One, Two, Three: Day to Night Dressing

One, Two, Three: Day to Night Dressing

I promise, there is a logical segue here. When you have more than a few things on your day’s To Do list, what you need are versatile pieces that will carry you from one task to the next.

Easy mix and match switch-hitters are a key part of putting together an eclectic style that will be as big a hit at 8 am as they will be at 8 pm, when your day is still going and night life is just winding up. Your clothes need to be chameleons that can work in multiple ways, no one needs an item that only goes with one thing taking up valuable real estate in their closet.

These looks each have at least two pieces that can easily transfer to the next outfit. Swap out #1’s black shoes for the punchy tie-up rust coloured shoes and add a polka dot clutch to wake the more subdued clothes up.

These looks were inspired by my day on Monday when I had to go 16 plus hours without going home with a triathlon of events.

#1: I was called in to do make-up for the VP of a major bank and the CEO of a non-profit, to prep them for their on-camera close-ups. They were shooting video content promoting their partnership and commitment to combating Breast Cancer, so it was important to put these clients at ease and get them ready to pitch this vital fundraising initiative. For me, in addition to being comfortable hauling and setting up equipment, it was necessary to look the part of a pulled-together make-up artist.

#2: Later that afternoon, I had lunch with my wife, walked the city and window shopped. I traded my more professional, structured top for a fun floral shell and cute shoes.

#3: I finished my play day by meeting a friend at a hip little food joint called, appropriately, The Hole in the Wall (Toronto). I traded up one final time (changing in my car) for a flippy skirt to go with (but not quite match) my floral top.

Hole in the Wall, Toronto.

Hole in the Wall, Toronto.

A hidden gem, built between two old buildings, this restaurant is long and narrow ... and full of character!

A hidden gem, built between two old buildings, this restaurant is long and narrow … and full of character!

I’ll have to say that this day of clothes hopping was entirely worth it, because after sharing some pinot grigio with my delightful friend, Katherine, and eating the best burger I can remember in a LONG time, the charming server (after overhearing our feminist conversation) dropped off a complimentary chocolate pot de creme and peanut butter dessert, layered decadently in a cute little mason jar and topped with whipped cream.

If I was going to be living it up, I certainly looked the part. Cheers to great causes, great shoes, great food and great company.


Jonathan Saunders zip top
675 CAD –

Myne plaid top
180 CAD –

Oasis shirt
20 CAD –

20 CAD –

Ezra flower print skirt
22 CAD –

Pleated mini skirt
16 CAD –

Jimmy Choo black leather shoes
1,120 CAD –

Jeffrey Campbell ankle strap shoes
195 CAD –

Klub nico shoes
140 CAD –

3 1 Phillip Lim black leather handbag
1,405 CAD –

Kayu black crossbody purse
180 CAD –

River Island bucket bags handbag
79 CAD –