I arrived in Ottawa on a Saturday and it was -20C with the windchill. When I left on Tuesday it was 7C and raining. No, this wasn’t atypical for Canadian travel. It was March. During those shoulder season months (travel-industry jargon for March-June and September-November) it’s really hard to know what to pack.The weather can be a traveller’s greatest enemy. The big question is how to pack a carry-on for multi-season trips? What if it’s freezing? What if it’s hot enough to go swimming?

How do I fit all the clothing I need for two seasons in one carry-on? Like this.

How to pack a carry-on for multi-season trips

Layers, layers, layers

Having layers for shoulder season travel is essential. It’s important that the pieces you pack can do double duty. Light t-shirts for warmer weather make great undershirts for hiking during a snowstorm. When travelling in colder climates, a warm waterproof jacket is a necessity. I have a Columbia Mighty Lite Hooded Jacket that is super warm, and packs up very small. Perfect for carry-on travel in the late Fall or early Spring.

A match made in suitcase heaven

Everything in your suitcase needs to match. I’m serious. The flatlay below doesn’t look matchy because I wanted it to look nice on camera, it’s because it’s practical. While it may feel boring to have everything match, it’s easy to make outfits! Every top can go with every pant and vice versa.

One statement piece

Along with the matchy-matchy majority, having one or two standout pieces will help spice up the suitcase. I like to bring a sparkly top, dress, or something in a bright colour I can wear several ways throughout my trip. Keep in mind it’s important to consider how many times you’ll wear this statement piece. If you can only think about one occasion to wear it, leave it at home.

Outfit by number

One of the biggest not-so-secret-secrets about packing for a carry-on is very rational. Pack outfits appropriate for your activities. I wasn’t planning on doing any hiking while in the Ottawa area, so I didn’t have to bring any snow clothing. But I did plan on a couple nights out, so dressier tops and shoes were a necessity. This may seem like a no-brainer, but actually planning what you’re gonna wear before you go can help a lot when you’re on the road.

Here are some examples from my suitcase to show you how to pack carry-on for multi-season trips.

Visiting the National Gallery of Canada

Art galleries tend to be a little drafty in the winter months and inexplicably warm during the summer, so layers are key here. I wore my Ines de la Fressange x Uniqlo blue blouse underneath, a striped long-sleeved-shirt from Uniqlo (12) Rag & Bone jeans (4), and my Bass blue suede Oxfords (6).

Shopping in Byward Market

Shopping at this landmark market involves a lot of going in and out of stores, so I wore a breathable wool sweater from Winners (2) and black leggings (5) so I didn’t get too overheated.

Drinks & Pork Buns at Datsun

Drinks require a little flare: I wore my green bling-y jacket from H&M (1) along with my black textured leggings (5), black sleeveless top from Winners (11) and of course, a statement necklace (13).

Shivering along the Rideau Canal

Even though it closed for skating, we wandered along the Rideau Canada and it was freaking cold. I wore my Columbia Mighty Lite Hooded Jacket (3) underneath my more stylish navy dress coat for extra warmth, along with my vintage purse (8) which is the perfect size to hold both my camera and my wallet.

Late Dinner at Bar Laurel

Time to splash out with my statement jacket again (1). This time I wore it with a simple black dress and tights.

Creeping on Justin during Question Period

We took a tour of the Parliament buildings, so had to look prim and proper if we ran into JT. My Uniqlo blue blouse (9) and Rag & Bone skinnies (4) were up to the challenge.