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“I Dressed Like My Boss For A Week — Here’s What Happened”

Posted on: by Michelle October
Michelle dressed like her boss for an experiment

Sneakers of procrastination or patriarchal heels of doom? Staff writer Michelle dressed like her boss for a week to find out. 

We know you’re supposed to dress for the job you want. But dress codes are starting to mean less and less, and around the Women’s Health HQ, dressing for success means donning a pair of leggings and your fave trainers. So when we tasked our stiletto-obsessed editor, Dan, to swap shoes with Michelle, the trainer-devoted staff writer, even we weren’t expecting the results.

The Challenge 

Dan, Editor of Women’s Health  

I confess: my love of heels is not a passing fancy. I wear sneakers between my car and my yoga studio. And that is pretty much the sum total of my affection. Don’t get me wrong: I love a pair of sneakers… In much the same way as I love any pair of shoes – with an adoration that is borderline stalker. I just don’t wear them very often. Like my swirling boho gypsy skirt, lust does not always equate to wanting to leave the house dressed like Stevie Nicks. I cannot take Work Me seriously in sneakers: I bounce around… I shoulder bop like a Hanson brother. Anyway, my team cares little for this psychological insight and sets me and The Office Millennial a task: swap the heels for sneakers. And in the case of TOM – the sneakers for heels. Incidentally, she seems as rocked by the suggestion as I am.

Michelle, staff writer at WH 

My gripe with heels is probably pretty wacky, I’d wager. I’m all about utility: tie your hair back to focus, wear a sling bag because you can do more with your arms, ditch the make-up because it runs when you’re at the gym. See? I even rejoiced after losing some weight and along with it, my boobs. My reason? Less jiggling around when I’m busy! So around the office, it would be a rarity to see me sauntering in on a pair of stylish daggers. You can’t run away from murderers in heels. Added to that, outfits are way easier to pull off when there isn’t a pair of patent-leather stilettos attached to the deal. My boss, Dan, is of an acutely opposite opinion. We couldn’t be more Miranda and Andy if we tried. And so here we are.

Day 1


Day One dawns. My phone beeps… “My calves are already aching but I am wearing heels. Don’t forget the challenge!” Mercifully, I am already on my way to the office. Not-entirely-sensible coral red heels accounted for…I want to Google “what would Jenna Lyons do?” I know she’d add sequins and a roll-up. Tomorrow, I am bringing full Jenna.


I’m wearing a pair of vintage kitten heels I found at a second-hand store, which I fell in love with but obviously never wore. (Where to? For what occasion? Ballroom practice?) I stagger into the office, looking like a toddler dressing up in mommy’s clothes. Dan, cool as a cucumber in orange heels, has forgotten about the challenge. I feel like maybe this challenge was a ploy to get me to dress better. I feel self-conscious. If it isn’t the click-clack announcement of my presence, it feels as if being that artificially tall makes me overly noticeable. My (facial) cheeks are on fire every time I stand up.

A photo posted by Danielle Weakley (@danweakley) on

Day 2


Disclaimer: I did not bring full Jenna… It is 33 degrees outside. Even I wasn’t prepared to cuff my jeans and roll up my shirtsleeves. Too. Damn. Hot. So I defaulted to what any self respecting fashion girl would do and I found the loudest, brightest, most OTT clutch bag I have in my collection to offset the quiet preppiness of the grey suede Reebok Classics and my LBS. It takes hours of being at WH HQ before I stop skipping between meetings and moonwalking out of offices… I have a long way to go before I’m used to sneakers. Clearly. The upside is that my daughters think I look super cool and Instagram is lusting after my Reeboks, so, like, #winning. And Michelle failed on a technicality because #wedges, not #heels. #Gratitude


I have not failed. Yes, they are wedges, but I still feel unnaturally tall and unbearably self-conscious. I didn’t fall head-over-heels (ha!) for these black wedges, but they were the only shoes with height I felt comfortable buying, and would ever wear. Having said that, I’ve only wore them twice. Despite my aversion for being noticed, I do feel pretty and spend the day swishing around in the wispy dress–shoes combo. I feel like Belle, if she ever bothered to wear anything other than that ghastly mustard. Cute? check. Practical? Uncheck! I still can’t run away from psycho stalkers.

A photo posted by Danielle Weakley (@danweakley) on

Day 3


I realized I couldn’t Kim Kardashian Monochrome the entire week, so I pulled out the red Adidas Pure Boost. Someone told me yesterday that I was using the clutch bag to run interference for the sneakers, so I thought I’d hone that approach… Statement clutch. Check. Blazer. Check. Pushed up sleeves because temperature of molten lava outside. Check. And we’re off. I seem to have slowed down on the skipping, which is an altogether good thing. Totes getting the hang of this sneaker thing.


I pull on my favourite (and ironically highest) pair of heels yet: a brown suede pair of chunky heels I bought for a wedding and – duh – never wore. Because we’re being brave this week, I pair mine with (gasp!) a mini skirt. I take a look at myself in the mirror and I must confess: I look so put-together. Kind of like how you’d look as a working woman, and not as my usual Dobby-discovers-sock aesthetic. I am unnerved. The old, creepy men on the train are ecstatic. I am uncomfortable, to say the very least. But I make it to the office and everyone applauds my newfound style. It bolsters my confidence; maybe running in heels isn’t the point, after all.

Day 4


I’ve now fully recalibrated my working wardrobe to match my kicks. Today’s white adidas CrazyTrain are unflinchingly Ivy League, but all white sneaks have a way of making a monochrome look pop, so it’s back to single colour everything else for moi. Thanks KK. I am a little bored. The playfulness of sneakers was fun, and I was feeling younger, edgier, snappier and got lots of comments. But that feeling is wearing away and I need those heels, stat.


I did not think I’d make it out the house today. After scavenging at the back of my wardrobe for a full ten minutes, I pull out a long-forgotten turquoise chunky heel. I pair them with jeans because it’s chilly out, and spend a further ten minutes rummaging for a blazer, cardigan, anything to find a lick of polish. As The Office Millennial, I pride myself on my collection of puffer jackets and gym jackets. No blazers here. I pull out an ancient 80’s blazer from my mom that my sister and I would wear ironically. There are way too many buttons going on but somehow, the heels make everything look better. Suddenly I like the look of my legs in these jeans; without the heels my hips seem to expand outward. Is it a play on my senses? Is it a mirage? Was Dan right all along???? I am now in the throes of an existential crisis.

Day 5


So, I almost fell off the wagon. So what? In my fast-ass sneakers and I would have totally caught up with it anyway! I’m definitely over the trainers today. I’m bored of being playful. Sneakers are great in some aspects of work life; but there’s a level at which heels help out you in a different mindset: you stand up taller, and own your space more. So I’m happy to be in heels again soon. But we’ve decided to do the swap once again, once a week. Here’s to Sneaker Wednesdays… Yes, Wednesdays… Not errrrday. Just Wednesday. I like it.


I have one last pair of shoes to wear, and when I glance at myself before getting in the car (still figuring out clutch control with those heels), I feel… good. Yes, I am moving at an annoyingly glacial pace, but I look polished, pretty, put-together. There’s something to be said for looking great that affects how you look. After I read Dan’s words on Jenna Lyons, I Google her and am affirmed by what she says about style: “Sometimes people assume that what you wear isn’t important but I know it can make someone who needs a little boost feel beautiful.” I’m strangely enamoured by this. I probably won’t wear heels religiously, but the swap threw me sufficiently into the deep end and gave me a shake-up. On Wednesdays we wear heels? I’m ok with that.

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  • Lois Carol Wessels

    Loved the article!