It is a mad, mad, mad world, and MR PORTER is here to help. In this column, appearing fortnightly, we – with help from our friends and family of experts, insiders and wise sages – will answer your most pressing questions on style, etiquette, wellness, grooming, the workplace and everything else besides. Have a question? Drop us a line at asky@mrporter.com and we’ll do our darnedest to sort it out. Welcome to Ask MR PORTER. 

Well, yes, and we cannot think of anyone better to answer this than someone who has been the menswear world’s voice of his generation (now approaching 40). Mr Lawrence Schlossman, the writer, editor and now shock jock co-host of podcast Throwing Fits, has made a career of obsessing over and lampooning streetwear brands, its grails and enthusiasts. No one, in other words, takes the topic more seriously, or talks about it more sarcastically, than Mr Schlossman. To wit: “Wearing streetwear at 40 may very well be as clear a sign as any that you have deeper emotional issues that need addressing first and foremost, as is customary with any midlife crisis. But I am going to suspend belief since my chosen profession is talking about clothes and not your paralysing fear of what legacy you’ll leave or whatever else is keeping you up at night.”

To the business at hand: “You want to wear streetwear and be cool, but you’re old and have some semblance of self-awareness. So, what do you do? Depending on how much of a fixer-upper you are, please promptly neutralise any and all clothing with huge logos and overt branding, not forgetting any sneakers that if you squint look like they were designed for babies. Now you have a clean slate and can lean fully into the tastefully spicy world of ready-to-wear grown-man streetwear, which a lot of your favourite and soon-to-be-favourite streetwear brands have been making.

“Focus on age-appropriate cuts and start building a foundational wardrobe that’s based on staples that inherently have quite a bit more character than their boring, pedestrian equivalents. Stick to best-in-class brands such as Adsum, Aimé Leon Dore, Engineered Garments, Needles, Noah, Wacko Maria, and you’re guaranteed to find something that hits, regardless of where you fall on the spectrum. Finish with a garnish of loafers or a cosy classic such as Clarks Wallabees. Now you’re dressed for therapy.”

Thanks, Mr Schlossman. We like and subscribe.

If that stigma exists, we surely have fallen a long way from the great precedent set by, say, Messrs Billy Idol, David Bowie or Leigh Bowery. As our resident grooming guru, Mr Ashley Clarke, wrote last year, these days, it is customary for actors to wear makeup on the red carpet, President Emmanuel Macron is spending a pretty penny on keeping himself touched up and it is fairly expected that anyone – man, woman, child – going in front of a camera will have their hair and makeup done.

But for those of us who aren’t on YouTube or broadcast sports highlights, here are a few ways to weigh into the world of makeup, according to Mr Clarke. “A tinted moisturiser – a hydrating facial cream with a hint of colour to perfect the appearance of the skin – is a good starting point for the makeup neophyte,” he says. “Perricone MD makes an entirely undetectable one that you apply to your face after cleansing to give skin a healthful lift. An all-in-one product that looks like standard moisturising cream rather than foundation or concealer, it adapts to your skin tone to minimise pores, wrinkles and blotchiness.

“TOM FORD’s concealer is like a lip balm that you can dab on your eye bags or blemishes to make them disappear. Its eyebrow gel can tame your eyebrows and give them a cleaner, well-groomed look that will frame your face in a more flattering light.

“Ultimately,” Mr Clarke notes, “the difference for men today is that makeup is there if we want it – discreet or not – and the products are better than they’ve ever been. You can still wear your blemishes with pride and lug your eye bags around with you if you want, but you no longer have to.”

Indeed. A few years ago, we ran a story with the absolutely astonishing whirlwind of interests, talent and accomplishments that is Mr Ahmir “Questlove” Thompson, who is about 6ft 4in, just shy of 21 stone, and a man who has obviously put a lot of thought into looking good.

“I’m a big guy,” he told us. “You can’t just buy my clothes off the rack. A lot of my stuff will get re-tailored so it can accommodate me. I have my own T-shirt and hoodie company. I always felt that if I dressed more distinguished, that would add age to me. But [in my forties] I figured dressing like a 20-year-old in jeans and T-shirts 24/7 would age me even quicker. When I first started teaching, just as a joke, I got a few of those professor jackets with the elbow patches but, as I was looking in the mirror, I was like, oh, I kind of clean up nice. Maybe this could be a new thing for me.”

No surprise that, even back then, Mr Thompson had anticipated the more casual tailoring-paired-with-luxe-streetwear trend. And, recognising that darker colours, worn in monochrome outfits, are flattering on everyone, Mr Thompson says he went heavy into black clothes, “occasionally splashing a bit of colour, mainly because the accessories will pop out more. I concentrate on accessories,” he says. “I have more than 2,000 pairs of sneakers and 500 pairs of glasses that would rival Elton John’s collection.”

Yes.