The Casual Workplace Challenge

When I first started working at a SaaS technology company, I was floored by how chill everything was. Between dogs in the office, a volleyball court in the backyard, and a super casual dress code, I was pretty much in work heaven. My first week there I dressed business casual (as I had been taught to do in business school), but eventually stopped when I realized that my boss, who usually dressed in jeans and a nice shirt, had also started dressing up and wearing blazers and I felt bad.

Flash forward almost 3 years, and it got to the point where I had pretty much given up on dressing nice. Between the freezing cold temperatures and a slightly longer commute due to moving in with the boyfriend, it was just “too much effort” to put in the effort to look more than just ok on a daily basis.

Which brings me to the challenge that I put myself through this past week, on one of the coldest weeks of the year (with temperatures hovering between -10°C to -25°C), I decided to dress up all week. No jeans, AT ALL. Here’s how it went!


I didn’t actually officially start this challenge until Tuesday, but I still participated on Monday (whether I knew it or not!) with a chiffon Portofino blouse and mid-rise skinny legging pants from EXPRESS. While I was miffed by the lack of pockets, I liked being able to pet the work puppies without getting fur all over me.


Tuesday morning I woke up and remembered how much I liked how I felt when I didn’t wear jeans the day before, so I stepped it up and went back deep in my closet to the clothes I haven’t worn in years. All that business casual wear. On Tuesday I wore a barcelona cami, low-rise bright orange columnist pants, and a cardigan, all from EXPRESS again. This outfit was a little more casual, and I’ll admit that the pants were a little hard to get on, but I received so many compliments throughout the day about the pants that it was totally worth it.


Tuesday night, between work and a work function, a colleague and I went to Marshalls, which was a super bad idea because we are both horrible influences on each other. I ended up buying a pair of light blue Hunter boots and a new dress from Tommy Hilfiger that I didn’t even try on. When I got home that night I tried it on and since it fit great, I decided I wanted to wear it on Wednesday, upping the faniciness level once again.


Getting real here for a sec, I didn’t want to do the challenge after Wednesday. I had already posted about it on social media, and I had a horrible night sleep. I wanted to just throw on jeans and a t-shirt and brave the cold. I was in a bad mood and just needed a hoodie dammit! But nevertheless I still kept up with the challenge and went for a cross-over bodysuit from Dynamite under some high waisted palazzo pants from EXPRESS. I paired it with fuzzy socks and my super broken-in pair of sparkly polka dot Keds because I’m not perfect, and also you can’t see my shoes or socks underneath the pants anyways because I’m short. And yes, I did change into heels just for the photo.


I met the boyfriend at the mall after work on Thursday night and while walking through Saks off Fifth we started looking at cashmere sweaters. Now, the boyfriend wears business wear every day for work so he has a large collection of button down shirts and cashmere sweaters, which are pretty much his staple during the winter. He saw this cardigan and thought of me, so he bought it for me as a belated 29-month-aversary (since I told him he needed to have a reason for buying such a fancy sweater for me!). I paired it with a portofino shirt from EXPRESS and a pair of leggings from Lululemon since I didn’t want to pretty much rewear the same outfit from Monday. Also, it was Friday and I wanted to dress down but class it up. I paired it with my favourite ballet flats ever.

End of week recap

Overall, this was a fun experiment! It definitely made me “shop my closet” more, and wear pieces I might not’ve otherwise worn. I think it helped my motivation buying new pieces throughout the week, since I don’t really buy new clothes all that often. I liked dressing up for work, and the response I got from my colleagues was all super positive. They noticed the effort I put into what I wore, and a couple of them even joined in towards the end of the week. We might even make “Work it Wednesdays” a thing from now on!

While I really liked dressing up, I can’t deny that I didn’t wear the most practical outfits throughout the week, as -15°C weather doesn’t really allow for many nice dresses or thinner pants.

This challenge also had ancillary benefits, most notably that I’m now not as shy to ask my lovely coworkers to take photos for me for my Instagram. I also have more photos of myself in general to use on social media, which is a problem I’d actually noticed I was having. I wasn’t posting as much because I din’t want to post the same kind of thing over and over again, and there’s only so many selfies you can take before you look like you’re too afraid to ask anyone to take a photo for you (which like I totally was, but whatever).


What happens next?

Would I do this again? Yes, definitely! Will I be wearing jeans next week? Also a yes. I liked the challenge but the weather here really isn’t practical for dressing up. I definitely want to make more of an effort in the future (and actually wear all of my business casual clothes!), but it’ll be nice to be able to wear jeans again for the days when I feel kind of like crap. Maybe I’ll do a spring or summer version of the challenge once the weather gets better and see what the difference is!


What’s your work wardrobe like? Do you have to wear business casual, or casual casual?

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