5 Pieces to transition your wardrobe from recent grad to professional


The month after I handed in my final university project, I walked through the doors of my first job at a downtown Toronto design agency. I can’t remember what exactly I was wearing, but I vividly remember feeling like I ran out of outfits to wear to work that first week fast.

I knew I wasn’t going to wear a power suit and pumps, but I also knew my collection of oversized, skin-tight, or semi-sheer tops didn’t feel right.

At first black leggings felt like my secret professional weapon, but soon they made me feel like a total professional-fraud.

That wardrobe I had—the carefree whimsical eccentric unique wardrobe—stopped feeling like me. And instead started to feel like a weight holding me back from where I was going.

And when I changed my wardrobe, something more changed.

I started having creative ideas at meetings.
I started speaking up when my opinion differed.
I started owning my skills and expertise.

And I didn’t have to wear pumps and blazer to do it.

Today, I’m sharing with you, my dear friend, 5 little pieces that can make a big impact in looking (and feeling) like the professional and expert you now are, from stepping out your front door to leaving a post-work happy hour.

...Or as I like to say:
Feeling like your best self from coffee to cocktails.

Let's go!

5 Pieces to transition your wardrobe from recent grad to professional and expert




A pair of trousers

It’s not a jean, it’s not a legging: it’s a trouser. If you read my style lessons learned in 2015 post, you may have seen this one coming. Trousers changed my life. And if you haven’t yet given them a try, they might change yours too.

Does dressing professional feel synonymous with dressing up? It doesn’t have to be.

Trousers are the piece that can take you comfortably from beers with your friends, to owning your expertise in a client meeting. And it's these pieces that transition with the many facets that make up you and all the roles you take on, that help you to see yourself as the multi-dimenstional person you are.


I found my trouser-soulmate in the ankle length slim trouser. If you think that might be your jam too, I've rounded up the specific cuts I have + love:

{from 2 low end picks to 2 mid-level investments}

But there are many more trousers worth trying:

Love the airiness of maxi skirts? Try a wide leg.

Boyfriend jeans have your heart? A jogger style (relaxed leg that tapers at the ankle) is the trouser equivalent of boyfriend jeans.

Want a bit of pizazz? Try a cropped pair with a slight flare.

And once you find a shape that works for you, there’s an endless spectrum of colours, textures, and patterns you can buy them in.

Professional doesn’t mean devoid of personality.




Transitional Coat

Fur-trimmed winter coat…and then leather and denim jackets. Does that sound like your range of jackets too?

There’s nothing wrong, or unprofessional, about either of those ends of the coat spectrum, it’s just that; that it’s a spectrum and there’s an unfilled gap in the middle.

The transitional coat I’m talking about is a little longer than your above-the-hip leather jacket. It’s tailored, hood-less and fur-less. It’s sophisticated and versatile. The longer length means it pairs well with pants, skirts, and dresses.


Do you have warm but rainy springs and falls? Try a trench coat.

Are you prone to springs that still feel like winter? (I’m looking at you, Toronto...) Try a lighter weight wool blend.




A handbag that holds

A water bottle, a book, a packed lunch, a makeup bag, a camera, a laptop...a lady on-the-go can have a lot to carry.

Yet so often we buy bags for the amount of stuff we want to be carrying instead of the amount of stuff we are actually carrying.

Are you stuck in this trap? Where you’re overfilling a purse so that it is losing it’s stylish shape and the seams are coming apart? Or do you usually end up carrying a second reusable store bag to catch the overflow?

Think about what you actually carry in your work life; in your day-to-day. And ask, do you have an option that fits it all and makes you feel your most professional self?


For a classic carry-all try a tote.

Like a long strap? (I do!) I use this Fossil bag almost every day.




Pointed toe ballet flats

I told you you wouldn’t have to wear pumps and a blazer but, I cheated a little because if you didn’t know pointed toe flats are heels without the heel.

The pointed toe helps to visually lengthen the leg, flatter the ankle, and add sophistication—just like a pair of heels.


A pointed-toe take on the classic black ballet.

Or a pair in a colour close to your skin shade to further the leg-lengthening illusion:




A full-size umbrella

What does a chance of rain mean to you right now? Does it mean a tiny fold-up umbrella you throw in your purse (but will undoubtedly still get you wet if that downpour happens)? Or is it grabbing anything with a hood to protect the hair?

Let me paint you this picture:

You’re on a crowded streetcar (bus, train..) as the rain pours and wind blows, people are grabbing newspapers, throwing their hands up over their head, holding their hoods up as the wind blows them down, but you step down onto the road, press a button, up pops your umbrella, and you walk effortlessly and elegantly to your destination. When you arrive you close the umbrella and are dressed as your fabulous and professional self. No zip-up hoodie thrown on top.

Can you feel the difference?

And if it doesn’t rain and you’re stuck carrying an umbrella that doesn’t fit in your purse, it’s not such a bad thing. Hook it on your arm and feel like a chic Londoner (at least that's how I feel.)


A business-on-the-outside party-on-the-inside automatic umbrella, like this one.

Or a clear umbrella for as much light as a rainy day allows {Are you as in love with this Kate Spade one as I am?}

I don’t believe in buying “work clothes” (you know the blazer here, the dress blouse there) to feel more professional. I believe in buying clothes that move with you—the professional, expert, and put together version of you—through the multi facets of your life.

Because how you feel in a client meeting, in line at the grocery store, riding the subway, when you’re with your best girl friends—it should all feel like you. And you are always deserving of your expertise, your growth, your flourishing—in all of them.

Cheers to seeing you flourish,


PS: Want to develop a personal style that empowers you from coffee to cocktails?
My increasingly popular Find Your Style Workbook is the free gift I give to my tribe.
And it's FREE because I truly believe you deserve to trade in stress, time, money, and insecurity for confidence, clarity, and comfortability.