Getting a job on Bay Street is hard. Dressing for that job is even harder. To get some insight into how to do it well, PrecedentJD sat down with three smartly dressed lawyers and demanded they give up the goods.

Emma Williamson
Associate, Dentons Canada LLP

Emma Williamson

You need to play it safe at the beginning of your career, recognizing the impact your dress will have on how you’re perceived. Your coworkers have little else to go on but that first impression.

Choose conservative pieces: sheath dresses with jackets, shoes in pristine condition, simple jewelry and accessories. For skirts, go with knee-length or slightly above the knee. Always wear a cardigan or jacket if you’re meeting with clients or if you’re wearing a sleeveless top. To make daring fashion choices when you’re just starting out takes the focus off your talent as a lawyer during that precarious time when you’re trying to stake out space and build your identity at the firm. Once you’ve proven yourself to be bright, capable and hard-working, then you can experiment with fashion within your comfort zone (and that of your workplace).

On my first day of articling, I wore a black suit and a white collared shirt, with black pumps and a pearl necklace and earrings. Can you say cater-waiter? But it was a safe, conservative and classic outfit. I may have played it a little too safe, but that’s how I dressed as an articling student and during my first year as an associate. As I became more comfortable in the workplace and built a reputation with my colleagues, I felt okay branching out a little. I stopped wearing a suit every day, traded collared shirts for blouses and wore more colour. As the years went by, I took more fashion risks: I tried silk dresses, patterned tights and statement necklaces.

I felt confident that my colleagues knew I produced great work and that I was good with clients, so even if they didn’t like my green jacket or bright dress, at least my style wouldn’t damage my professional reputation. And now, I get to wear outfits to work that don’t make me look like a lawyer from a Getty Images stock photo!

Peter Sullivan
Associate, Cassels Brock & Blackwell LLP

Peter Sullivan

They say you never get a second chance to make a first impression, and I firmly believe this. People make snap judgments and form lasting opinions about you based on whether you look professional, healthy and confident when you meet them. It’s a subconscious thing. Lawyers will always have to demonstrate that they are worth the hours they bill, but dressing well can give you a leg up, and that’s important in such a competitive industry.

This does not mean you need to spend lots of money on your wardrobe or pay for a membership at a fancy gym. It simply means that you take care of yourself and walk into any client meeting with confidence, looking like you’re ready to do business. This means being well kempt and well rested, with your shirt ironed and your shoes shined.

Exercise, eat well, have a social activity outside of work, get enough rest and wear clothes that fit you and are in good condition. Keep your wardrobe clean and pressed. Then you will be ready to take on the world.

If you look after yourself, you’ll feel better. And feeling better will help you be better at your job.

Leila Rafi
Partner, McCarthy Tétrault LLP

Leila Rafi

Stores like Holt Renfrew and Hudson’s Bay at Toronto’s Queen Street location have personal shoppers to help you pick out great pieces — and they’re free of charge, so you can’t go wrong. I like that they push me to wear things I don’t normally wear.

Not only do personal shoppers — and even great salespeople — have a good grasp of trends, they’re also captains of the sale rack. Just recently my personal shopper saved me hundreds on an Etro jacket from the second floor at Holts. Plus, they tend to have a knack for knowing what’s appropriate to wear in a corporate setting and how far you can stretch the boundaries.

Once you have the basic pieces in your wardrobe — for women, that’s a few suit jackets and some simple pants or skirts in black, white and grey — a personal shopper can help you broaden your style horizons. They’ll ask questions about which celebrity’s style you admire, what colours you like or dislike and what body parts you like to accentuate — then they’ll determine what works best for you. They’ll show you how things you may not typically be drawn to would look nice on you. Some of the dresses I get the most compliments on were chosen by my personal shopper.

Dress code

Cracking the code to Bay Street style isn’t exactly easy. But all of our experts agreed on these finer points of dressing like a fully formed lawyer

Gentlemen

• Well-kept facial hair is fine. Just no soul patch. Ever
• When the collars or cuffs start to wear, toss the shirt
• Skip the bow tie

Ladies

• Always have a blazer hanging on your door (or cubicle wall)
• If you’re going to wear red lipstick, the rest of your makeup should be subtle
• If you’re not interested in fashion, don’t pretend to be. Stick to classic pieces

Everyone

• If you want to play it safe, don’t wear jeans in your articling year. Not even on Friday
• A little colour goes a long way. Try not to overdo it
• Always err on the side of over- dressed. That way, you’re ready for anything

To find that perfect work wardrobe, check out these three Canada-wide chains.