How Do We Dress When Working From Home?

Since quitting my agency job in November and embarking on the freelance lifestyle, I’ve been fascinated with the topic of dressing for work – at home.

Particularly for writers, there’s quite a few stereotypes and cliches floating around the internet of how we work. That we sit in weird positions whilst we hunch over our laptops (true). That a lot of our work is done at odd hours of the day when we’re feeling inspired (also true). And yes – before you say it – pants are very much optional.

But when it comes to fashion, and dressing in general – the jury is very much hung.

You see, the only real inspirations and indicators I have are the women I follow on Instagram (and Carrie Bradshaw, of course); which is why I decided to reach out to them to get to the bottom of my dilemma: is there an optimum way to dress when working from home?

Do we all really wear baggy shirts and pajama bottoms? Or is the new generation of freelancers and work-from-home-rs a little more… stylish?

I took to Instagram Stories and posed the question: Do you get “dressed up” (e.g. nice clothes, makeup, hair done) everyday when you work from home?

Out of the basic poll I received 48 answers. 44 women said no. 4 said yes.

I then asked them to expand on their answers, and I had over 50 responses come through via the comments section and DMs.

Like the general consensus on the internet, the women in my online circle were very much of mixed opinions.

Many of them opt for comfort over style, and prefer to just wear whatever is convenient and doesn’t distract them from getting their work done. Others prefer to wear lovely clothes and ‘put themselves together’ (aka, fix their hair and makeup) for a full day in their home office.

Daniella from Amity Created really resonated with me with her routine: “I don’t bother with makeup when I’m home. I let me skin breathe and only wear it if I feel it necessary when I’m out. I do make a point of getting dressed first thing though, because it helps me switch my mindset from, “I’m chilling at home in my pjs”, to “ok, I have work to do – let’s tick off this list.”

Letting my skin breathe is a BIG one. Although I’m pretty darn #blessed with my skin antics, wearing foundation etc. everyday does wreak havoc eventually. And don’t even get me started on wearing foundation and glasses. I spend half the day cleaning smudges off the lenses – but maybe that just means I’m using the wrong foundation?

Jenn from My Virtual Secretary summed up what a lot of women do quite succinctly: “It depends on the day. Some days it’s makeup free and tights, sometimes it’s dressed up with makeup, usually the latter when I need a pick me up.”

The rise of Stories has definitely had an impact on how we dress. Although they’re known for showing behind the scenes, we still want the scenes to look presentable. So women often throw on a nice dress or top and a dash of makeup before filming – even if it’s just for 5 minutes on camera.

Another prominent factor was mindset, and how dressing up can change yours. Yiota from Ola Digital Co made a valid point with her response: “If I’m in a bit of a funk, a bad mood or in a bad mental space I’ll wear nice clothes, do my hair and my makeup. It changes my mood so much! It can really alter my whole outlook on my day. I’d put it down to feeling more confident.”

There it is: confidence. The golden ticket of the feeling lottery. We all want it. We all need it to succeed. And some women are controlling how they dress to achieve it. Brilliant.

Lucy from The Little Content Co had a similar theory, and recommended I read Jen Sincero’s You Are A Badass At Making Money for further insight. “I am definitely more productive [when I] dress in a way that reflects the lifestyle I want – I love the working in a cafe lifestyle and bringing up my frequency [to match that].”

There’s another mountain to summit: manifesting your dream lifestyle by acting as if you’re already living it. I feel that’s a whole other blog post in itself, but one I’d very much life to write if you’d like to read it.

As I type this article, it’s Friday afternoon and I’m “dressed up”. I’m wearing a new top, a cute linen skirt and my hair is still looking semi-done after my appointment on Wednesday. I’m not wearing makeup, because my skin is acting out, but otherwise I feel “put together”.

Am I more productive? I’m not sure. I’ve been working for two solid hours and the inspiration is flowing. I haven’t been distracted and I feel good. Is this a direct result of what I’m wearing? I can’t say. Am I going to keep testing out this theory? Abso-fucking-lutely (if you know, you know).

One thing I (now) know for sure?

It appears that, given the opportunity, business-owning women are happy just to wear whatever helps them get the job done. For some, it’s activewear and stolen t-shirts (guilty), and others it’s cute outfits and styled hair. Despite the many advice-heavy articles on the internet, it really comes down to what works well for you and makes you feel confident.

A notion I can strongly support.

Until the next brew,


Viv + Team Rust


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