Two weeks ago, I flew to Montreal for a 5-day visit to see my best friend, who moved there in 2021. It was almost exactly 3 years since the last time I was on a plane back in March 2020, though that feels like a lifetime ago. I was thrilled to be seeing my bestie – the last time I saw her was a year ago when she came back to Edmonton for a visit – and excited to be in Montreal again, but I also felt plenty of anxiety. I was never a frequent flyer even in pre-pandemic times, but it’s safe to say that I’ve lost my “muscle memory” for plane travel in the intervening three years. Thinking about going to and through the airport, getting on a plane, and repeating the process all over again made me feel a little nauseous.
To make my life easier, I decided to do something I’d never done before: take only a carry-on. This might seem like no big deal for some of you, but I have never travelled by plane without checked luggage. If it takes a plane to get there, I need a suitcase of clothes to come along with me. While I’ve gotten better over the years about not over-packing, I still need the security blanket of extra clothing options, “just in case”. Well, not this time. This time, I had to prepare a bare-bones packing list – a new challenge for me, especially considering how out of practice I’d gotten.
I started by breaking down my needs. I had 2 travel days and 3 city days to cover. To help pack light, I decided I would wear the same outfit on the plane both ways, and that I would only bring one pair of shoes to wear the entire time. Because I knew I would be doing a lot of walking (and it would still be fairly cold), the shoes would be a pair of flat-heeled, black boots that could be worn with both pants and skirts/dresses. That left me with at least 3 outfits to figure out.
While my bestie and I didn’t have plans to do anything super fancy during my visit, I was still going to be in Montreal; I wanted to look nice, but also needed my outfits to be comfortable since I would be wearing them all day to a variety of activities (mostly museum hopping, dining out, and shopping).
I started with the bottoms. One was going to be a pair of jeans; easy to dress up and down, comfortable enough for the plane, hard-wearing. The choice of jeans was a no-brainer: my kick flare Tommy Hilfiger pair. The pant leg is wide enough to accommodate the (knee high) boots I planned to wear, and the cropped length meant that I wouldn’t have to worry about getting them wet if there was snow on the ground.
Technically, I probably could have brought only the jeans and a bunch of tops, but I wanted some variety so I decided to bring a second option: a skirt. Picking which skirt to bring seemed daunting at first – I have a lot of skirts! – but in the end it was actually pretty easy. I knew I wanted a long skirt and something that wasn’t too “precious” (i.e. I could wear on snowy/muddy streets without worrying about it). I ended up choosing my Cleo plaid wrap skirt. It’s black but has a nice pattern – not too loud, not too subtle – to make it more interesting. It’s a lightweight wool blend material, which is easy to wash; plus, I paid $5 for it, so even in the worst-case scenario — total destruction — it’s not a huge loss.
By the time I got to tops, my decisions were already much easier, since the bottoms I had selected helped to narrow down my options. Well, the skirt did, anyway. I picked tops based on what would work with the skirt, since I knew they would always work with the jeans too. I ended up choosing 2 sweaters, 1 cardigan, and a button-down shirt. This might seem like a lot, but I had to consider layering options – I would be outside a fair bit, and my winter coat isn’t super heavy. For that reason, I also added a thin (cotton) turtleneck; this functions as a base layer in the winter and I don’t count it as “real clothes”.
Lastly, I added the “functional” items: a sweatshirt (for the plane, and for lounging at my friend’s house), a pair of leggings and a long sleeve t-shirt (also for lounging), plus of course PJs, socks and underwear, hat, scarf and mitts.
With this packing list, I was able to create 6 easy outfits (double what was strictly necessary, as insurance):
I ended up wearing 4 of these outfits and was pretty happy with them all: