There’s a moment that you’ve all had. You look around and realise that for however long you’ve been doing whatever you’re currently doing, you’ve been doing it wrong. Mine came to me during a particularly frustrating security line at O’Hare.
I was standing behind this family of four that made me look embarrassingly messy by comparison. The father had one streamlined roller bag and was wearing travel trousers that had like seven different zip pockets. His wife had managed to pack for herself and their twin girls all within a weekend-sized duffel bag.
And me? I’m awkwardly stuffing my monstrous roller bag and “personal item” that looked more like a small suitcase into two overhead bin compartments and hoping the gate agent doesn’t make me cheque a bag.
This was for a long weekend trip to Miami.
Three days. I mean, I got laid off packing like I was going to live there forever or that my closest friends were hosting some kind of 17th century pirate-themed emergency. There’s something humiliating about admitting that this wasn’t even an abnormal amount of stuff for me.
I’m the type of person who always likes options. Too many options when packing for holiday. Options for unpredictable weather, options for events I know I probably won’t attend, options for in-case-I suddenly-develop-entirely-different-style-taste halfway-through-the-plane-ride.
I wish I could say that was the wake-up call I needed to thin out my packing strategy, but I’d continued to stuff baggage bins with enough clothes to relocate the average family of three for about six more trips before I truly took stock of my problem. My girlfriend can pack for two weeks abroad in Europe in a carry-on sized bag and still look put-together for every activity. Meanwhile I show up with three damn sport coats on a beach holiday (true story) and still can’t find anything to wear.
Ahem. The real straw that broke the carry-on camel’s back, however, came when airlines decided that $50 wasn’t enough to dissuade people from checking bags. Now I was paying almost as much to cheque my bag as I paid for my ticket only to sit at baggage claim for 45 minutes watching all of the savvy carry-on folk jet off to begin their holidays while I anxiously hoped my bag was within five miles of my own location.
Something had to change. I decided that my next holiday was going to be the beginning of a whole new way of travelling light. My friends lovingly (?) dubbed it “The Great Packing Reformation.” Dramatic?
Sure. But it stuck and whatever. After years of unnecessary overpacking – which still happens from time to time, we’ve all got our guilty sins – I’ve honed my craft to the point where I can pack for up to a week away in just a carry-on bag.
And look presentable doing it, too. No more waking up in hotels hungover and hoping that whatever I grab will at least not attractattention-or-make-it-seem-like-I-peed-myself. The first step was being honest with myself about what I would ACTUALLY be doing on holiday.
Not the version of holiday where you randomly get invited to embassy events and pop-up yacht parties, but the real itinerary you’ll actually be following. And more importantly, the real you that will be following that itinerary. For too long I packed with aspirational activities in mind.
Golf clubs on trips where I planned on doing absolutely no exercising besides maybe picking up my drink from the bar. Blazer and slacks combinations on beach holidays where the only restaurant that allowed trousers still didn’t care if you wore sandals. I was packing like I was someone who randomly decides to live by a completely different set of hobbies and activities just because he changes ZIP codes.
News flash- if I’m not suddenly dying to go for morning jogs just because I’m visiting Chicago I’m probably not going to turn into a cardio beast when I travel to Cancun. <img class=”size-full” src=”http: //joewears.co.uk/wp-content/uploads/2025/04/im1979_Building_a_Vacation_Wardrobe_That_Actually_Fits_in_a_C.jpg” alt=”im1979_Building_a_Vacation_Wardrobe_That_Actually_Fits_in_a_C” />Plus, I was leaving no stone unprepared. See, the thing with packing everything but the kitchen sink is that you kinda have to pack a kitchen sink. It adds up.
I found that once I started planning around things I would definitely do on holiday vs. everything I possibly could that I not only got WAY less, but what I did bring <a href=”https: //joewears.co.uk/building-a-wardrobe-that-works-for-lasting-sexy-versus-you-only-live-once/” data-wpil-monitor-id=”17″>actually worked together and didn’t make me look like a hot mess</a>. I’m sure this sounds like common sense to most of you, but trust me, there are people out there who pack for every single contingency. “What if we get invited to that new French place for dinner?” You’ll either buy a shirt there (it’s kind of fun actually) or decline. But sweating through your shirt because you “just in case packed” something dressier is not a classy look on anyone.
Accepting that I would (and likely would need to) do laundry abroad was another mental hurdle for me. Like, who wants to spend their holiday doing laundry? ADULTS.
Adults do laundry on holiday, so they can pack half as much stuff and simply wash whatever they were wearing halfway through the trip. It’s a beautiful thing. Also, laundry detergents and travel sized shampoo are usually squirts rather than litters so they don’t take up much space. <img class=”size-full” src=”http: //joewears.co.uk/wp-content/uploads/2025/04/im1979_Building_a_Vacation_Wardrobe_That_Actually_Fits_in_a_Cdd3f1c33-82c0-40b3-8b44-1a0a8f8b994d_-1.jpg” alt=”im1979_Building_a_Vacation_Wardrobe_That_Actually_Fits_in_a_Cdd3f1c33-82c0-40b3-8b44-1a0a8f8b994d_” />When you travel with fabrics that are specifically made to be wrinkle-, quick-, and sometimes even odor-resistant, doing laundry on holiday isn’t the sweaty hellshower you’re envisioning in your head right now.
Plus, most accommodations will have you laundry options whether that’s through an in-house laundry service or at the very least access to a bathroom sink. So you can wash that white shirt and hang it over your shower curtain to dry overnight. That mental “ugh” I associate with doing laundry somehow translated into my whole packing process.
Who wants to waste time packing if I’m just going to have to spend more time unpacking and washing it all again halfway through?! Am I right?!?? But once I got over this ridiculous mental hurdle, my bag size cut in half.
Instead of packing 7 t-shirts “just in case” I land somewhere warm, I bring 3 or 4 good ones that can be rinsed out in the sink and laid out to dry overnight. Same thing with jeans, shorts, even jackets. Those 15 minutes you spend washing a few essential items is NOTHING compared to the headache of hauling around an overweight suitcase through busy airports or paying these fucked baggage fees.
Ok so that’s all great but how do you actually pack like that?!? C’mon Joe. Spill your secrets.
Well the foundation of any well packed carry-on is planning your wardrobe around a limited colour palette. Literally every piece of clothing that I pack is built around ~three~ colours. Two or three main colours and then maybe an accent or two.
By forcing myself to only pack things that can coordinate with at least three other things in my bag, I not only ensure that every outfit combination looks intentional, but I can exponentially increase my outfit options with less pieces. For a recent week-long trip to Portugal I built my whole wardrobe around navy, olive green, and white/cream with the addition of burgundy as an accent colour. Every t-shirt, short, and yes… even the one light jacket I ended up actually using could be worn with any combination of these colours.
Which is helpful because come morning, I can grab anything off my hung-up clothes and know that I’ll look put together when I throw it on. Instead of stressing about what I’ll wear each day I’ve got time to enjoy my damn holiday. <img class=”size-full” src=”http: //joewears.co.uk/wp-content/uploads/2025/04/im1979_Building_a_Vacation_Wardrobe_That_Actually_Fits_in_a_Cdd3f1c33-82c0-40b3-8b44-1a0a8f8b994d_-2.jpg” alt=”im1979_Building_a_Vacation_Wardrobe_That_Actually_Fits_in_a_Cdd3f1c33-82c0-40b3-8b44-1a0a8f8b994d_” />White shirts, olive trousers, brown shoes. Done and done.
Don’t get me wrong, I have clothes with patterns and brighter colours than brown. However, if that shirt doesn’t match at least three other things in your luggage, it doesn’t get to come with. Period.
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End of discussion. It can be sunny somewhere else. When you’re restricted to a carry-on you quickly learn that versatility is king.
You might not wear that bright floral shirt often back home but if it doesn’t go with at least half your packing list, leave it at home! This brings me to the logistics of packing versatile clothing. Literally every article of clothing I pack MUST be able to serve double duty and be worn in at least two different scenarios.
That linen shirt isn’t just for dinner, it’s your beach cover-up. Those chino shorts are great for walking around all day but pair well with short sleeves for an evening drink. That lightweight jumper not only layers well under your jacket on cooler nights, but works as a standalone top during the day.
If I’m pondering about whether or not I should pack something, I ask myself “When will I actually wear this?” and “Where will I wear this?” If the answer is “maybe” or “ nowhere specific,” then that item doesn’t get packed. I used to throw in a fancy jumper here, a trendy blouse there “just in case.” Guess where those things ended up for the majority of my trips? Bottom of my duffle bag mocking me while I wore the same three outfits on rotation. <img class=”size-full” src=”http: //joewears.co.uk/wp-content/uploads/2025/04/im1979_Building_a_Vacation_Wardrobe_That_Fits_in_a_Carry-on_dd3f1c33-82c0-40b3-8b45-1a0a91f8b901_0.jpg” alt=”im1979_Building_a_Vacation_Wardrobe_That_Fits_in_a_Carry-on_dd3f1c33-82c0-40b3-8b45-1a0a91f8b901_0″ />Shoes are where most guys go completely off the deep end with packing.
I used to live by the rule of four: trainers to walk around the city, loafers for casual night time outings, dress shoes because “what if,” and then flip flops sandals for beach/hotel antics. That right there is HALF your luggage devoted to shoes. SHIT SMARTS. <img class=”size-full” src=”http: //joewears.co.uk/wp-content/uploads/2025/04/im1979_Building_a_Vacation_Wardrobe_That_Actually_Fits_in_a_C_025c0d96-8ec2-4708-aef7-42782b8d18ba_1.jpg” alt=”im1979_Building_a_Vacation_Wardrobe_That_Actually_Fits_in_a_C_025c0d96-8ec2-4708-aef7-42782b8d18ba_1″ />Now I try to limit myself to two, three max.
Sure, you may need all those shoes back home but when I’m carefully picking out which underwear to squeeze into my bag, every little inch counts. For most trips I’ve found one pair of clean, minimalist trainers and one pair of versatile loafers can cover about 90% of what you’ll come across. Wear those trainers with chinos for dinner or your favourite shorts around town.
Pair those loafers with jeans and a t-shirt for casual or under a button up for night time dining. The white sneaks can be dressed up enough to walk around most museum galleries and still won’t look sloppy with your beachwear. Eliminating the at-home formal vs. casual divide is a total game changer when packing.
You don’t need to, or should I say, rarely will you wear ultra dress clothes on holiday. Don’t get me wrong, if you’re hopping around the Italian Riviera or spending your days exploring the Spanish Riviera you’ll find plenty of upscale restaurants to fill that much needed ‘dressy’ slot in your brain. But my point is that you’re likely over estimating the dress codes of your travel destinations.
Yes, that fancy restaurant in Italy may have a “no trainers” policy but they’ll all be wearing them too. And that rooftop bar in Spain with the amazing people watching is not going to care if your shoes aren’t wingtips. Last but certainly not least, invest in the right fabrics.
This is something I’ve been slowly making peace with over the past few years. Travel clothes that can resist wrinkles, dry in half the time, and yes… even resist odors (hello sweaty flight!) have truly changed my packing game. And don’t worry, I’m not suggesting you wear “ workout clothes ” to dinner.
I’m talking about the new breed of wrinkle-free fabrics that are cut and styled to LOOK like your favourite cotton shirt or linen trousers but wear WAY nicer when you’re living out of a suitcase. Brands like Lululemon and Ministry of Supply have been killing it in the travel wardrobe department. They make lightweight shirts and trousers that can be rolled up in your bag for days, worn several times in a row, and if you’re anything like me- washed in the sink and hung to dry overnight.
They’re a bit pricier than your average trip to Uniqlo but will revolutionize your packing strategy by allowing you exponentially more wears per item with basically zero maintenance. The breathable athletic fabric of my favourite travel friendly button-up looks JUST LIKE an oxford cloth shirt but dries ⅓ as long as regular shirts and comes out of my bag not creased at all. <img class=”size-full” src=”http: //joewears.co.uk/wp-content/uploads/2025/04/im1979_Building_a_Vacation_Wardrobe_That_Actually_Fits_in_a_C_025c0d96-8ec2-4708-aef7-42782b8d18ba_2.jpg” alt=”im1979_Building_a_Vacation_Wardrobe_That_Actually_Fits_in_a_C_025c0d96-8ec2-4708-aef7-42782b8d18ba_2″ />Ok so you’ve planned out your versatile wardrobe and picked the right fabrics. How should you actually pack it all!?
By rolling vs. folding, duh. Ok, sort of. After many a trial and crash and burn I’ve developed a healthy medium that allows me to maximise space but keep things from looking like hell once I start unpacking.
Roll everything thin. T-shirts, underwear, socks, swimsuits, you name it. Fold larger items like button ups and trousers along the natural creases and lay them flat.
Jackets, if you’re foolish enough to bring one, get turned inside out, folded in half, and stuffed on top. This is by far the best way that I’ve found to pack everything tightly without everything looking like a homeless person slept in it. Ok, so what DOES my ideal carry on look like when it’s packed for holiday?
For a typical week long trip in good weather I’m packing: – 3 T-Shirts – 2 Button Ups – 1 Light Jumper – 1 Pair of Jeans – 2 Pair of Shorts – Swimsuit (that doubles as casual shorts) – 5 Pair of Socks – 5 Pair of Underwear – Shoes x2 – Light Jacket (weather dependent) Almost everything matches colour wise and every item can be worn in at least 2 different scenarios. Sure that sounds like A LOT of clothes, but remember you’ll be wearing one whole outfit on the way down so you technically only have to pull from your bag for six days worth of clothes. And when you factor in mix and matching plus that mid-week laundry session, you’ve got plenty of outfits to last your entire trip without trying to fit your entire closet into your luggage. <img class=”size-full” src=”http://joewears.co.uk/wp-content/uploads/2025/04/im1979_Building_a_Vacation_Wardrobe_That_Actually_Fits_in_a_C_025c0d96-8ec2-4708-aef7-42782b81_3.jpg” alt=”im1979_Building_a_Vacation_Wardrobe_That_Actually_Fits_in_a_C_025c0d96-8ec2-4708-aef7-42782b81″ />Toiletries.
Ah toiletries. You ninny-woods always seem to take up more space than you have any right too. Here’s a secret- you don’t need full sized bottles of everything under the sun.
Travel sizes exist for a reason. Solid cologne, shampoo bars, packing clothes that don’t need ironed. There’s a bunch of ways to minimise the unnecessary bulk your toiletry bag usually requires.
Gone are the days of me packing “just in case” deodorants and toothpaste. If I’m not using it daily back home, I will not miss it on holiday. And chances are, if you accidentally run out of whatever, your resort will have plenty on site.
But if not, any local pharmacy will have travel sizes should you find yourself in a pinch. <img class=”size-full” src=”http: //joewears.co.uk/wp-content/uploads/2025/04/im1979_Packing_for_Portugal_building-a_vacation_wardrobe_-dd3f1c33-82c0-40b3-8b46-1abb91f8b901_1.jpg” alt=”im1979_Packing_for_Portugal_building-a_vacation_wardrobe_ -dd3f1c33-82c0-40b3-8b46-1abb91f8b901_1″ />Speaking of packing, let’s talk about how I actually fold vs. roll everything. I like to roll all thin clothes (tank tops, t-shirts, underwear, socks, swimsuits) as tight as humanly possible.
Button ups and trousers I fold in half using the natural creases of the clothes and lay them flat.
Heavy jackets and coats (yes I will occasionally pack a coat) get turned inside out, folded in half, and stuffed on top. All of this fits into the comfortable backpack sized bag above. And yes I could’ve saved another article of clothing by wearing that white t-shirt on the plane but I was already wearing that hoodie.
I also always travel with an extra pair of trainers since those bad boys can handle a week’s worth of abuse and rinse and reload in the sink. Phew! Alright guys that’s all she wrote.
I know that’s a ton of information to digest so if there’s anything you’d like me to expound on, shoot me an email or comment below. As always, safe travels and pack responsibly! Oh wait, one last thing… outerwear. coats, jackets, hoodie, call them what you will.
If you’re tight on space, wear your bulkiest layer on the plane. Trust me, you’ll be thankful for that extra layer when your feet decide your plane seats freeze at night and those extra ounces save you from checking a bag.<
