Like A Boss

How to style workwear, inspired by our favourite TV bosses

How to style workwear

Words: Afrika Lethabo Bogatsu | Photography: Higor Bastos | Styling: Kelly Fung

Women have come a long way in the workplace over the last 50 years, but the fact still remains that gender and wage discrimination are daily struggles around the world.

We’ve got a great distance to go when it comes to real transformation and progression, but that doesn’t have to stop us saluting the many women who’ve made a name for themselves and broken the glass ceiling in their respective industries. From politics to science, film and television, women have made serious advancements, and of course, have looked amazing while doing the absolute most. 

Because these women have referenced those before them and have provided inspiration to those that came after, we’ve rounded up our favourite television boss ladies to inspire your workwear wardrobe.

 A killer coat like Annalise Keating's

How to style workwear

Running around town getting coffee or lunch for your boss or meeting with clients means you definitely need a few jackets and coats for those early morning rushes. This season’s has a few strong options, from puffer jackets, and biker-inspired leather numbers to the classic camel trench coat. Whatever your personal style or work struggle, there’s a jacket out there for you. 

Boss Lady: While we’re obsessed with Annalise Keating’s dresses, we also love her jackets and coats just as much. It’s always so interesting watching how stylish and well-put together Annaliese looks while trying to make sure her life doesn’t fall apart at the seams and teaching her students How To Get Away With Murder.

Mindy Lahiri’s statement trousers

How to style workwear

While black, grey and navy are the standard when it comes to the office uniform, we think it’s about time to break the rules by adding some unexpected colour. Nothing turns heads in the office as much as a brightly coloured pair of well-tailored pants. Usually we see the colour trend in blazers, but pants are also a great way to have fun with your work wardrobe. 

Boss Lady: Our favourite OB/GYN Dr. Mindy Lahiri’s style is quirky and bright – just like her personality. Her eclectic style (even off The Mindy Project set) and unexpected pairings remind us not to take life or work too seriously and that we can and should have fun with our work outfits.

Olivia Pope’s Lady Bag

How to style workwear

Don’t miss your bus because you’ve got too much stuff. Get your life together and carry it all in a neat carry-all that is both functional and stylish. Make sure to always pack your essentials like your day planner, sunglasses, lipstick, power bank and those useful snacks for those busy days when you skip breakfast and lunch feels like a lifetime away. 

Boss lady: While we’re pretty tired of the emotional rollercoaster that is her relationship with Fitz, we’ll never ever grow tired of Olivia Pope’s style. Her bags are always on point, slung elegantly over her arm. More often than not, that’s the main reasons we watch The Fixer. That, of course, and writer Shonda Rhimes’ famous cliffhangers. 

Blair Waldorf's block heels

How to style workwear

Long, laborious days spent in the office are already hard enough, but add the burden of uncomfortable shoes to that, and it’s one step too far. For some women, sky-high heels are empowering, even though studies have shown that prolonged wearing of heels can actually be bad for your health. Luckily, there's the block heel, which offers much greater support and comfort while still being on-trend.

Boss Lady: It came as no surprise when Blair took over Waldorf Designs from her mother and made it even more of a success, because from the first season of Gossip Girl, we knew that Blair had boss lady potential. This could be seen in the way she commanded respect and fear from her minions, dressed in the preppiest of outfits right down to her court shoes. 

A figure-hugging high-waisted pencil skirt like Claire Underwood's

How to style workwear

First introduced by french designer Christian Dior in 1954, the pencil skirt has remained a timeless piece of fashion and a popular workwear item ever since. With it straight and narrow silhouette cutting just below the knee, it accentuates your curves while helping you look effortlessly sophisticated.

Boss Lady: Modern-day Lady Macbeth Claire Underwood is known for her sharp tailored suits that manage to be sexy and sophisticated but still conservative enough for a First Lady’s wardrobe. Build your own House of Cards like Claire and rock a figure-hugging high-waisted pencil skirt. We promise no one will underestimate you or your style.

Joan Holloway's knits

How to style workwear

Far from your ouma’s knits, this season’s pieces are on-trend and modern but still provide much-needed warmth and comfort for days when you're losing the office aircon war.  With sexy and sophisticated details like ruffles, frills and cut-outs, these knits will earn you some style points in the office. 

Boss lady: It’s been two years since Mad Men came to an end, but Joan Holloway still remains our favourite redhead femme fatale. She’s bold, to-the-point and takes absolutely no nonsense from anyone. Whether she was blowing smoke or laughing in people's faces, she looked incredible in everything she wore.

Cookie's statement blouse

How to style workwear

The classic white shirt is a timeless wardrobe staple, but the working woman relies on it more than most. A luxurious statement blouse with frills and ruffles in a soft silk or satin finish is a great way to add extra femininity to what could be considered a masculine suit. 

Boss Lady: Lyon family matriarch and co-founder of Empire records, Empire's Cookie (played by Taraji P Henson) is fiercely loyal, resourceful and she's also a lover of the finer things. Her over-the-top, luxurious wardrobe features its fair share of fur coats, leather pants, and our favourite silk blouses. We love how she adorns her silk shirts with lots of jewellery. 

seen this?
winter wardrobe upgrades
Home yoga starter kit
transitional dresses
latest sneaker drops