Dress for success – Can I still wear a dress?

Dressing for success seems to be a very different problem for women than for men. Not to say that men can’t or don’t have similar pressures when it comes to outside professional appearance. It does however seem to be a theme that what a woman is wearing can often overshadow great work she’s doing.

One of my favourite anecdotes on this topic is Karl Stefanovic, the Australian TV presenter who wore the exact same suit for 12 months straight. He wore the same thing to point out the sexism that his female colleagues experienced based on what they were wearing. Karl got to the stage where he had to announce that he had been wearing the same suit for a year straight because NO ONE NOTICED. At the time he was on television every morning Monday to Friday plus various other TV appearances. 

This is not a unique example either. We’ve seen this repeated in Hollywood where female actresses are asked questions exclusively about their outfits at premieres, while their male colleagues are asked things about the movie they were in – you know, questions about their actual job. 

Tayla Harris who in my opinion is one of the best female AFL players of all time, received a flood of abuse and threats when a photo of her kicking a monster goal was posted on Instagram. A moment that should have been triumphant and celebratory was tarnished by trolls trying to tear her down based on what she was wearing. Remembering that not only was she wearing a uniform, but she was also technically at work!

Below see a picture from the @afl Instagram page of Jeremy Cameron performing a similar kick. You’ll notice that his post did not attract the trolls or comments about the length of his footy shorts.

The Duchess of Cambridge who is in fact going to be an actual queen one day, consistently appears in the news being labelled an ‘Outfit Repeater’ – as if the idea of wearing a $5,000 dress more than once is outrageous. When I Google her, the top results are all about her best fashion looks, instead of her copious amounts of charity work with a variety of causes – most particularly the mental health of children.

Should it matter what we wear?

I wanted to write this blog post because I think that a lot of women feel uncomfortable about their clothing choices and how this can impact their career. Unfortunately, it’s a fact that women can often be judged on their appearance. Clothing aside, I know that I have a very young looking face, and people often make snap judgements about me based on my age. I went through a phase of wearing a tonne of make-up to try and hide that fact. Probably ended up making me look younger anyway.

So what does this mean for us? Do we need to try and dress “older”? Dress more seriously or more “masculine”? Should we care about how we look at all? 

I like looking pretty. There, I said it. Does that make me a bad feminist? I don’t think it should. At the same time, I don’t think that judgement of my work performance should be impacted by how I dress either. So here are some Dos and Don’ts that let you straddle the line between being yourself, and being professional.

DO wear stuff that makes you feel confident

I’m going to confess now that I feel like I have very bad fashion skills. Is fashion a skill? Doesn’t matter what it’s called, I’m not the best at it. So I spend a lot of my time in dresses because I find it hard to go wrong with them. There’s also something about a pair of black slacks with a nice top that is simple and professional at the same time. 

The reason I mention confidence as a point when dressing for success, is that what you wear can inform how you feel about yourself. I know on days where I’m wearing a classic professional outfit with a killer pair of heels, I feel like I can walk into a room and dominate it. When I’m working from home wearing a pair of trackies with no make-up, I don’t feel as kick-ass. I think it’s the same theory as making your bed every morning – if you start off feeling accomplished and fierce, then your attitude for the rest of the day will be like that. 

If red lipstick makes you feel confident, and it’s appropriate for your workplace – wear it! There’s no need to mute your personality and there’s nothing wrong with expressing it with what you wear. 

Tessa dressing for success-a

I’ll also make a comment that this isn’t the same for everyone! Some people don’t feel their confidence is impacted by the way they look. I just feel like when I’m getting ready I’m putting on my battle armour and war paint.

DO dress professionally for your context

Make sure that the outfits that you choose are professional and make sense in your workplace. If I turned up in a full corporate suit to work, my colleagues would probably ask me if I had a job interview somewhere else. Being in the tech world, workplace wear is becoming much more business casual. 

Another cliche I’ll mention here is ‘Dress for the job you want, not the job you have’. I do believe putting in the extra effort subconsciously shows to everyone that you take yourself and your job seriously. It’s not the only thing that’s going to get you a promotion, but it is going to get you ahead more than wearing a Snuggie to work will. 

DON’T be afraid to appear feminine

This is a tricky one, because I think ‘feminine’ is going to mean different things to different women. There’s nothing wrong with wearing only black power suits if that’s what you love wearing. But don’t try and imitate your male colleagues to try and fit in the boys club. You’re a woman, and there’s no reason to hide that. If there’s people at your work that won’t take you seriously because you’re wearing a dress, then they probably have problems with women in general – dressing like them is not going to help you. Hiding who you are will never help you. 

Something I’ve always stood by is that people will form opinions about you when you walk into a room – it’s up to you to change them. Someone might look at me and think that I’m a “sweet young thing” that doesn’t know much – but I’m great at my job and when they walk out of the room they will forget what I looked like and remember what I said. 

I’m not going to lie, this point makes me scared that people are going to call me out for being sexist or transphobic. What I’m really trying to get at here is that you shouldn’t be ashamed of what you are. Dress whatever way makes you feel your best and no-one should judge you for that – no matter what it is. 

DON’T worry about people’s opinions 

At the end of the day, I go back to my original statement that what you wear shouldn’t matter at work. If people are going to judge you by what you wear, then ultimately it doesn’t matter what you wear – because they’re not seeing the real you. Let your work speak for itself and what you stand for. And don’t be afraid to wear that dress – more than once.

4 thoughts on “Dress for success – Can I still wear a dress?

  1. I love this article. As we are all working from home I think getting dressed to project what we are doing that day does add to our confidence and motivation that we are still working and achieving as we were. Having a walk/Run/class then shower and change into our maybe less formal work wear gets us ready for the day!


    1. Absolutely! I’ve found that during COVID, what I wear matters much more as you don’t have the normal prompt of heading into the office. It’s tempting to hide behind turning off your camera and staying in your PJs. I’m so much more productive on the days where I treat my home office like the real office.


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