The Dress-a-Day Challenge

When I was at university, I wore dresses every day. Cheap babydoll numbers from Primark or Topshop with the generic ankle boots that every other person sported at house parties. “I’m not a jeans person” was my go-to phrase.

And then post-college, it flipped. But why?

It’s hard to find original dresses that stand the test of time and more importantly, fit into a work environment. Beach dresses are a dime a dozen; I have a whole stack that work well when nestled against warm skin and a piña colada, but they don’t quite translate on The London Underground or next to the woman in the suit blocking the photocopier.

I knew there had to be a solution, so I set myself a twofold challenge: 1) wear a dress every day of the working week and 2) see if I still feel like “myself” while doing it — because how do you make a dress your own so that the second time it’s worn doesn’t feel like mere repetition?

For me, it’s about variable details: changing the shoes, the hair style and the belt. Pretty simple, but then, that’s the beauty — dresses are simple.

Monday

Mondays are for non-restricted waistlines. I’ve been through more denim pinafores in my lifetime than Leo has Victoria’s Secret angels. My current favorite is this ASOS one with a frayed hem.

Vintage blouse, ASOS pinafore, Converse sneakers, Theodora Warre earrings

Tuesday

As worn by Alexa to Topshop Unique’s SS15 show in February, this dress was destined to be a top seller, even if she hadn’t lent her gamine form to its mini proportions. I first wore it in my column for The Sunday Times Style and knew I had to have it — the florals are “non-naff*” and vintage-esque (surprisingly hard things to achieve in a dress unless it’s actually vintage or super expensive — though if you’re willing to shell out, Vilshenko and Saint Laurent do florals well.)

Topshop Unique dress, Uterqüe heels

Wednesday

That aforementioned stack of beach dresses includes a lot of white ones (Temperley London, Topshop, Juliet Dunn, Mango, Isabel Marant — list goes on) but not a damn one of them are suitable for any water cooler office moments. I found this Karen Millen one and I think it fills a real gap. Incidentally, if you are familiar with the brand, it’s done a massive turn-around recently. The re-branding has resulted in a much more expensive but infinitely cooler Karen Millen.

Karen Millen dress, Diesel belt, Sandro fringe bucket bag, Topshop sandals

Thursday

This dress makes me feel unfathomably like Kate Bosworth. And these shoes are my favorite; they look like Céline. I feel so empowered by this outfit that I look distinctly (and equally unfathomably) haughty. I’ll come back down to earth as soon as I take it all off. Promise.

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Vintage denim dress, Uterqüe shoes and Hermès neck scarf

Friday

Friday’s child going off to a party! I’m biased because it’s my best friend’s label but these are the comfiest, sexiest dresses — fact. Adwoa Aboah, Clara Paget and Georgia Jagger are also fans. If you’re not into body-con (and I’m not, normally) then check out the crinkle-stretch swimwear (as worn by Julia Roberts in Pretty Woman).

Hunza G Dress and Saint Laurent shoes

Saturday

Cooling down on a Saturday. 6 dresses, 6 days, complete!

Claudie Pierlot jacket, vintage bandana scarf, slip dress and belt, Superga sneakers.

If the challenge taught me anything, it’s that you WILL flash your knickers at some point during the day. And that I am totally resolved to wearing more dresses.

*British slang vocab lesson: non-naff = not tacky or cheesy. Follow Pandora Sykes on Instagram and Twitter.

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