Which shoes are best for autumn? What does your T-shirt say about you? Where does one begin with jewellery? Contact us at asky@mrporter.com and we’ll do our best to sort out your style questions – or we’ll ask one of the world’s leading lights to shine the way. Welcome to Ask MR PORTER.

Tees are the undisputed MVP of any man’s wardrobe, no matter his age, and a great way to broadcast a message. We asked writer Mr Jason Diamond, author of The Sprawl and editor at InsideHook as well as a T-shirt fanatic to talk about his personal tee philosophy, for the best answer to your question.

“My general rule of thumb is this: T-shirts should be fun, but they should also tell people something about you,“ he says. “I’ve found that I can mix in a little modern streetwear, so some Supreme drops work for me, but others don’t; Online Ceramics is always a good bet, and sometimes I can still pull off a Stüssy shirt inspired by the design of the Frasier logo.

“For band shirts, I always go vintage. I like knowing the shirt comes from a time when I first loved the band. My absolute favourite type of shirt is the food-service shirt. I bought the Russ & Daughters tie-dye tee a few weeks ago, have two of the same shirt from Calumet Fisheries in Chicago, and I own multiple shirts from Rose Foods in Portland, Maine, even though I’ve only been there once. These days, with the challenges the service industry is facing, showing love is more important than ever.

“But really the most important thing is to make sure the T-shirt is something you want to wear and not something you just toss on to go about your day. It should make you feel good, and more like yourself.”

Please allow us to introduce you to some of the greatest shoes of all time, according to our US Editor: suede two- or three-eyelet boots. Soft on the feet, floppy and fun, easy on and off; they look great with jeans, a suit or even with shorts, if you’re cool enough. Chukkas or desert boots – with perhaps with a more autumn-appropriate rubber sole – are cordwainers’ greatest creations. 

Watching this year’s US Open and seeing all the incredible gold chains and pendants on Messrs Alexander Zverev and Denis Shapovalov made us feel as if men have been really missing an opportunity for self-expression, storytelling and memorialising an achievement. At any rate, those chains looked good and we, too, want to start wearing them.

As Rhude designer Mr Rhuigi Villaseñor told us a couple of years ago, he thinks of watches in the same way an athlete might think of medals. For him, watches are markers of achievements, and he treats himself to a little something to commemorate milestones in his life. A lot of men see watches in this way, as something to celebrate an occasion, or to be passed down from father to son. However, why not treat yourself to an accessory, instead?

Rings are certainly having a renaissance, and we heartily endorse the signet, with or without engravings or stones. The heft and blunt beauty of a signet ring face has an elegance that feels really relevant today. Similarly, beads have never looked better, in necklace or bracelet form. Our selection from Luis Morais will pair well with casual looks and smart tailoring alike.

Great question. Mr Steve Marks, owner of Persons of Interest barbershops in Brooklyn spoke to his senior barbers on the subject and is here to help.

“OK, so everyone grew their hair long during quarantine,” Mr Marks says, “and then decided to keep it that way because it was summer, the world’s ending and hippy hair suddenly felt fresh. But now it’s past Labor Day and it’s time to get real – even if you’re still working from home, you still have to show up sharp for Zoom. Floppy, don’t-care hair looks good on some guys, but definitely not everyone, because everyone’s got a different face shape. This is all part of our rigorous consultation process at Persons of Interest. There is no simple calculus, sadly – we factor in forehead height, hair density, hairline – but there are some simple rules of thumb to help guide you to a cut that suits you best.

• If you’ve got a round face

“A big floppy head of hair isn’t going to do you any favours. You need to tighten things up. Keep the sides squared, as this will help elongate your head’s shape and work against the roundness. Try a high taper or a classic gentlemen’s cut that’s kept slicked tight or short but is cut square; never rounded or with too much weight on the top. Think Seth Rogen in a super groomed moment and you’ll get the picture.”

• If you’ve got a long face

“With a more elongated face, you’ve got lots of options. You’ll look great with rounded crew cuts, French crops or a Keanu Reeves-style mid-length cut.”

• If you’ve got a square face

“If your face shape is on the square side, you can thank the hair gods because you can sport almost any cut and can usually pull off longer hair better than most. When getting a fade, opt for a high and tight with rounded corners to soften the squareness of your head.

“These general rules work for all types of hair whether it’s straight, wavy, curly or kinky. But as always, be ready to have a conversation with your barber and if you come armed with a photo of what you’re trying to achieve, all the better.”