The rules for pulling off autumn hats like David Beckham

When up early with his chickens on a sunny autumn morning, David Beckham reaches for a few key country accessories. A pack of four little dogs, to take on the rounds at his Cotswolds estate. A wooden walking pole; or is it a shepherd’s crook? Always, though, a baker boy hat – the tea cosy of men’s millinery – in a suitable checked felt fabric.

The baker boy has enjoyed a surge in popularity in recent years – but it isn’t the easiest look to pull off. There are unspoken rules for wearing one, from the dimensions, to the rest of the outfit, to the environment you take it to.

Beckham posted a picture of his “country life” look on Instagram and it’s clear that he understands the fashion nuances required to wear the hat, rather than allowing it to overpower him.

This style works for midlife men who have a bit of ruggedness to their look. Too perfectly clean shaven and you’ll read as a country faker; too much facial hair and you run a hipster craft brewery in East London. Too young and you’ll look like a chimney sweep, too old and you’re Del Boy’s Uncle Albert.

“Both a baker boy and a newsboy hat were invented to be cost effective hats, cheap to buy so that, yes, newspaper boys and bakers could afford to wear them,” explains Jayesh Vaghela, master hatter at Lock & Co. Hatters and a hat expert on the BBC’s Repair Shop. “They are made up of eight panels, which could be from any mixture of fabrics, with the height at the crown.”

The baker boy offers more volume on the top, while the newsboy is more tapered, and a flat cap, literally, lays flat, made with a single panel on top.

Vaghela explains that the first thing he considers when selecting a new hat for a customer is their height and frame. “You don’t want someone to be over-hatted, nor under-hatted,” he says.

“A man with a mid-height and frame would suit a baker boy, as they can handle that slight extra height,” he notes. “A thinner face might better suit a newsboy style, as the tapering would work with the sharper outline of facial features. The safest for all face shapes, including rounded, is a flat cap. Assessing that proportion is crucial, as you always want to wear the hat, not have the hat wear you.”

Historical baker boy pin-ups span Robert Redford in The Sting, to half the cast of Snatch (throw in the director, Guy Ritchie, too for good measure). Characters Derek Trotter and Tommy Shelby have contributed to this idea that you need a rough edge to wear one, while on the red carpet, or at race days Mike Tindall and Idris Elba have shown it can be polished up and worn with a tie and a smart coat.

While the baker boy can look good with a herringbone jacket, or a cord blazer and jeans, suiting is perhaps not its easiest natural partner. Sportswear, meanwhile, should never be seen in the same look.

A denim, plaid, or chambray shirt like Beckham’s will provide the perfect smart-casual foil – just add smart brown Chelsea boots. Lock & Co.’s baker boys are an investment piece that will last for decades in your wardrobe, a factor that is reflected in their £200-plus price tags.

That said, they are properly sized to fit you, and come in luxury materials from cashmere to British wool tweeds, fabrics that will never go out of style.

On the high street, Barbour, Moss and Holland Cooper all offer great selections of patterns and colours. Pick something in autumnal hues, or in a classic check like a Prince of Wales or herringbone, to ensure your look is timeless.

The final rule for wearing a baker boy hat, whoever you are, is to think about where you are wearing it and who you might be meeting.

For pub lunches, long walks, and outdoor events in the winter, this style comes into its own. But if there’s a chance you might meet a friend, or three, who could all be wearing the same style of hat, think twice.

Fine for a meet at Cheltenham, but taken out of context and spotted at an inner city Pizza Express, and you may well look like a pack of Peaky Blinders extras who have wandered off the set.

Highgrove Baker Boy Hat, £365, Lock & Co

Prince of Wales baker boy cap, £79, Holland Cooper

Claymore baker boy, £37.95, Barbour

Herringbone baker boy, £39.95, Moss