In 1965 a Japanese publisher put out Take Ivy, a small photo book of American college students walking to class in oxford shirts, chinos and beat-up loafers. Teruyoshi Hayashida took the pictures, and for 45 years the book existed only in Japanese, until powerHouse Books printed the first English edition in 2010. I bring it up because it keeps coming back. Vogue reported this year that Jack Carlson built his second J.Press collection straight off its pages, and GQ's autumn sweater guide credits a resurgence of American prep for the collegiate knits showing up everywhere. Heritage dressing is having a moment because it is the opposite of a moment. These clothes were made to be worn into the ground, and that is the appeal. Start with the outer layer. Barbour has been at this since 1894, when John Barbour began selling oilskins to sailors in South Shields, and the Beaufort is still made by hand at the Simonside factory there. Next to it, the Polo Ralph Lauren Prince of Wales check coat does the city version of the same idea. My rule is one heritage layer per outfit, so the wax jacket goes over a plain navy crewneck, not a tweed waistcoat and a flat cap. What I would skip is the Purdey tweed gilet if you live somewhere warm, because it is a cold-morning piece and it looks like a costume in seventy degrees.

A checked flannel is the most honest shirt in menswear. Nobody wears one to impress anyone, which is exactly why it reads as confident. Portuguese Flannel is the label I would look at first: a four-generation family business with mills around Guimarães, and a brand that says plainly it does not follow trends. The brown Stalia check is the shirt you will reach for every Saturday until spring. For something drier, Hartford has been making shirts since Yves Chareton started it in 1979 with old stocks of oxford and chambray, and the ivory Paul flannel is the shirt that built its reputation. The OrSlow western denim shirt comes from Ichiro Nakatsu, who runs the label out of Nishinomiya and reworks vintage American workwear with a collector's eye. Wear any of these open over a white tee with the sleeves rolled twice. What I would skip is the JW Anderson reversible-collar check if you want a shirt that disappears into an outfit, because that collar is the whole point of it and it will always be the first thing people see.

Take Ivy is mostly a book about trousers, if you look closely. The students wear chinos that stop just above the shoe, a touch too short, and that proportion is what makes the whole look work. De Bonne Facture, which Déborah Neuberg founded in 2011 to keep traditional French know-how alive, does a pleated puppytooth wool-flannel in green with exactly that easy, slightly rumpled drape. The Polo Ralph Lauren corduroy is the safe brown you already know you need, and the ecru wool-twill pleat from Portuguese Flannel is the one to wear with a navy blazer when chinos feel too casual. For denim, keep it straight and mid-blue. The Dries Van Noten Peyter jean is cut clean enough to wear with a loafer. My test for a heritage trouser is simple: sit down in it. If the hem lifts to show a sliver of sock, you have the right length. What I would skip is the Acne Studios stain-print jean for this look, because the print fights with checks and tweed, and heritage dressing only works when one thing is loud at a time.

Shoes are where heritage dressing either lands or looks like fancy dress, and the trick is wear. Diemme was founded in 1992 by the brothers Dennis and Maico Signor in Montebelluna, the Veneto town known for mountain and ski boots, and the Cornaro suede hiker carries that technical history without looking like you are about to climb something. George Cleverley has been on Cork Street since 1958, and the Bradley II suede loafer is how a Mayfair shoemaker reads the campus penny. Then there is the Sebago Ranger, from a company founded in Maine in 1946 whose Docksides became a college uniform in the 1980s. If you only buy one pair, make it a brown suede loafer, because it works with corduroy, flannel and jeans equally. What I would skip is the black Timberland six-inch if your wardrobe is all brown and olive. It is a great boot, but black reads city and the rest of this edit reads country.

The accessories in a heritage wardrobe should look like they came from somewhere specific. Johnstons of Elgin has been working in the north of Scotland since 1797 and became the first Scottish company to weave cashmere in 1851, and the Hirta check scarf is the softest way into tartan I know. Begg x Co traces its roots to 1866 in Paisley and still raises its Arran scarves with natural teasels, which is why the surface has that faint ripple. For belts, Anderson's in Parma makes only belts and named itself after the Savile Row tailor Anderson and Sheppard, which tells you everything about its taste. A brown full-grain belt is the one thing every outfit above needs. The RRL striped denim tote is my pick of the bags. Ralph Lauren launched RRL in 1993 and named it after the Double RL Ranch in Colorado, and the tote has that faded ranch look built in. What I would skip is the cap if you are already wearing tweed, because the two together tip straight into costume.

What I like about heritage menswear is that it asks nothing of you. It does not need a new silhouette every season or a reason to exist. The Take Ivy students were not trying to start anything; they were dressing for cold walks across campus, and sixty years later we are still copying them. If you are building this look from scratch, go in this order: the wax jacket, a brown flannel shirt, one pair of pleated trousers, the suede loafer and a scarf. That is a full outfit and it covers most of autumn. Add a second shirt and the boots when the weather turns. Then let everything get a little worn. The wax jacket gets better with every crease and the corduroy softens with every wash, and that is the whole idea. Heritage clothes are supposed to look like you have owned them for years, even if they arrived last week.

Heritage clothes get good by being worn, so this last rack is for the pieces I would break in on purpose. Four checked flannel shirts lead it, from Acne Studios, Portuguese Flannel, SECOND / LAYER and Nili Lotan, and any of them works under the Barbour checked corduroy-trimmed waxed-cotton jacket. Slowear Incotex makes wool-blend flannel trousers and Drake's makes straight-leg twill, so the bottom half is covered. For shoes, the Sebago Koala suede desert boots and Dan penny loafers do the daily work, with the VINNY's Moto suede boots as the sharper pair. What I would skip: the NN07 checked weekend bag on a day that already has plenty of checks.

For more in the same spirit, take a look at Cashmere Menswear and Trending Menswear.