like to tell you this was an unusual occurrence. That I’m actually a minimalist packer who ruthlessly edits his vacation wardrobe to the bare essentials. But the truth is, I have historically approached packing with the philosophy that it’s better to have options. Too many options. Options for weather that the forecast doesn’t predict, for impromptu formal events that might spontaneously materialize, for the possibility that I might suddenly develop an entirely new personal style mid-trip.
It’s ridiculous, I know. The reality is I end up wearing maybe 40% of what I pack, lugging the rest around like some kind of fashion security blanket. Meanwhile, my girlfriend can pack for a two-week European vacation in a bag that fits under the seat, containing a wardrobe that somehow looks freshly pressed and appropriately on-point for every single activity and setting. It’s witchcraft, honestly.
The breaking point came last year when airlines somehow made their already draconian baggage policies even more restrictive. Suddenly, my strategy of “I’ll just pay for a checked bag” didn’t seem so clever when that bag now cost almost as much as the flight itself. Add in the indignity of waiting 45 minutes at baggage claim (if your luggage shows up at all) while all the smart carry-on people are already halfway to their destinations, and I knew something had to change.
So I embarked on what my friends now call “The Great Packing Reformation”—a complete overhaul of how I approach vacation wardrobes. Through extensive trial and error (and several embarrassing over-packing incidents), I’ve developed a system that lets me pack for up to a week in just a regulation carry-on, with clothes that actually work together and accommodate most situations a normal human might encounter. No more bringing four pairs of shoes “just in case.” No more packing three sport coats for a beach vacation (yes, I really did this once).
The foundation of efficient packing is brutal honesty about what you’ll actually be doing on vacation. Not what you imagine you might do in some alternate-universe version of your trip where you’re suddenly invited to dine with local aristocracy, but what you will realistically be doing based on your itinerary, destination, and—most importantly—your actual habits.
For years, I packed aspirationally rather than realistically. I’d bring running shoes and workout clothes for a trip where my only planned exercise was lifting cocktails to my mouth. I’d pack blazers and dress shirts for beach destinations where the fanciest restaurant still allowed flip-flops. I was packing for some imaginary version of myself who suddenly develops habits and preferences completely different from my normal life just because I’ve crossed state lines.
The first step in my reformation was creating what I call a “reality check” list before any trip. It forces me to map out what I’ll actually be doing each day and night, with specific attention to dress codes and activities. Beach day? Museum visit? Nice dinner? Casual drinks? Hike? Work meeting? Once I have this honest assessment, I can build a wardrobe that covers these actual needs rather than hypothetical scenarios.
This might seem obvious, but I can’t tell you how many men I know who pack with a vague sense of “well, you never know what might happen” rather than looking at what’s actually on the schedule. Trust me, if you unexpectedly get invited to a formal gala in Barcelona, you can either buy something there (shopping in a new city is part of the fun!) or politely decline. The possibility doesn’t justify hauling a tuxedo across the Atlantic.
The next foundation of carry-on success is embracing the reality of doing laundry on the road. I know, I know—laundry on vacation feels like defeat. But modern quick-dry fabrics and the ubiquity of hotel laundry services (or even just a bathroom sink and some travel detergent) mean you can bring half as much and just wash key items halfway through. I now pack assuming I’ll do at least one small load of laundry on any trip longer than four days.
This was a psychological hurdle for me. Something about planning to do laundry felt like I was somehow “failing” at vacation. But once I embraced it, my luggage literally halved in size. Instead of seven t-shirts for a week-long trip, I bring three or four high-quality ones that can be washed in a hotel sink and dry overnight. The fifteen minutes it takes to wash a few key items is far less painful than dragging an oversized checked bag through crowded streets or paying excess baggage fees.
With those foundations in place, let’s talk about the actual strategy of building a vacation wardrobe that fits in a standard carry-on while still giving you enough flexibility to look and feel good throughout your trip.
The most crucial concept is the color palette. Before I pack a single item, I now decide on a limited color scheme—usually no more than three core colors plus one or two accents. This ensures that virtually everything in my bag works with everything else, creating exponentially more outfits from fewer pieces.
For a recent week in Portugal, I built everything around navy, olive green, and white/cream, with burgundy as an accent. Every single item I packed—from t-shirts to shorts to the one light jacket—fit within this palette. The result was being able to get dressed in seconds each morning, knowing that any combination would work together visually. No more staring at an open suitcase full of clothes that somehow don’t go with anything else I’ve brought.
This approach requires discipline. That statement piece with the bold pattern might be amazing, but if it doesn’t work with at least three other items in your bag, it’s staying home. Save those one-off outfits for when you’re not living out of a suitcase. Vacation is when versatility becomes your best friend.
Next comes the brutal math of multi-functionality. Every single item in your carry-on should serve at least two purposes or work in at least two distinct settings. That linen button-up isn’t just for dinner—it’s also a beach cover-up. Those chino shorts work for daytime sightseeing but can handle an evening out with the right shirt. The lightweight sweater layers under your jacket for cooler evenings but works on its own during the day.
When I’m debating whether to pack something, I now ask myself: “What are the specific scenarios where I’ll wear this?” If I can only name one occasion, it doesn’t make the cut. This rule alone has probably saved me from bringing dozens of “just in case” items that would have spent the entire vacation compressed at the bottom of my bag.
The shoes question is where most men’s packing falls apart. I used to be a four-pair-minimum guy: sneakers for walking, loafers for casual evenings, dress shoes for nice dinners, and maybe boat shoes or sandals for beach days. That’s literally half your carry-on space just for footwear. Now I aim for two pairs, three absolute maximum.
For most trips, I’ve found that one pair of minimal, comfortable sneakers (think plain white leather that can dress up or down) and one pair of versatile loafers or driving shoes cover 95% of vacation scenarios. For beach trips, I’ll add flip-flops, which take up virtually no space. The key is choosing shoes that bridge dress codes—those crisp white sneakers can handle a museum day but also work with chinos for dinner. The loafers dress up with a button-down for evening but don’t look fussy with shorts during the day.
This approach requires letting go of strict formal/casual distinctions that matter more at home than on vacation anyway. Most vacation destinations (outside of business trips) have more relaxed dress codes than you might assume. That fancy restaurant in Positano is probably full of people wearing clean sneakers with their linen shirts. The rooftop bar in Barcelona isn’t expecting wingtips. Pack for the reality of your destination, not the formality of your hometown.
The fabric question is another game-changer for efficient packing. I’ve gradually replaced many of my vacation clothes with versions in wrinkle-resistant, quick-drying, and in some cases, odor-resistant technical fabrics. Not the obvious “I’m wearing performance gear” kind, but the new generation of technical fabrics that look like normal cotton, linen, or wool but perform much better on the road.
Brands like Lululemon, Ministry of Supply, and Proof now make shirts, pants, and even blazers that can handle being rolled up in a suitcase, worn multiple times, and even given a quick sink wash if needed. They might cost more initially, but they’ve transformed my packing strategy by giving me more wears per item with less maintenance. My favorite travel button-up looks like Oxford cloth but dries in a third of the time and emerges from my bag without needing ironing.
And since we’re talking about fabric, let’s address the rolling versus folding debate. After extensive experimentation, I’ve found that a hybrid approach works best. Thinner items like t-shirts, underwear, and swimwear get rolled tightly. Button-ups and pants get folded along their natural seams and laid flat. Jackets, if I bring them, get turned inside out, folded once, and placed on top. This maximizes space while minimizing hard creases.
For a standard week-long vacation in a temperate climate, my carry-on now typically contains: three t-shirts, two button-ups, one light sweater or long-sleeve tee, one pair of jeans or trousers, two pairs of shorts, one pair of swim trunks (that can double as casual shorts), five pairs of socks and underwear, two pairs of shoes, and possibly one light jacket depending on the forecast. Everything works together colorwise, and most items serve multiple functions.
That might sound minimalist, but it’s more than enough for a week when you consider that you’ll be wearing one complete outfit while traveling, leaving only six days to cover from your bag. With mix-and-matching and perhaps one quick load of laundry midweek, this creates plenty of options without hauling half your closet across the country.
Let’s talk about the toiletry situation, which can quickly consume valuable carry-on space if you’re not careful. I’ve ditched most of my full-size products in favor of either travel sizes or solid versions—solid cologne, shampoo bars, and deodorant all take up less space and eliminate liquid concerns for TSA. I also no longer bring “just in case” toiletries for scenarios I’m unlikely to encounter. Most hotels provide the basics, and anything else can be purchased at your destination if truly needed.
My dopp kit used to be the size of a small briefcase. Now it’s a compact pouch containing only what I know I’ll use daily. The space savings is significant, and I’ve yet to encounter a toiletry emergency that couldn’t be solved with a quick stop at a local pharmacy. Does anyone really need three types of hair product on vacation anyway? (My answer used to be yes, embarrassingly.)
A word about outerwear, which can be the carry-on killer. For most trips, I now wear whatever is bulkiest on the plane—be it a light jacket, sweater, or both. This not only saves suitcase space but also gives me layers to adjust to often-frigid airplane cabins. If I absolutely need a heavier coat for the destination, I’ll wear it while traveling even if it means being slightly overdressed at the departure airport. Better that than sacrificing half your luggage space.
For cold-weather destinations, I’ve embraced the technical advantages of modern lightweight down and synthetic insulation. My winter travel jacket packs down to the size of a water bottle but provides serious warmth. It’s not what I’d choose for style points at home, but for travel, the space savings is worth the minor aesthetic compromise. And honestly, newer technical outerwear has come a long way in the looks department.
Here’s a travel hack that’s saved me repeatedly: pack one simple, fool-proof outfit that makes you feel great right in the top of your suitcase. Something that requires zero thought and works for most situations. This becomes your emergency outfit for when laundry plans fall through, when unexpected weather hits, or when you’re just too tired to think about what to wear. Mine is usually dark jeans, a navy button-up, and clean white sneakers—basic but put-together enough for most scenarios.
This brings me to my most controversial packing opinion: it’s better to slightly underpack than overpack. If you find yourself short an item, you can almost always purchase it at your destination—and often, that locally purchased piece becomes a unique souvenir with an actual story behind it. Some of my favorite items of clothing came from vacation shopping emergencies: the linen shirt bought in Lisbon when an unexpected heatwave hit, the sweater from a small shop in Copenhagen when I underestimated the evening chill.
Contrast this with the psychological weight of dragging around excess clothing you never wear. I’d rather spend twenty minutes and fifty bucks buying an extra t-shirt locally than haul four “just in case” shirts across the globe and back untouched. The math on this just makes sense, both financially and in terms of travel enjoyment.
So what does this all look like in practice? Let me break down my actual packing list for a recent seven-day trip to Italy in late spring, all of which fit in a standard carry-on plus a small backpack:
In my carry-on: Two short-sleeve button-ups (one olive, one subtle pattern with navy/white), two t-shirts (one white, one burgundy), one long-sleeve henley (navy), one pair of jeans (dark blue), one pair of chino shorts (olive), one pair of swim trunks that double as casual shorts (navy), one lightweight quarter-zip sweater (navy), five pairs of underwear, three pairs of socks, one pair of loafers (brown), toiletry kit, and one packable rain jacket just in case.
Worn on the plane: Minimal white sneakers, light blue button-up shirt, comfortable chinos in a stone color, watch, belt.
That’s it. Everything worked with everything else. I did one small sink wash of t-shirts and underwear halfway through. I felt appropriately dressed for every situation, from casual pizzerias to a surprisingly upscale vineyard tour. And most importantly, I never had to check my bag, roll it over cobblestone streets, or hoist it onto crowded trains.
The greatest luxury in travel isn’t bringing your entire wardrobe—it’s the freedom of movement that comes with packing light without sacrificing style. It’s breezing past the baggage claim while the checked-bag people wait in purgatory. It’s easily navigating public transit instead of requiring taxis due to unwieldy luggage. It’s the physical and mental lightness that comes from carrying only what you actually need.
My girlfriend, who has always been a packing minimalist, watched my transformation with amusement. “Welcome to the light side,” she said as I proudly displayed my single carry-on before our last trip. “Only took you what, fifteen years of overpacking?”
She’s not wrong. But I like to think all those years of bringing too much have given me a unique appreciation for bringing just enough. And if I occasionally find myself short an item? Well, that’s just an opportunity to bring home something new with an actual travel story attached to it—which beats another unworn shirt that spent its vacation in the dark confines of an overstuffed suitcase any day.
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