Deniz Hassan in shorts with flichart

‘Punk had just started, and no one wore shorts – except me’

Dick Stringer, 71, artist, Whitstable/Greenwich

It all began when I was sent to England’s cheapest boarding school, aged 11 – total bill for the first term, including board: £63. As the family finances were under strain, Mum managed to get a secondhand schoolboy suit for my uniform. The worst aspect of it was the long shorts, which came down below my knees and had fly buttons made of casein, a sort of rubbery plastic produced from milk protein. It was compulsory to wear shorts then, so I just had to make the best of it. You would have thought this would put me off, but we didn’t have central heating back then, so I probably just became accustomed to being a bit cold. Now I don’t feel it at all.

I got into shorts properly when I went to art school. Punk was just starting, and no one wore shorts – or at least no adults, only runners, who preferred those dinky little sporting ones.

In the wonderful, long, hot summer of 1976 I was studying at the Royal College of Art and discovered Laurence Corner army surplus store, with its supplies of It Ain’t Half Hot Mum shorts. They were quite long and baggy, with double buckles, and in a sort of khaki colour. They were just a bit different from all the flares. I wore mine with jelly shoes and screen-printed T-shirts. Soon, even the girls from the fashion school were wearing them. I think we all looked fantastic.

Today, I’m in shorts most of the time. When you work for yourself you can wear what you want. My work is quite physical – we have a factory in Greenwich full of old machines and we make all sorts: chandeliers for cruise ships, window displays for John Lewis, architectural bits for Antony Gormley. We work with saw blades, so I have to wear sensible shoes, but the worst injury I’ve sustained is from a broken coffee cup.

I now have about 20 pairs of shorts, though my wife is in charge of buying them. I do, of course, possess the odd pair of long trousers, and my wife insisted that for our daughter’s wedding I wear my suit from tailor Charlie Allen – I had asked Charlie to make me a pair of shorts but I won’t trouble you with his reply.

To me, shorts represent a wonderful sort of freedom. The best thing is riding around on my motorbike with the wind whistling around the parts – folks say it’s dangerous, but since I consider 35mph a merry clip, I think I’m OK.

Deniz Hassan at work. Photograph: David Newby/The Guardian

‘If skirts were more of a thing for men, I’d wear one of them’

Deniz Hassan, 41, nonprofit fundraiser, south London

My relationship with shorts initially stemmed from the fact that I cycled a lot, and wearing them stopped me getting bike oil on my trousers. Then it just sort of snowballed. At one point I was changing into trousers when I got to work: I kept them rolled up in my bag so I looked pretty creased. Then I just stopped out of sheer laziness. Now I exist in shorts – unless I have to look acceptable.

I’ve had pushback, of course. I work in nonprofit fundraising, mostly with NGOs. At one point I worked for the UN World Food Programme, and shorts were deemed unacceptable. During that period I kept a pair of trousers with me permanently. But most clients don’t mind. It’s about reading the room: if it’s a corporate client I will stuff a pair of trousers in my bag.

I think employers today understand that it simply doesn’t matter what you wear; your output is far more crucial. Fifteen years ago it was a different story – for men, the only point of differentiation was whether you wore a tie or not. It was stuffy. Now people work from home, anything goes. Frankly, if skirts were more of a thing for men, I’d probably wear one of them.

I wear chino shorts, and I churn through them. The crotch wears out pretty quickly. I have about five pairs for activities and eight pairs of smartish ones that are in different conditions of wearability. Some are almost indecent – I worry that on the bike I’m borderline flashing. I wear sandals in summer, and trainers with an interesting sock in other weather. Nothing too overthought.

I don’t seem to experience the cold. Would I wear shorts in the snow? Absolutely. Of course, it matters what else you’re wearing – I find that shorts with a big winter coat can make you look like an idiot.

Philip Gager outside church in shorts
Philip Gager wears shorts to church on Christmas Day. Photograph: David Newby/The Guardian

‘Legs dry quicker than trousers’

Philip Gager, 77, retired academic living in the north of England

When I’m out and about, people stop me because they recognise me as the man in shorts. On Christmas Day, when I’m in church, they check that I’m wearing them. I always am. I can’t let them down. Even when I was working, I would change into shorts when I got home. This was the 1970s. I taught maths, and it wouldn’t have been deemed proper to turn up in shorts to teach. But now I’m a governor at a local school and I wear shorts to meetings. Whether I’m breaking the rules or not, I don’t know – I’m old enough to not worry.

There are lots of reasons I like shorts. One is the freedom. With trousers, I just hate the flapping. And have you tried kneeling down outside? Or what if it’s raining? Legs dry quicker than trousers. It saves washing too. You just have to mind the nettles.

I don’t get cold. My mother was wearing skirts with no tights at 95, so it must be in the genes. One time, though, I went to Finland. It was the end of February. We were at Helsinki airport waiting for a bus, and I was wearing shorts. It was -15C. Then, and only then, I said: “It’s a bit nippy.”

I also wear shorts whenever I go walking or fell running. With orienteering, it’s a bit tricky. Often we’re not allowed to wear shorts because you’re fighting through gorse and bracken. Then I have to wear leggings. If I’m high up, I carry spare trousers in case something happens.

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‘You can’t ask someone for their vote in shorts – even the Greens’

Thom Robinson, 36, tree surgeon and local councillor, Darlington

I wear shorts 365 days of the year. I’m originally from Barnard Castle and wore shorts a lot growing up, but it gets quite cold up there. Then, a decade ago, I moved nearer to the coast, where it’s about 5C warmer, so I started wearing shorts all the time. I’m now a Darlington borough councillor and a tree surgeon, and I’ve found shorts work for both jobs.

The truth is, I just find trousers uncomfortable: the general restriction around the lower leg, particularly when they get wet. I’m also a warm person. I don’t know if it’s medical but I’ve been told I’m like a nuclear reactor in my core.

I have a standard set of “dress” shorts, as I call them, in chino style, and I also have rougher ones for outdoors stuff. I have a few pairs of trousers and one suit for wearing at weddings or funerals. I am considering getting it tailored into shorts, though.

There are times when I have to wear trousers: usually when I’m canvassing, because I need to look more official. You can’t ask someone for their vote if you’re in shorts, even if I am in the Green party. But I’ve done council meetings, quite formal ones, in shorts, and no one has batted an eyelid.

I always wear shorts for tree surgery. You’re supposed to wear Kevlar trousers, which is basically PPE, or a bulletproof vest. The material has thousands of strands and if the chainsaw lands on it, the teeth get dragged into the mechanism and jam it. It stops your leg getting chopped off. But when you’re well trained and you have the correct stance, it’s almost impossible to cut yourself. What can I say: I live life on the edge.

‘Teaching years 1 and 2, you’re basically crawling on the floor – you don’t want trousers for that’

Oli Lougheed, 41, teacher, Marple, near Manchester

I wear shorts all year round, but only when I’m not at work. I’m a primary school teacher so I’m not allowed to.

I used to work in a school where initially I could – they didn’t outlaw shorts, just denim. I had to dress smartly, which I took as wearing shorts and smart shoes and a shirt. But, in the end, they asked me not to wear them any more.

Working in schools is insanely hot. It’s full of kids, there’s no aircon, and we only shut the windows when it starts to cool down at the end of the day. It doesn’t make sense to wear anything but shorts. You’re also always on your feet. Teaching years 1 and 2, you’re basically crawling around the floor. You don’t want suit trousers for that. They’d just be covered in glue.

It’s weird that people get shocked. Women show a lot more leg. If I wore the equivalent of a skirt to school, people would be horrified. I just think: use your judgment. I definitely look smarter than someone in a weird suit and unbuttoned shirt. I have other rules: never wear sandals, and watch your socks.

Growing up, I wore shorts until I went to high school. I really hated school trousers. Our kids also wear shorts in all weathers. My sons have a choice, of course. We bought the older one some trousers, but he was like, “Nah”. The younger one wears them a bit. But it’s mostly shorts, even when it’s pretty cold.

I used to cycle every day, and I guess that’s why I started. My commute to work was through a forest, and my trousers got filthy. I’ve never looked back. I prefer shorts with a bit of stretch, ones that look tailored, smart, but if I need to jump on my bike I’ll be wearing the right thing. Other than that, it’s normal-people clothing up top: a jumper and a coat.

If I was going to be outside, standing around for hours, maybe I’d wear trousers. But, to be honest, I wear shorts in the snow.

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