How To Travel Stylishly & Comfortably

If you’re anything like me, you’ll know that looking stylish while on the road is often a challenge. Although I’ve done my fair share of traveling over the last few years, my trip to Montreal last month was really the first time I felt both true to my style and comfortable in what I was wearing. A part of this can certainly be attributed to my increasingly simplified personal style (hello, neutrals), but here are several more tips I’ve adopted which have helped me achieve this!

1. Versatility is Key
While packing for the trip, I tried on each outfit that I planned on wearing in its entirety. A little time-consuming, sure, but it proved to be worth it — both in the smaller amount I ended up bringing and the ease of getting dressed in Montreal. During the process, I would put together a look, then keep one or two elements of it on (like the dress) and plan another outfit around this piece. That way, I ensured that most of my clothes were worn multiple times and I wasn’t wasting space with items that I wouldn’t wear.

2. Accessorize Wisely
We’ve all heard about the power of good accessories, but during this recent trip I really came to experience it in a new way. A pair of statement sunglasses, a good red lipstick, and a couple of simple necklaces were all I brought, and so they became my go-to’s on the daily. Each piece contributed interest and helped me feel more pulled together without adding too much fuss to my looks or bulk to my suitcase.

3. Get Off on the Right Foot (and Bag)
In the past, I’d typically wear beautiful but impractical flats that would have my feet screaming by the end of the day. Then the next day, I’d compensate with runners that were comfortable but definitely left something to be desired aesthetically. I knew that our primary mode of transportation in Montreal would be our own two feet, so I packed with that in mind. I brought just two pairs – white Converse sneakers and black leather Chelsea boots (which I wore on the plane to keep my luggage light) – and alternated between them. The outfits I brought could also be paired with either, which added to their adaptability.

Another essential element to traveling well is a good choice of bag. From my wallet and a water bottle to an extra sweater and external chargers, I always find myself carrying more than usual while away — and for a longer period of time. I already wrote about one of my choices here; this backpack was a lifesaver. My other option was a black leather tote with zero hardware: perfect for when I needed a dressier option, and light enough to carry everywhere.

I hope this eases your packing woes for the next time you set off somewhere, and I’d love to hear any tips you have on staying stylish while traveling, too!

Dress: Aritzia | Vest: Club Monaco (old, similar) | Shoes: Converse | Backpack: Fjallraven (c/o) | Sunglasses: Karen Walker | Necklaces: EMMY TRINH, here and here (c/o)

Photos by Brian Chan