Easy wins: no one knows what we’re supposed to wear, so dress like a seven-year-old

It’s 9pm the night before you are due to meet friends for a long-awaited catch-up, and a tentative message appears in the group chat: So, uh, what are we supposed to be wearing now?

Two years spent mostly indoors has killed the art of dressing. My style references since March 2020 have been hip teens on TikTok, who lately are looking like they just walked off the set of underrated 2000 teen classic Whatever It Takes, and the five-pack of men’s flannelette shirts I got on sale.

No one knows what we are supposed to wear. What we used to wear, as adults with professional jobs, is both uncomfortable – so many waistbands! Such narrow heels! – and, at this point, not even cool.

But before you go out to buy an entirely new wardrobe of elastic-backed slacks in some kind of classic bone to pair with an oversized blazer in an attempt at post-Covid office casual, consider this: don’t.

Instead, try dressing in the clothes you really enjoy.

This does not have to mean embarking on the introspective and often fraught process to determine your personal style, which can be great fun if you are into clothes and up for being negged about your proportions by a New York style consultant, but can also be quite stressful. What if, after your serious consideration, you discover that your personal style is deeply boring? Best not to risk it.

The easiest way to determine what clothes you actually like wearing is to think back to a time when you had the highest level of personal choice over your outfits relative to your awareness of outside opinions. For me, this was about age seven.

When I was seven, I wore elastic-sided jodhpur boots with all outfits at all times. I liked stripes. I liked orange and acid green. I did not care whether things were flattering to my body shape because I did not have a shape.

Now, at 34, I have four different pairs of elastic-sided boots and am considering getting a fifth. No one has questioned whether this is appropriate. We are living through a traumatic, world-shaping event. We should be able to do so wearing overalls if we wish.

Old friends may do a double take when you turn up to brunch dressing confidently like your seven-year-old self. But then they’ll lean forward and ask: “Is that what we’re wearing now?”

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