It’s not that I haven’t considered it, flip-flops make sense. They’re a practical solution to regulating your temperature in the sweltering heat of summer. I get it. But writing to you now is someone who’s spent most of their adult life envisioning, putting together and talking about aesthetics. So how could it ever make sense that I would wear flip-flops? Remember that famous Karl Lagerfeld quote that says wearing sweatpants is a sign that you’ve given up? I’m afraid to ask what he thought about a plakkie.

Then came my stint working at a tech startup, where flip-flops are a trans-seasonal staple among a pack of software developers. They moved in large groups hunting for solutions, gathering data, preying on tech bugs (can you tell I have no idea what they do), accompanied by a constantly roaring flippity-floppity soundtrack heavy enough to match the percussion section of an orchestra.

All this to say that this writer could not in good conscience tell you how to wear a flip-flop without ever having worn a pair himself. So I took five days to wear them every day, no matter where I went or who I was seeing. Yes, it was stressful. No, it wasn’t a brilliant idea. Yes, I am better for it. Read why.

Day 1

The agenda: Work from home
The fit: Nine times out of ten my at home uniform is head-to-toe black. Someone once told me it’s about my need for people to perceive me as being in control of my environment, they weren’t wrong. There couldn’t be a more fitting way to take my first steps into the unknown territory that is flip-flops.
The reaction: After quite an awkward day of trying to lift my foot to camera height for people on the other end of zoom calls to see, the general reaction was… unbothered. I guess flip-flops at home isn’t an earth-shattering idea.
The conclusion: Overall win for practicality, comfort, being suited to the environment and the ease of slipping on when your lunch order arrives. A word of advice if I may – don’t show people your toes on a work call.

Day 2

The agenda: The Brainstorm Meeting
The fit: Tonal in beige, oversized cuts. My rationale here was that the only way I was going to get away with wearing flip-flops to a meeting is if it was part of a statement look. Luckily the chino does the work of playing up the formal element, while the rest is quite relaxed.
The reaction: “Are you going to the beach later?” That’s good, right?
The conclusion: I never thought I’d say this but it is possible to be polished and put together in a pair of flip-flops. I wouldn’t dare try it in a serious meeting with clients or the boss, but you let me know how it goes.

Day 3

The agenda: The Coffee Meeting
The look: Scandinavian streetwear-inspired basics. A navy boxy tee, wide cut trousers create an effortless silhouette. Signature accessories make the look intentional and considered.
The reaction: “I didn’t even know you had toes,” the photographer that I met up with joked.
The conclusion: It can’t be explained why wearing flip-flops in a coffee shop gave me more anxiety than wearing them to a meeting. The clapping sound as I passed people sitting by their laptops definitely attracted a few criticising eyeballs. This writer would not recommend.

Day 4

The agenda: Entertaining at Home
The fit: Relaxed olive green chino and light knitted tee with matching green flip flops. Dialed it all the way down for this one so that the friends coming over would feel comfortable and relaxed.
The reaction: “I’ve never seen you look so honest before,” which I still think might be a little bit of an insult, but I’ll take it as a testament to how your exposed toes really do make people feel like they know you.
The conclusion: People will love you for it. Bold, I know. I never thought a flip-flop would evoke an emotion either. Be careful, though, of the sticky spills on your foot as you get increasingly drunk and be prepared for the chance that you may have to walk around barefoot after a few drinks and that people may perceive you as unravelling because of that. It might be a good idea to switch to closed shoes at 11pm.

Day 5

The agenda: Beach day
The fit: Printed resort shirt, swim shorts and a hat – the only way to beach, surely. I took a risk and went for the boldest flip-flop yet, because I was confident nobody would notice them at the beach otherwise.
The reaction: My risk was met with “Wow! Yellow.” Think of this statement as more of a question and not like a statement at all. The question is “are you sure?”
The conclusion: A word of advice – wear bold colours with total conviction. As it turns out bright flip-flops have a way of offending people, so wear them like no one is watching (or when no one is watching).

Akim Jardine – MKM guest fashion editor