Why Plan Outfits for Travel? Montreal Calling

Joya Dass
5 min readAug 5, 2022

Next I head north to host a Mastermind dinner with 9 women. Montreal is one of my favorite towns to visit. It’s Europe without the jet lag. I shared a behind the scenes peak at how my Mastermind dinners work. [link]

Now let’s talk packing and wardrobe. I’ve gotten intentional about my dressing for work/pleasure trips because I used to arrive at a destination and then worry about my outfits. I don’t have regular FOMO (Fear of Missing Out) I have street-style outfit FOMO. I would get so insecure about what I was wearing that I wasn’t present, confident, or focused on the moment.

By planning ahead now, I go into events/dinners/activities with full confidence and just focus on the people and the conversation.

Montreal will be everything from formal sit down dinners to a food tour. Planning ahead allows me to cut down what I bring — and put it in a carryon!

So let’s get into it

For travel days, my go-to is always my up cycled Marine layer (a Brooklyn fave), Ralph Lauren blazer that is cut like a sweater (for some polish), jeans and my favorite kicks: Nikes. I always carry a light wool scarf from Epice for those drafty times in airports and planes.

The sky high summer heat has been blazing here, but Montreal is about 10 degrees cooler. Nights dip into the 60s, so I will have to bring a sweater or jacket

When I land its coffee and dinners with members. The city is dotted with locations that all had a former life. The Crew Collective, where I’m due for coffee, is housed in a gilded gold and marble space. It’s in a former bank turned coffee purveyor. I fully expect a teller to pop his or her head out and ask me if I’m making a deposit today. I picked a linen jacket and shorts set, paired with navy blue M. Gemi loafers. A very masculine look, but to offset it, I’ll wear a soft and feminine lacy navy blue silk cami from RL, paired with some statement earrings I found on Etsy. Dinner is at Da Emma, a former women’s prison. The tables nest between stone pylons in the subterranean space, a steady reminder of the building’s former identity.

One of my favorite ways to experience another city is to do a workout. B-Cycle is Montreal’s answer to Soulcycle, where I’m a steady devotee. My uniform is tank, tights, top, and NY Yankee proud hat.

In the evening, I host the Mastermind dinner with 9 women Thursday night in a private home and private chef. I’ll be channeling my inner muse Carolina Herrera. Tuckernuck does the job with this crepe navy blue dress featuring a high drama collar, but short enough to weather the heat.

After the dinner — — THEN I get to enjoy Montreal. My partner and some old friends fly in for dinner. Italian dining awaits us on the terrace at Beatrice. For this evening, I’m taking it down a notch with shorts and a blue transparent top. But the formality remains with the block heels from CL By Laundry and the Bottega Veneta knock off I found on Etsy (PS Etsy finds from all over the world are a GAME changer! One of a kind pieces without the expense)

Whats a stop in Montreal without a visit to my favorite water circuit spa Bota Bota, which had a former life as ferry boat. The Ruched sidestroke swimsuit from Summersalt is my go to this summer. Afterwards, I put together a walking tour of all things Montreal •

  • Beaver tail at Queues de Castor — fried dough topped with cinnamon and sugar
  • Schwartz’s Deli — Smoked meat sandwich
  • La Banquise for poutine
  • St. Viator bagel — Montrealers think their bagels are way better than NYC bagels

An AYR olive metro tank dress is sporty but elegant enough to take me from day to night. I’ll shove a white linen shirt in my straw bag, which is the biggest accessory I can carry.

Creating these outfits is something I’ve done since I was a kid.

My 4th grade teacher Mrs Taylor remarked to my mom, “I’ve never seen a kid so meticulous about matching her accessories to her outfits.”

At the time, I was very proud of a black and midnight blue sweater with a low cowl neck. I had found an interlocking wooden heart bead necklace in the exact colors, that nested perfectly in the neckline. It’s wonderful to return to the things that bring me so much joy.

I have a Mastermind, which is a premium level offering. I am currently enrolling. 👩🏻 This. is for an elite group of women leaders who have a goal & want the right group & accountability around it. Take this assessment to find out how ready you are >>www.goalsscorecard.com

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Joya Dass
Joya Dass

Written by Joya Dass

If you have a goal and want the steps to make it your reality, I have a solution. www.joyadass.com

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