I Finally Cracked the Code: One Carry-On for Every British Weekend Away (After Years of Luggage Disasters)

Okay, so I need to come clean about something embarrassing. Until about a year ago, I was that person who packed like I was moving to a new country every time I went away for a long weekend. I’m talking three different coats for a two-day trip to Brighton, five pairs of shoes for a weekend in Bath, and enough “just in case” outfits to stock a small boutique. My poor boyfriend Jake has literally watched me sit on suitcases trying to zip them shut while insisting I’d “really pared it down this time.”

The wake-up call came last May bank holiday when we went to the Lake District for four days. I packed like we were going on a month-long expedition to multiple climate zones. We’re talking hiking boots, three different rain jackets (because what if one wasn’t waterproof enough?), dressy clothes for hypothetical fancy dinners, casual clothes, athletic clothes, and basically my entire summer wardrobe because the weather forecast kept changing.

When we got to our cottage – which was gorgeous but had about as much storage space as my Portland studio apartment, meaning basically none – my massive suitcase became this hulking presence in the middle of the bedroom. Jake tripped over it trying to get to the bathroom at 2am and let out a string of words I’d never heard him use before. The next morning, watching him drag my suitcase across uneven cobblestones while I carried my “light” day bag stuffed with backup outfits, I realized I had a problem.

That’s when I decided enough was enough. I set myself a challenge that honestly seemed impossible at the time: create a bank holiday wardrobe that fits in a carry-on, works for literally any UK destination, and doesn’t leave me wearing the same three outfits on repeat. After testing this system on trips to Edinburgh, Cornwall, and a very rainy weekend in York, I think I’ve actually figured it out.

The secret isn’t just about bringing fewer things – though obviously that’s part of it. It’s about being really strategic with what you choose so every single piece works overtime. Like, graphic design principles but applied to packing. Every item has to serve multiple functions and work with everything else you’ve brought.

Let me start with bottoms, because honestly this is where most people go wrong. The foundation of my entire system is finding one perfect pair of jeans. Not just any jeans – I mean the holy grail pair that’s comfortable enough to wear on a three-hour train ride, looks good enough for dinner somewhere decent, and doesn’t lose its shape after multiple wears. For me, that’s a pair of vintage Levi’s 501s I found at a thrift store in SE Portland. They’re this perfect faded blue that goes with everything and they’ve gotten better with age instead of falling apart like most of my budget finds.

Along with the jeans, I bring one versatile skirt or dress. My go-to is this black midi skirt from COS that I got on sale for like £30. It has an elastic waist – comfort is not negotiable when you’re traveling – and it’s made from this amazing fabric that literally never wrinkles. I can stuff it in the bottom of my bag and it still looks presentable. During the day I wear it with a t-shirt and trainers, but at night it works with a nicer top and different accessories.

If it’s going to be cooler or if I’m planning any slightly fancier dinners, I also pack one pair of black trousers. Nothing too formal, but something with a bit more structure than leggings. Mine are from Arket and they have this relaxed wide-leg cut that’s comfortable but still looks intentional. They’re perfect for country pubs or if you end up somewhere that feels too nice for jeans.

The tops are where the real magic happens in terms of versatility. I stick to exactly four: a white t-shirt that doesn’t go see-through when it gets wet (learned that lesson the hard way in Edinburgh), a Breton stripe because I’m apparently incapable of traveling in the UK without looking like a walking cliché, one lightweight knit for layering, and one “going out” top. The last one is usually this silk camisole I found at a vintage shop that takes up basically no space but immediately makes any outfit look more evening-appropriate.

Outerwear is where I used to completely lose control – bringing multiple jackets for every possible weather scenario. Now I limit myself to two pieces: a packable rain jacket from Uniqlo that folds into its own little pouch, and a navy blazer that doubles as both a smart layer and extra warmth when needed. The blazer is probably my best investment piece – I got it at Zara three years ago and it still looks great despite being worn constantly.

Shoes. Oh god, shoes. This used to be where my packing completely fell apart. I’d bring hiking boots and heels and sandals and backup trainers… it was ridiculous. Now I’m strict about three pairs maximum: white trainers that work with literally everything (mine are Superga knockoffs from Target that have held up surprisingly well), comfortable walking sandals for when the weather’s decent, and one pair of smart flats that fold completely flat in my bag. The flats are these leather ballet shoes from M&S that cost about £20 and have survived multiple trips without falling apart.

For accessories, I keep it simple: one crossbody bag for daytime that fits my camera and wallet without destroying my shoulders, a small pouch that can work as an evening bag, minimal jewelry that goes with everything, and one light scarf. The scarf is key – it works as sun protection, extra warmth, a beach cover-up, or even a makeshift pillow on uncomfortable train journeys.

The last essentials are swimwear and sleepwear. One bathing suit (let’s be realistic about how often you’re actually swimming in Britain), pajamas that wouldn’t be mortifying in a hotel fire alarm situation, and enough underwear to handle the different cuts and styles of everything else you’ve packed.

When I pack all this using the rolling method and packing cubes – which I was skeptical about but they actually work – it fits easily in a standard carry-on with room left over for souvenirs.

But here’s where it gets really good: how these pieces actually work together for different types of trips. For a city weekend with museums and nice restaurants, I wear the black trousers with the white t-shirt and blazer during the day, then switch to the silk camisole for dinner. Trainers for walking around, smart flats for evening. The crossbody bag works for both.

For a coastal trip with beach walks and seafood dinners, it’s jeans with the Breton stripe and rain jacket for breezy cliff walks, then the skirt with the knit top for dinner watching the sunset. Sandals if it’s warm, trainers for longer walks or cooler weather.

For countryside weekends with hiking and pub meals, jeans with the white tee and knit for walking, adding the blazer for pub dinners. The rain jacket stays in the bag because… well, it’s Britain in summer, so obviously it rains at some point.

I actually tested this system properly last summer when Jake and I did this five-day trip that hit Edinburgh, the Scottish coast, and the Borders countryside. My single carry-on handled all three destinations perfectly while Jake watched in amazement, having gotten used to me traveling with enough luggage for a small family.

What I’ve learned is that successful light packing isn’t about suffering or wearing the same outfit every day – it’s about being really smart with your choices. Each piece needs to be the best possible version of what it is. Like, don’t just bring any white t-shirt, bring the perfect white t-shirt that fits well and doesn’t look cheap. Don’t bring random jeans, bring the ones that make you feel confident and work in multiple situations.

Color coordination is huge too. I stick to navy, white, black, and denim blue with maybe one accent color if I’m feeling adventurous. It sounds boring but it’s actually liberating – everything works together so you never have those moments of “I brought this but it doesn’t go with anything else.”

Of course, there are always destination-specific tweaks. A city break might need slightly smarter shoes if you’re planning fancy dinners. A beach holiday might justify a second bathing suit if you’re actually planning to swim every day. A hiking trip might require real boots instead of trainers. But the basic principles stay the same.

Weather planning is probably the trickiest part of packing for Britain because you literally never know what you’re going to get. I’ve been in situations where I needed everything from sun protection to waterproofs in the same afternoon. The layering pieces are crucial – the knit works under the rain jacket, the scarf provides extra warmth or sun protection, the blazer works as a light jacket for mild evenings.

One thing I refuse to compromise on is toiletries. After a disaster with hotel shampoo in Bath that left my hair looking like a bird’s nest, I now decant my regular products into travel containers rather than gambling on random hotel amenities. Same with skincare – travel is already hard enough on your skin without throwing unknown products into the mix.

I try to be disciplined with tech too. Phone, portable charger, and my Kindle loaded with backup books. Laptop stays home unless absolutely necessary because bank holidays should be about disconnecting, and most work emails can wait until Tuesday anyway.

The ultimate test of this system came when my friend Sarah joined us for a weekend in Whitstable. After three days of seeing me in different outfits from my tiny bag, she asked how I’d managed to pack so many clothes. When I explained that she’d seen my entire holiday wardrobe just styled differently each day, she couldn’t believe it. “But you didn’t repeat anything,” she said. Same pieces, different combinations – it actually works.

The best part isn’t just the practical stuff like not having to drag heavy bags around. It’s the mental freedom of not having to make a million decisions about what to wear or worrying about whether you brought the right things. You know you have exactly what you need and nothing more, so you can actually focus on enjoying your trip instead of managing your luggage.

So next bank holiday, when you’re staring at an empty suitcase wondering if you need three different “just in case” outfits and shoes for completely hypothetical situations, I dare you to try the carry-on challenge. Your back will thank you, your travel companions will thank you, and you might discover that having fewer options actually makes getting dressed easier, not harder. Sometimes limitations really do breed creativity – in packing and pretty much everything else.