My Best 5 Rules To Level Up Your Travel Style: Carry-On Only

For reference, here’s what I brought: three bottoms (a skirt, trousers, and denim), two sweaters (one heavier, one medium weight), one blazer, four fitted tops (a crew neck, deep V, turtleneck – all black – plus a chambray button-up), one ball cap, one fanny pack, one purse, one belt, one coat, a scarf, sneakers that doubled as running shoes, and waterproof walking boots. Plus a small running kit. That’s it. Two weeks, three countries.

My Best 5 Rules To Level Up Your Travel Style: Carry-On Only

Rule 1: Use Packing Methods as a Loose Guide

You’ve probably heard of methods like the 5-4-3-2-1 (five tops, four bottoms, three dresses, two shoes, one jacket – or some variation). I tried it, but I kept having trouble filling the categories. Five of anything felt like too much for some things and not enough for others. It just wasn’t intuitive for me.

What worked better was starting with the 3-3-3 method: how many outfits can you make from three pants, three tops, and three shoes? That clicked for me. I used it as a jumping-off point, adjusted as I went, and ended up with something like 4-3-2-1: four shirts, three bottoms, two sweaters, one blazer.

The takeaway? If you like capsule challenges, use these methods as loose inspiration – not rigid rules. Find what feels intuitive for YOUR brain and adjust accordingly.

Rule 2: Make Your Outerwear Work Hard

If you’re traveling somewhere cold, your coat is probably the biggest part of your outfit every single day. So make it count. Bring one that has personality – a different color, an interesting texture, something that feels styled rather than just functional.

I brought a dark green peacoat, slightly oversized, and partway through the trip I bought a butter yellow toque (beanie, for the non-Canadians). I wore that hat constantly. Because my coat was such a dominant visual element every day, having pieces with personality made me feel put-together even when I was technically wearing the same thing over and over.

Traveling in warmer weather? Apply this to your bag, your sunglasses, or a fun sun hat. These are small, easy to pack, and give every outfit a boost. Don’t underestimate the power of one or two bold accessories you’ll wear daily – you won’t get tired of them, I promise.

Rule 3: Vary the Fit of Your Tops

This was huge for outfit versatility. Among my tops, I made sure I had two or three varying degrees of fit – some super fitted to the body, some with a bit more room.

Why? Layering. Because I had really fitted pieces, I could wear them under my chambray shirt AND under both sweaters. I could also layer the chambray under the sweaters. Having tops of different fits gave me so much more playing room to create completely different-looking outfits from the same pieces.

If everything you pack is the same level of fitted or the same level of oversized, you’re limiting your layering options. Mix it up.

Rule 4: Pack Tops That Dress UP, Not Just Down

This was a big revelation. Having a top that can be dressed up is way more useful than having one that can only be dressed down.

I brought a super deep V bodysuit thinking it would be great for going out and feeling a little sexy. And it was! But I couldn’t really wear it during the day – there just weren’t many occasions for it on this particular trip. It worked fine as a layering piece for warmth, but I had enough other tops that served that purpose.

What I realized: a more basic, elevated top – like my simple black crew neck – would have been more valuable overall because it could dress up OR down. Unless you have a specific fancy event with a dress code, lean toward versatile classics that can go either direction. Save the statement pieces for trips where you know you’ll need them.

Rule 5: Figure Out Your “Non-Neutral Neutral”

This will look different for everyone depending on your closet and aesthetic. A non-neutral neutral is something that’s not technically a neutral color, but functions like one in YOUR wardrobe – it goes with everything you own and adds just enough interest to keep things from feeling too basic.

For me, that’s olive green, denim (especially lighter washes), and stripes. On this trip, my denim and a striped piece were the non-neutrals that added personality without complicating anything. They might not seem “interesting” to someone else, but for my minimal aesthetic, they provided exactly the right amount of visual interest.

Bonus tip: I also brought a leather mini skirt with a dramatic hemline. I’d never traveled with something so singular before – you’d think a leather mini is only for going out, right? But in Milan especially, I wore it constantly during the day with tights and chunky boots. If a leather mini feels too drastic for you, try a standout accessory instead – something with texture or interesting details that makes simple pieces shine.

One More Thing: Stick Format Everything

I got stopped in Denmark and had to surrender some of my beloved hair products. Heartbreaking. But you know what saved me? My shampoo bar and all my stick-format makeup. When you’re traveling carry-on only, having skincare, makeup, and hair products in solid or stick format is a game-changer. Build a little travel kit of these and you’ll breeze through security without sacrificing quality.

Go Forth and Pack Light

That’s everything I learned from two weeks of carry-on travel across three countries. The biggest takeaway? Be intentional. Every piece should work hard, layer well, and make you feel like yourself. When you nail that balance, you’ll never feel like you have nothing to wear – even out of a tiny suitcase.

Happy travels!