On Friday, my husband, Frank, and I will be heading off to Toronto for the weekend to celebrate Frank’s birthday on the 25th.  He turned 50 the first year of the pandemic which was just about the suckiest way to celebrate half a century.  Frank also has an obsession with Canada.  I don’t know why.  This passion has been around long before people started discussing cheap Canadian prescription prices, how Canadians supposedly don’t lock their doors, or how their Olympic uniforms always manage to outshine ours no matter how hard we try.  Frank is a fervent hockey fan, which must play into his obsession to some degree, and the rest, I just shrug off as one of the odd things that make my Mazzy —my nickname for him because his last name is Mazzola —who he is.   When we made the plan to go to Toronto for his birthday, it was before Frank wound up in the hospital a third time for the same heart issue he’s been having (nothing too serious, thankfully), so it makes this trip feel even more special and timely.

Despite it being just a long weekend and a quick hour and a half flight from New York, we had a lot of things to get in order.  Both our passports expired during the pandemic lockdown, we had to reassess some of our travel gear, and, of course, I had to figure out what I would be wearing.  In a conversation about what we would be packing, Frank commented that he was thinking about this too and I said, “No, Mazzy, I need Toronto looks.”  As if Toronto has “looks.”  Basically, what I meant was I was kicking around in my head what was going to get packed that could be mixed and matched for the plans we had.  I thought I would share this capsule with you and what I envisioned I would be wearing with the understanding that once I get there would be some flexibility that things could change.  

My Toronto Weekend Get Away Capsule

toronto weekend

This is an overview of what is going into my suitcase.  My plan is to pack things that travel well, won’t easily wrinkle, are easy to mix, and can be worn multiple ways.  I selected two pairs of comfortable walking sandals, something packable to wear to Frank’s birthday dinner, things to wear for walking and sightseeing, and pieces that could be worn for a nice, casual dinner.

Being a New Yorker, it’s rare that I get to be a tourist in a big city, so when I get the chance to go be one I love it.  When I was in Seattle a few years ago, I dove in head first and did all the touristy things just like people who visit New York do.  I lean in, because, why not?  This is my first time in Toronto and Frank’s second (his last time was many years ago), so on this trip, we’ll probably get the more common things out of the way.  Given Frank’s love of Canada, I’m sure this won’t be our only trip to Toronto, so if we don’t get to everything or don’t make it to places more off the beaten path, I’m sure we’ll get to them at some point.

My looks

To give you a better idea of how I will be utilizing the pieces in my capsule, this is how I envision wearing what I am packing.  


toronto weekend

Is it old-fashioned that I like to dress a bit to fly?  I know I am an outlier as I see what people wear to the airport.  I’m not flying to the moon, the flight to Toronto is shorter in time than it takes for me to get to my sister’s house in New Jersey.  This is my typical flying look. I always wear slip-on shoes to make it easier at the TSA checkpoint but never open-toe. I pack a large scarf, and always wear my glasses because the air gets dry on planes.  

My blazer is a lightweight style I’ve had for years that travels well.  I plan on wearing a grey vintage v-neck tee, straight-leg jeans, and cognac belt, from J.Crew, and my M.Gemi driving loafers.  The Etsy scarf I bought from this seller is so lightweight and soft, light and drapey.  My carry-on is a Longchamp nylon crossbody I got resale from The RealReal that will also be my sightseeing bag.

Where We’re staying

We decided to stay at the Omni King George because it’s not only a gorgeous hotel but it seemed to be in a great area and local to most things.  This trip is more of a celebration weekend and less of a, “let’s just find a place to sleep,” so we decided to stay at a hotel that was beautiful and had history.  The Omni King Edward Hotel is Toronto’s First Luxury Hotel, built in 1903 and was granted its name by namesake King Edward the VIII.  Being someone who never passes up a good cup of earl grey, I am going to try to make one of their tea services at 4 pm. 

Omni King George Toronto

Friday Sightseeing

Toronto Weekend

We have a very early flight on Friday to give us enough time that day to get some sightseeing in.  Once we arrive, get some food in us and can change, we’ll be out and about and plan on doing some local walking.  I can do a quick change and swap out my blazer for a cardigan if I need it.  If not, my Longchamp bag is large enough to just throw it in there. I’ll change my shoes to my Birkenstocks, which are always great for a good deal of walking.  My cardigan is an old Uniqlo linen/rayon style, my Birkenstock Gizehs are in their alloy patent, exclusive to their website, and the rest of the look is the same.

What We Plan to See

Right near our hotel, there are a few well-known places we want to check out.  One is the St. Lawrence Market, which is a city landmark and one of the oldest markets in Canada with roots that date back to 1803.  Over 200 vendors sell all types of foods.  We will head to The Distillery District which is a quaint pedestrian-only area that once housed a large whiskey distillery. Now,  its cobblestone streets are lined with hip indie restaurants, bars, and boutiques. Lastly, right nearby, the Canadian show we watched on Netflix called Kim’s Convenience about a Korean-Canadian family who ran a convenience store.  The convenience store used as the storefront on the show is right near our hotel and that store kept the show’s signage  How can we not check it out?

Old Toronto

Friday Night Dinner

Toronto Weekend

I am positive a shower will be on the agenda before I change into a fresh pair of clothes and we head to dinner, possibly with Canadian friends we have tentative plans with.  Whether with our friends or not, Frank and I have a casual dinner planned, so I’ll just be wearing a nice summer look with my Saint Jame Breton, white flare crop jeans from J.Crew, I’ll bring my navy cardigan if it gets cool in the evening, my grey Birkenstocks, a pair of link hoop earrings and an old teal crossbody from Ines de la Fressange for Uniqlo I got years ago and still love.

Where We’re Heading for Dinner

Choosing a place to eat Friday night in Toronto was impossibly hard.  I live in a city of tremendous cuisine and I’d say Toronto goes toe-to-toe.  How do you decide?  We wanted to stay close to the hotel assuming we’d be a bit tired and when I found Marked, a restaurant that features the culture, flavors, and spirit of South America and emphasizes natural wood-burning cooking, I fell in love with the menu.  Frank never turns down a menu with octopus, so I knew I had him sold.  They have patio seating, a casual atmosphere, and handcrafted cocktails.  It seemed perfect.

Marked Toronto

Sightseeing Saturday

Toronto Sightseeing

This will be our only full day in Toronto.  We don’t want to feel like we’re not getting in some relaxation but we also don’t want to feel like we’re not taking advantage of our time there.  I keep trying to pack things in and Frank keeps looking at me like I’m crazy, which is not unusual, by the way.  One thing we did agree on is that we’re splitting up our morning on Saturday.  After a leisurely morning, he is going to the Hockey Hall of Fame and I’m not.  I could but I want him to enjoy it.  So I’m toddling off to the BATA Shoe Museum.  We’ll meet up for lunch afterward, and, of course, go to the CN Tower.   We haven’t nailed down what we’ll do after that.  Maybe we’ll get on one of those sightseeing busses, or a harbor tour, or maybe we’ll get lost and discover the city, or maybe I’ll do some more research.  I’m open to suggestions. 

What I’ll Be Wearing

For a day of sightseeing, I am packing these ridiculous but comfortable pants I buy on Amazon.  I’m not kidding.  I bought a dusty coral pair a few years ago for nothing dollars and now I have a second pair.  They’re so comfortable and surprisingly well made and flattering.  I’ll throw on a tee, grab my cardigan if I need it, and wear my Eileen Fisher sneaker sandals that are heavenly for walking.  I try to avoid wearing the same shoes two days in a row when walking a lot.  It tends to be better for my feet.  My Longchamp crossbody will be my bag of choice again.

toronto weekend

Frank’s Birthday Dinner

sotto sotto

This was all Frank’s decision after getting recommendations and doing research.  We’re heading to Sotto Sotto which is an Italian restaurant opened in 1993 by Marisa Rocca who had only recently emigrated from Rome to Canada when the restaurant business was very male-dominated.  Sotto Sotto went on to become a huge success with a loyal following, even among a few celebrities.  They serve south-central Italian fare in a cozy environment and only use the freshest ingredients.  I’m not ashamed to admit it, I’d be willing to fly an hour and a half just to try Sotto Sotto’s food.  

What I’ll be wearing

The t-shirt dress I got from Monrow resale will be a perfect choice because it will pack well but wears much dressier.  I’ll throw on my Lizza Nuova platform sandals from M.Gemi, which are super comfortable for walking despite the fact that we could, but probably won’t, walk there.  I’ll grab my large travel scarf, teal crossbody, link necklace, and these drop earrings, and I’ll be dressed well for dinner in a travel-friendly look that is comfortable even after I can guarantee I’m incredibly full.

toronto weekend

Sunday’s Last Day Look and Flying Home

Toronto weekend

We have a later afternoon flight so we could get some extra time in Toronto but after reading there has been a lot of chaos at Toronto’s Pearson airport with major delays and flight problems, we’re not sure how early we’ll need to leave.  But we’ll still have some time. I’ll wear what I’m planning to wear to fly home as our day won’t involve that much walking or sightseeing.  

Unless something got stained along the way, I’ll wear my white jeans, Breton, and navy blazer and finish the look with my cognac driving loafers and belt.  I’ll have my Longchamp crossbody with me and the hotel can store our luggage.  If it is super hot, I’ll keep my blazer in my suitcase until we depart.  

A Few Things to Note:

  • I will be bringing more than one grey and navy t-shirt.  See the reason above.  I want to be prepared for stains.  A Tide stick also always goes in my suitcase.  
  • My capsule is flexible. I may not wear these exact outfits and the benefit of capsuling this way is that any look can be modified very easily.  Sometimes you don’t know what you want, feel, or need to wear until you’re in the moment, but a capsule can still provide a framework.

Some Travel Essentials


Eagle Creek Packing Folders
Pop Sonic Toothbrush

TravelPro Luggage & Accessories

Eagle Creek Packing Folders & Cord Travel Case

Pop Sonic Toothbrush & Silicone Travel Jars

We bought Frank’s new carry-on at TravelPro, my new favorite destination for travel luggage, recommended to me by my assistant, Rachel, who did a short stint as a flight attendant after college.  TravelPro was started by a former pilot who invented the Rollaboard suitcase (you can thank him for why your suitcase has wheels) and is the most trusted luggage company by flight crews.  Frank bought the Maxlite® Air Carry-On Expandable Hardside SpinnerWe also bought new passport covers and luggage tags.

Years ago, a client of mine showed me her Eagle Creek Packing Folders.  These folders come with folding boards you use to fold your clothing items in neat stacks which you then secure in the velcro sleeves which compress your garments to keep them from wrinkling and jostling around and so you can fit more in your suitcase.  I also picked up this cord organizer for travel because with every piece of technology I buy a new cord has to get involved.

I used to use all the free contact lens cases I’d get in my boxes of saline solution to store creams and lotions for quick trips but I recently upgraded to these cute little silicone jars. Lastly, I love these cute Go Sonic Toothbrushes by Pop Sonic.

Another thing I never travel without, Scotch Tape.  You never know when you might need to put an extra seal on a bottle of something.  I carry most things in reusable Ziploc bags.

Canada, Here I Come

I’m really looking forward to this trip and getting away.  I’ve never been to Canada before and while I may not have the same level of enthusiasm for the country that Frank does, simply because nobody does, I do love Canada.  My Canadian clients are some of my favorite people, and don’t believe the hype about Canadians being these freakish pushovers.  My Canadian clients are some of the sassiest ladies I know.  Plus, after too long rambling around New York, it will be nice to explore somewhere new for a few days.  Oh, Canada, here I come.