Playing favourites has its pitfalls. Be it mates, parents, or dare we say it, your kids, picking one over the other will only end in tears (not to mention a few months of expensive therapy).

Luckily, our clothes are made of tougher stuff, and singling out won’t result in emotional breakdowns. In fact, identifying a wardrobe hero is essential for developing a signature style. Here, we ask six menswear experts which piece takes first prize when it comes to the daily outfit selection.

Simon Chilvers

Men’s Style Director at MatchesFashion.com

“I’m fondest of a long-sleeved shirt by J.W. Anderson. In many ways, it’s totally classic apart from the oversizing. I’ve worn it on a couple of very significant personal occasions so it has important memories attached to it – all the clothes you keep for any length of time have the ability to make you feel something.

“I wear it with a white T-shirt and jeans, underneath an oversized sweatshirt with a peek of the hem below.”

Snail Embroidered Striped Shirt, available at J.W. Anderson, priced £227.

Snail Embroidered Striped Shirt

Olly Smith

Footwear Buyer at Harvey Nichols

“It’s really hard to pick an all-time favourite, so instead of looking to the past I’ll go with my most recent. And that has to be my Arc’teryx Veilance field jacket.

“It’s functional, understated luxury at its very best. Plus, it offers full waterproofing and the warmth of a heavy down jacket without the bulk – ideal for layering in winter.”

Arc’teryx Veilance Field Jacket, available at Arc’teryx Veilance, priced £900.

Arc’teryx Field Jacket

Jamie Millar

Freelance Journalist

“My all-time favourite has to be a shearling jacket by a traditional Swedish brand called Jofama. It cost around £350, but looks a million krone.

“Every consecutive year that I pull it out the closet – at least five or six now – I get compliments. Warm as hell and comfy as a heavenly cloud.”

Jofama Axel Leather Jacket, available at Zalando, priced £274.99.

Jofama Axel Leather Jacket

Olie Arnold

Style Director At Mr Porter

“I have a Helmut Lang denim jacket from his last ever collection, and I love it. It’s threadbare, and a little small – it was bought over 10 years ago – but I’ve yet to find one that is as wearable, or as cool.”

Helmut Lang Black Mr 87 Destroy Denim Jacket, available at ssense, priced £365.

Helmut Lang Black Mr 87 Destroy Denim Jacket

Neil Thornton

Content Manager at Harvey Nichols

“The best item I’ve ever bought has to be my AllSaints coat. It’s a long woollen overcoat with a large sculptural lapel – classic, but with a subtle modern twist.

“Two years after I bought it, it was stolen in Dublin (the booze-fuelled rant that followed was not my finest moment) and I opted out of a winter coat for months – nothing could rival my old favourite. But, almost three years later, I found another online and we’ve lived happily ever after.”

Iverson Coat, available at AllSaints, priced £365.

Iverson

Tom Courcey

Editor at The Idle Man

“Funnily enough, I’ve recently bought a leather jacket that’s quickly become my favourite. And it’s the most versatile piece of outerwear I own.

“Leather jackets are difficult to purchase – the fabric can be thin, or the shape unflattering. This time round however, The Idle Man’s own label has struck the perfect chord with a classic design and quality construction.”

Black Leather Biker, available at The Idle Man, priced £112.

Black Leather Biker