Fashion

What does being a ‘well-dressed’ man in 2021 mean?

DJ, promoter, director, stylist, author, artist, documentarian, historian and man-about-town Chris Sullivan has been an integral part of London’s nightlife for more than 40 years. Having rubbed shoulders with the likes of Boy George, Steve Strange, Spandau Ballet and David Bowie, the dandy knows a thing or two about style. Here, he rallies his friends, including Jeremy Hackett and Martin Kemp, to question what it actually means to be well dressed in 2021
Image may contain Clothing Apparel Human Person Coat Overcoat Suit Footwear Shoe Sunglasses and Accessories
Edward Berthelot

It goes without saying that the parameters of what constitutes a “well-dressed man” have been somewhat muddied of late. The pandemic and ensuing lockdowns have forced us deeper into the realms of comfortwear than ever before and, in turn, away from the tailoring that once defined elevated masculine style.  

It begs the question, therefore, if whether, as we move out of lockdown, a suit, shirt and tie can still be held as the epitome of the ideal? And do such hitherto questionable combinations of bomber jackets with jeans or sneakers with sweatpants live up to the conceit or not?

Here, a gaggle of style mongers, fashion pundits, designers and pop stars – for whom dressing well has been a daily consideration for as long as they can recall – proffer their opinions.

Oliver Spencer, fashion designer
Victor VIRGILE

“The focus this year will be on getting out, meeting and dressing up, as, after the last year, there is no good reason not to get dressed up. Because the business uniform is totally antiquated, the suit will be deconstructed and very easy, very comfortable, more akin to pyjamas from very soft fabrics. Trousers will be cut a little higher with pleats for a roomier 1950s silhouette. The suit will be a more versatile animal, with polos, tees, etc. Once, the suit was the emblem of conformity; now it will be personalised in so many different ways that it is the opposite, because dressing up feels good.”

Robert Elms, BBC broadcaster
Andy Willsher

“For me, it’s correctly attired for the occasion. That may be old Levi’s and scuffed desert boots or it may be cool, Italian-cut, 1950s casual or Savile Row’s finest. It never means an ill-fitting suit that makes you look like an estate agent.”

Stacey Wood, founder and creative director of King & Tuckfield

“A well-dressed man today is a well-dressed man in two, five, ten years from today. He identifies with real brands in a not-so-real (fashion) world and invests in clothing and accessories that will stand the test of time in both shape and material. He seeks vestiary respect and not attention, as he knows it lasts longer.”

Jeremy Hackett, founder and creative director of Hackett
David M. Benett

“It’s about wearing clothes and not the clothes wearing you; not merely putting them on, being dressed and not dressed up. Clothes should become a part of you. And as many have been casual for a year, they will feel the need to dress up again and step out in style but still feel comfortable. So, well-polished, well-made shoes, a wider, more comfortable pleated trouser as a part of a well-fitted suit or matched with carefully cogitated classics.”

Tom Stubbs, stylist 
Kirstin Sinclair

“A well-dressed man today commands a repertoire of considered moves that combine favourite recent pieces with notions that he genuinely relates to, such as a vintage leather, a suit from his favourite tailor or a handsome timepiece, etc. He understands what works on him and understands what clothes actually mean and has thought about it.”

Martin Kemp, actor and former member of Spandau Ballet
Jim Dyson

“The boundaries have changed of late. I used to do TV interviews suited and booted, but now it feels out of place. But a well-dressed man, in my opinion, can be many things. When I put a great shirt underneath a sharp, well-cut suit, it feels special and I feel great, which is half the job.”

Nick Hart, fashion designer
Dave M. Benett

“A well-dressed man today means that his outfit is well considered even if there is a contradiction in that the look appears to be effortless or outrageous. It’s providing pleasure and even entertainment to the outside world/viewer that is ideally harmonious with the wearer’s given persona on that particular day.”

Bethany Williams, fashion designer
David M. Benett

“To me a well-dressed man is somebody who values craftsmanship and the artisans who craft our garments, [someone] who has an appreciation for sustainable materials and is not afraid to push boundaries and be playful with their style.”

Mark Powell, tailor
David M. Benett

“As most men have become, on the one hand, used to more casual dress, but, on the other, really feel the need to dress up again and get out, I think that the suit will play a big part but will be a softer coat with fuller trousers. It’s the opposite of the tight, short Thom Browne silhouette that’s been around for too long, has been adopted and abused and is really unflattering. Well dressed will mean confident, comfortable and not trying too hard.”

Tim Little, CEO and creative director of Grenson
Neil Mockford/BFC

“I always loved the quote ‘You only know that man is well dressed after you’ve been in his company for five minutes’. Well dressed, even though the style might change, means you have to have cared, as nobody is well dressed by accident. Your clothes should be made of quality materials that get better with time and the details are crucial. So, in 2021, you can be well dressed in a beautiful pair of soft, Italian calf leather sneakers and selvedge jeans of good quality, well looked after and not ruined with nasty jacket.”

Charlie Casely-Hayford, fashion designer
Kirstin Sinclair

“He is an aesthete. He appreciates and understands the nuances of aesthetics. He has an innate and sometimes subconscious understanding of balance, proportion, colour, silhouette, detail… and can even find a beauty in ugliness and the imperfect. Because he has an inherent sense of these pillars, he can stretch them in different directions to formulate his own style lexicon.”

Suggs, frontman of Madness
Rob Ball

“It has to be all about quality and classic items that might be tried and tested, like a John Smedley sweater or a pair of JM Weston loafers or instant classics such as an Oliver Spencer’s unlined jacket or a pair of Grenson thick-welted Archies. He looks as if he’s given his appearance some thought and has an idea behind what he’s got on his back. Also, those disposable days of clothing are over and now we’ve come out of this pandemic we’ll all be looking at things that will last, as opposed to here today gone tomorrow, as many people have been here today and gone tomorrow.”

Stephen Jones OBE, milliner
Jeff Spicer/BFC

“A well-dressed man has a certain ease or elegance, a certain comfort. And it doesn’t matter whether you’re wearing a football strip or white tie and tails, it’s the same thing.”

Joe Corré, founder of Agent Provocateur and owner of Jack Sheppard
David M. Benett

“To be well dressed in 2021, or at any time, you have to consider all the details of what you wear, understand the items’ quality and how they are made, then put these garments together by taking influence from who you think looks good, but give it your own original, personalised take. Some people think you can look well dressed in sportswear, but I think it should only be worn when exercising as, apart from that, I just do not get it.”

Christos Tolera, painter and dandy
David M. Benett

“A well-dressed man is like a well-dressed salad: you need to look at what’s on the plate first before chucking a load of dressing on it. There’s nothing worse than a short, portly man in a pair of tight drainpipes or a man with a big belly hanging over the top of his jeans. Wear them lower, higher or not at all. Don’t be scared of breaking the rules. There aren’t many, only according to your age and body shape. Finally, the hard and fast rule for summer is that a well-dressed man should never, ever wear flip-flops away from the beach.”

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