Dad Dresser: How To Boss The School Run

Esquire's Senior Fashion Editor picks five pieces to up your casualwear game

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It’s been 12 months since I moved my wife, two small children and our whippet out of London. A year that’s tested our judgement on moving out of the metropolis. Settling the kids into a new school, getting to grips with oil central heating.

Stepping in cow shit on a regular basis (we live next to a farm) and dealing with a much longer commute into work. An extra 160-mile train commute to be precise. – Painful doesn’t even get close. You see, we didn’t just move counties. We moved countries. I now live in Wales.

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Not the must logical of moves I admit, but we had our reasons. Naturally I can spout on all day about the merits of this seismic lifestyle change. The kids? They’re really flourishing.

Weekends? So relaxing, we’re only 10 minutes from the beach and it's all so much cheaper. While most of these observations are true, what I won’t be shouting about is how I’ve moved to the epicentre of hipsterdom.

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This small picturesque Welsh town ain’t no Shoreditch. You’d be lucky to find a slim denim jean within a 10-mile radius, never mind one neatly rolled up to reveal a colourful sock. Not a whiff of a double-breasted soft shoulder jacket. Zero. Zilch. 

As for a double monk-strap shoe? That’s something you’re more likely to find at the local monastery. This observation comes into sharp focus, when on the odd day I take my children to our local primary school.

No man still needs to be wearing frayed boot cut jeans. And even though there has recently been a comeback for the combat trouser, my fellow fathers are still wearing the originals, which give the impression that their arse has just fainted – all baggy and shapeless.

I did the school run more often back in London, where men could spot a Japanese selvedge denim at 10 paces, there was a common language in the clothes we wore.

Admittedly, many of my fellow fathers were ‘those media types’ so there was a certain amount of creativity in the way we dressed. I still do. I certainly hadn’t paid much notice to any particular distinguishable feature in my daily choice of outfits.

Working in the heart of London’s Soho is swamped with the most astutely dressed men you are likely to find anywhere on planet earth. You simply don’t stand out in your Savile Row suits or the current hipster label kicking up a storm in East London. I took all this for granted.

Until I moved out. Now I feel like the outsider. I can feel the chorus of my detractors through pursed lips at the school gate: "Nobody dresses with that much care and attention unless they’ve got a job interview or a court appearance. Or is gay."

I won’t be changing my style anytime soon – hell, it’s taken me 40 years to discover what I actually look good in.  So, with my new fellow countrymen in mind, here are my top five essential pieces for update your casual wardrobe and improving your fashion credentials just in time for that next parents' evening.

1 | Slim-fitting Jeans

J Brand Slim/Tyler & Mod, £183


2 | Barbour Jacket

Flyer Waxed Jacket from the Steve McQueen™ capsule, £219

3 | Check shirt

AMI Slim-Fit Check Woven-Cotton Button-Down Collar Shirt, £160


4 | Tailored Jacket 

Oliver Spencer Berwick Jacket Ancroft Blue, £310


5 | Brogue Lace-ups

Grenson, Stanley with rubber thick lightweight sole, £200

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