In a weird time loop befitting of his breakout movie, 2001’s Donnie Darko, Mr Jake Gyllenhaal is currently helming the new remake of Road House in the role originally filled by his Donnie Darko co-star, Mr Patrick Swayze. And while that might seem tangential in relation to the clothes Gyllenhaal is pictured wearing recently in New York, there’s a definite sense of him dressing for exactly where and when he is supposed to be, now aged 43. The hoodie and skeletal onesie of the high schooler (Gyllenhaal was actually 19 at the time) have evolved into a broad-shouldered double-breasted blazer and shirt, worn open to reveal a flash of jewellery. Stone-wash jeans in a similar tone to the shirt are elevated thanks to polished brown Derby shoes. Did an energy beam of intention lead him here and to this outfit? And is that the real secret to effortless dressing?

In recent years, rapper Kid Cudi has taken to flamboyant self-expression when dressing up, from wedding dresses (complete with veil) and floral gowns to bright-green hair. This look, then, is probably the equivalent of cosy sweats for him. But if the goal was to look relaxed while exuding a cool vibe, then he has achieved it with this black silky pyjamas-style ensemble, topped with a goes-with-everything camel trench coat. The only accessory needed? A pair of gold-framed sunglasses, even at night. That’s commitment.

All the pieces Mr Dan Levy is wearing here are basic staples, and yet he doesn’t look basic at all. And that’s thanks to proportions and styling. His jeans are the perfect fit – straight cut and ending right where his Sambas start. He’s done a French tuck (AKA a half tuck) on his T-shirt and added a belt, making him look more put together. His brown trench is relaxed but sophisticated, his beautifully tied jumper on his neck is oh-so-cool and effortless, and those round glasses in the style of Mr John Lennon add that whimsical flair that makes the look more interesting. His nonchalant look is giving Parisian chic in the best way.

Everyone needs an off-duty outfit. Even Mr Harry Styles, whose exuberant looks are often adorned with sequins, ruffles and the occasional feathered boa, has his own version of easy-going attire. Still, when he does swap the stage for the New York City sidewalk, he cuts a stylish figure. The singer stepped out in a casual early spring outfit, consisting of a white T-shirt, fuzzy coffee-brown cardigan, beige corduroy trousers and adidas Sambas. If there’s one key takeaway to glean, it’s that we should all be carrying an emergency pair of loafers with us – you never know when a quick change is needed.

He may not have been in the spotlight for long, but Mr Archie Madekwe – the 29-year-old British actor who played Felix’s wickedly stuck-up cousin Farleigh in Saltburn – is already high up our style ranks. This intentionally simple outfit shows that he knows how to make the smart-casual dress code work, and how to make it work for him. We could talk about the heritage workwear influences of the jeans, or the retro sportswear inspiration of the otherwise refined, buttery suede Louis Vuitton jacket. But the sporty socks and polished formal loafers are what this is all about – take note.

Modern artist and man about town, Mr Alex Israel lives one of those ultra-chic yet mostly under-the-radar lives that is truly aspirational (if his Instagram is anything to be believed, that is). Also aspirational? This low-key luxe tonal outfit worn to an event in Beverly Hills is proof positive that jeans and a sweater don’t have to be boring. Indeed, there are other options than simple pullovers – we love this collared cardigan. A simple shell parka and sunglasses indoors finish off the look.