Not only is size not a barrier, sometimes it is an asset. Some of the men who inspire me the most have larger builds. They wear things such as Filson-styled mackinaws and brimmed Stetson hats in ways that I wish I could.

Mr David DeMarte is an American high-school art teacher with a side gig handcrafting leather watch straps through his label David Lane Design. He is a barrel-chested man who has to dress for two work environments. In the classroom, he wears soft-shouldered hopsack sports jackets with grey woollen flannel or tan cavalry twill trousers. In his workshop, he wears chambray work shirts, chunky RRL shawl-collar cardigans and raw denim jeans. His combination of tailoring and workwear allows him to mix and match (the same chambray work shirts can be used to dress down tweed sports jackets and corduroy suits). And the workwear side of his wardrobe looks more authentic on him because of his burly physique.

“I’ve been really into RRL for a while,” DeMarte says. “But only about 20 per cent of what they make fits me. It sucks because I live in a town with not many high-end clothing stores, so I have to order everything online.”

One way to reduce return rates, he says, is to measure clothes you already own. Start by laying a garment flat and measuring it from armpit to armpit at the front, shoulder seam to shoulder seam at the back, and the bottom of the back collar seam to the hem to get the length. Then keep those measurements on file. “This way, when a store posts measurements of their garments online, you can get a sense of whether they will fit,” he says.

Vintage is another area where larger guys often have more luck. Mr Tony Sylvester is a British singer who runs the independent menswear label AWMS. He has cultivated a dedicated following by replicating iconic items from the golden age of men’s style, such as the astronaut Mr Neil Armstrong’s resplendent red panelled cap and the artist Mr David Hockney’s short-sleeved grey sweatshirt with the word DAFT cheekily emblazoned across the chest.

“Looking back, I think I got into heritage menswear out of practicality,” Sylvester says. “Brands such as Barbour, Filson, LL Bean, Carhartt and Pendleton always carried larger sizes in their catalogues, so it was easier to find things that fitted, especially in vintage shops.”

As an inveterate thrifter, Sylvester estimates that about three-quarters of his wardrobe comprises second-hand items. He has a Pendleton Topsider jacket in Black Watch tartan, a pair of 1960s senior cords (in the style of BODE), a stout Champion reverse-weave hoodie that he has owned for more than 30 years and a Royal Navy-issue pusser’s grip holdall he inherited from his father. In winter, he layers his heavy Melton naval duffle coat over his suits. By combining old with new, he creates outfits that are just off-kilter enough to keep things interesting.

For men yet to dip their toes into vintage, Sylvester recommends starting with a military surplus jacket, such as a jungle jacket or an M65. “This is something you can wear with a polo shirt, chunky turtleneck or even an Oxford button-down shirt with a tie,” he says.

Ever since anti-authoritarian youths turned the army jacket into a counter-cultural pose, the military surplus jacket, particularly in the drab olive colour known as OG-107, has stood for more than warfare. “It has so many layers of cultural meaning now that no one assumes you’re a soldier just because you’re wearing one,” he says. “People are more likely to think you’re wearing it for counter-cultural reasons than the original purpose it was built for.”

Regardless of body type, nearly every off-the-rack purchase will benefit from a trip to the tailor. Knowing the particularities of your body type can help you achieve a better fit or silhouette for only a small extra cost. Sylvester notes that most ready-made garments have little seam allowance, so they can’t be easily let out (except for high-end trousers, where some extra material may be in the waistband). Instead, he says, it is better to err on the slightly larger side and have things taken in.

DeMarte adds that larger guys will often find themselves wrestling with overly long sleeves. You can always shorten sleeves from the cuff end, but consider preserving the placket so you can comfortably roll up the cuffs.

More formal items, such as suits and sports jackets, can be trickier. It is often not a big deal if casual clothing doesn’t fit perfectly. Sometimes an idiosyncratic fit is part of the charm, but no one looks good in a suit that’s puckering or pulling. DeMarte and Sylvester say they have had much better experiences going custom, whether made-to-measure or bespoke.

Mr Ethan Newton is the proprietor of Bryceland’s & Co, a high-end men’s store with branches in Tokyo, Hong Kong and London. As someone who has been present at many bespoke fittings, he has strong views on how to dress a larger physique. “It’s less about size and more about proportions,” he says. “A guy can be larger or smaller, but some guys have a natural V-shaped figure and some don’t.”

For men who don’t have much of a drop between their chest and waist measurements, Newton likes to fit them in a jacket with a generous upper body. By extending the shoulder line and creating a fuller chest, a tailor can more easily create that traditionally masculine V-shape.

“I also like jackets to have wider lapels, fuller sleeves and hips that hug the body,” Newton says. “The trousers should also sit higher on the waist and have a little more ease through the thigh. I always give the analogy of a bell. You don’t want your upper torso to look like a bell and then have these skinny trousers flapping underneath it. The trousers should be cut so the jacket and trousers look cohesive, and the legs should be full enough to not catch on your calves mid-stride.”

I realise that much of this advice can be applied to anyone and that insecurities around dressing larger figures are not unique. Dressing is such a personal act. Clothing sits on our skin and is the primary visual method by which we present ourselves to the world. When larger men tell me they don’t think they can wear something, I hear that they don’t want to be perceived – an anxiety that lives in many of us, regardless of body type.

There is such joy in moving through the world in clothes that make you feel good, perhaps even powerful or foolish, rather than invisible and anonymous. Getting to this place is more about a mental journey than just finding clothes that fit. “Jackie Gleason is one of the best-dressed men of all time, particularly in his role in the 1961 film The Hustler,” Newton says. “Bigger doesn’t have to be bad. It can mean you’re masculine, powerful and generous in your proportions. Guys should stop thinking, ‘I’m overweight, so I can’t look good.’ They should think, ‘Yeah, I’m a bigger guy, so certain things will look so much better on me than anyone else.’ Embrace who you are and dress for the body you have, instead of the body that society or some fashion designer thinks you should have.”