Buy a navy collared knit, something sleeveless to go over it, and a pair of stone or khaki trousers. About $150 for the three, and they work with the jeans and plain tees already in your wardrobe.

Then, in this order: a second collared knit in stripes, a light blue oxford shirt, brown shoes, and last of all the navy jacket.

What Decides the Order

The garments are settled and have been for decades. Navy jacket, oxford button-down, khaki chinos, penny loafers, a knitted collar, something sleeveless in wool.

Sequence is the open question, and the one used here is how many other purchases an item needs before it does anything. A collared knit needs none. A sleeveless layer needs one thing underneath. A jacket needs a shirt, trousers and shoes at roughly its own level of formality, three purchases deep before the first one earns its price.

The second reason is in the shops. Brooks Brothers has reported double-digit growth in tailored apparel, opened a 10,000 square foot flagship at 195 Broadway in New York, and started a University Shop line aimed at buyers in their twenties. Prada, Miu Miu and Chanel have shown the codes. Jonathan Anderson at Dior and Michael Rider at Celine, both new in post, put prep references into their first collections. What all of them put on the runway is the loosened version: shirting worn out, knitted layers, flat shoes, trousers with room in them.

The tailoring is the part this revival has left alone.

Check What You Already Own First

Some of this is already in your wardrobe, and buying it twice is the usual way a first order gets wasted.

Plain white leather trainers. The loosened version is worn on flat shoes at least as often as on loafers. Owning a clean pair moves shoes to the back of the order, behind the shirt.

Dark straight-leg jeans. A collared knit over dark denim is a finished outfit.

A plain crew sweater in navy, grey or cream. Does most of what step two does. A sleeveless version handles warm weather better.

A plain white or grey t-shirt with no print. Goes under a sweater vest without the neckline showing.

A canvas tote. Already part of this wardrobe, and rarely worth buying new.

Some of it does not carry over. Black trousers, since the palette runs warm and navy and stone or tan gives everything above it more to work with. And slim-fit dress shirts, cut with no room to layer knitwear over.

Settle the Colour Before You Choose the Garment

Deciding this first is what stops the second and third purchase clashing with the first.

Navy for the first item. It sits above every trouser colour worth owning and hides wear better than the alternatives. It registers as this style with no pattern involved. White reads as sport, a narrower thing. Bottle green and burgundy belong here as third or fourth purchases.

Cream, oatmeal or mid grey for the layer over it. The point of that layer is contrast against the navy, and cream is the shade that reads this way and no other way.

Stone, khaki or tan for the trousers. Navy, cream, white and grey all sit above a warm neutral without competing with it.

Something striped for the fourth item. Two plain colours are already in the wardrobe by then, and a stripe containing one of them works with both. It adds two arrangements where a third plain colour would add two identical ones. A stripe in two new colours starts a third palette.

For the shirt, white is right if it has to cover smart occasions. Light blue is the better first one for a wardrobe that is mostly casual. It hides collar wear and goes under knitwear without the hard edge white gives.

Six colours cover it: navy, cream, stone, white, grey, and one saturated accent used on its own against the rest.

The Collared Knit

René Lacoste had a shirt made for the 1926 US championship with the back hem cut longer than the front, to keep it tucked when he reached up to serve, and a collar knitted stiff enough to turn up against the sun on the back of his neck. Both survive on a well-made polo, and both are quick to check.

Lay the shirt flat and compare the hems. Level hems mean it was cut as a tee with a collar added. Then hold it up by the shoulders. A collar knitted with its own structure stands up on the hanger and holds that shape through the wash, where one cut from the same jersey as the body will start rippling at the edge after a few months.

Buy it in navy. Sizing is forgiving here in a way it is not on a woven shirt. A polo cut too big reads as a decision, and erring large costs less than erring small.

Piqué polos start around 165 GSM, sit around 250 in the middle of the range, and run to 300 and above at the heavy end, with most product pages publishing the number. Below about 165 there is not enough cloth to hold a collar up. Shoulder seam at or just past the shoulder point, sleeve ending around mid-bicep.

A rugby shirt is the heavier version of the same garment and carries a couple of details out of the game. The buttons are rubber, soft enough to be safe in a collapsing scrum. The collar is woven twill, usually white, which holds its shape in a sport where opponents take hold of it. Both are worth finding, and the version that has them costs a few dollars more.

The fourth purchase is a second one of these in stripes. Nothing more to it than that.

The Sleeveless Layer

A sweater vest or a cardigan in cream, oatmeal or grey, worn over the knit you just bought. The collar and cuffs underneath stay visible, the colour and texture change, and no second base layer was needed to get there.

Everything else depends on the yarn. Shetland has short springy fibres and a slightly hairy surface that holds a soft halo when it is knitted loosely. Merino is finer, smoother, and drapes flat. Both are wool. The smooth fine-gauge version looks like office knitwear, and over a collar you want the other one.

Knitwear weight is rarely published. Ask. A vest with enough weight in it sits cleanly over a collar and hides the shirt's texture underneath. Armhole close without cutting, hem at the waistband or just below, enough room across the chest that the shoulder seam does not drag outward when there is a collar underneath.

The Trousers

Khaki is a colour and chino is a cut, and the two get used as though they were one word. Khaki comes from the Persian and Urdu for dust-coloured and entered military use in India in the 1840s. Chino is a trouser made from cotton twill, and Merriam-Webster dates the first English use to 1943 with the origin listed as unknown. Chinos come in navy. Khaki-coloured trousers are frequently not chinos.

Buy it at around 240 GSM, the weight that works most of the year. 170 is summer cloth, anything past 340 is winter. Cut is relaxed, at or near the natural waist, straight leg, little or no break at the shoe.

Hold it to a window: twill heavy enough to hold a crease is opaque, and its diagonal rib is easy to see. Away from the cloth, look at the pocket bags. Proper cotton outlasts the trouser and thin gauze splits first, and a plain flat waistband is what you want at this price.

The Oxford Shirt

One word on the label decides what the collar will do, and that word is non-iron. Its cousins are wrinkle-free and easy care.

Those finishes soak the cotton in a crosslinking resin, usually DMDHEU, then cure it with heat so the cellulose chains bond to each other and cannot move into a crease. The chemistry dates to the 1950s and it works.

The trade is real and it is measurable. US Patent 4,090,844, setting out the state of durable-press finishing, puts tear strength down by around half, breaking strength down by 50 to 60 per cent, and abrasion resistance down by 75 to 85 per cent. Optimised runs from the late 1970s got the loss to 11 and 14 per cent with particular catalysts, reported in the literature as unusually good. Citric acid holds 80 to 90 per cent of the strength and BTCA around 95, both in exchange for less crease recovery.

US Patent 4,483,689 says where that shows up on a worn shirt: a few machine washes bring frayed edges at the cuffs and collar, and worn pale lines along the creases. The collar and the cuffs are the parts that show.

Stiffness is the other half of it. An oxford button-down is meant to arc up between the collar button and the top shirt button, and that arc wants a soft collar with enough length to have somewhere to go. A must-iron shirt has one. No US agency requires the treatment on the label, so the word non-iron is the whole of the disclosure.

Fusing and length reach the same collar. Most shirts have an interfacing glued on with heat, some have an interlining stitched in that floats loose, a few have nothing at all: pinch the collar between finger and thumb and rub the two faces against each other, and a floating layer slides where a glued one behaves like a single board. Then there is length, with points around three and three-eighths of an inch leaving enough for the arc. Men's Wear of February 1926, measuring a size 15.5 Brooks Brothers button-down, recorded points of three and a half inches with the buttons three-quarters of an inch from the tips and three and a quarter inches apart.

Oxford cloth itself is a basketweave, coarser and heavier than the poplin used for business shirts. Shirting runs roughly 100 to 200 GSM, or three and a half to seven ounces per square yard, and oxford sits at the upper end.

Some qualifications. Collars with a light interlining hold their shape better than collars with nothing in them at all, and fused collars are the quickest of the three to iron. Among people who collect 1950s and 1960s shirts there is a standing argument that the whole business is overstated, that the originals had small collars barely arcing at all, and that softness of cloth is what actually made them good. That may well be right. The label is the part I would still hold to.

Buy light blue before white, and get the shoulder seam on the shoulder point with room to layer knitwear over it.

Shoes

Blake stitching runs through the insole and outsole, and a shoe built that way comes apart for resoling somewhere around year three. Cemented soles are glued on and get replaced whole. Establish which of the two you are looking at before anything about the shape.

The strip across the vamp of a loafer with a cut-out in it is where the name came from. Students kept a dime in the slot, a dime being the price of a call from a payphone and the slot being the one place to keep emergency money without a pocket. Pennies took over later, partly because copper looked better against brown leather. The rolled bundles of leather where the strap meets the body are called beefrolls and should be stitched into the upper.

On a deck shoe, push a thumbnail into the tread. The grip comes from thin slits cut across the rubber, a process called siping, patented by John F. Sipe in 1923 as US 1,452,099. A siped sole opens under the nail.

Brown leather, loafers or something flat, or clean white leather trainers if you do not own a pair. Buy them snug. Leather slip-ons stretch across the width, and a pair that already feels comfortable in the shop will be loose at the heel by the end of the season.

The Jacket

Navy, soft-shouldered, $200 up.

The case runs like this. A soft navy jacket converts clothes you already own. Over dark denim it reads one way, over grey trousers another, over chinos a third. One purchase, three outfits, no supporting cast. Add brown penny loafers and the claim is that two items make a complete start.

For a particular reader that is right. If you already own trousers you like, know your jacket size, and have somewhere to get the sleeves shortened, buy the jacket and skip the rest of this.

For the person typing what to buy first it is the wrong purchase, for reasons that are about money and fit rather than taste. That plan runs six to eight hundred dollars against $150 for steps one to three here. The shoulder seam either sits on your shoulder or it does not, and no tailor can move it cheaply. On every other item here a fit error can be styled around. And the version being worn now leans on tailoring least.

When you do buy one, the traditional cut is undarted through the front, soft shoulder, no padding, hanging straight down from the chest. Three buttons with the lapel rolling over the top one. Hopsack and fresco are open weaves that hold their shape without lining. Get the shoulder right in the shop and budget for shortening the sleeves.

Complete Looks and What Each One Needs

On page 59 of Take Ivy, the photobook that recorded eight American campuses over the spring of 1965, a Princeton student crosses the quad in olive shorts, penny loafers with no socks, and an oxford button-down with the sleeves down. The sleeves are the part worth copying. It is warm enough for shorts and he has not rolled them. That accounts for most of the difference between the photograph and a summer outfit. Purchases five and six.

The layering move is older than most of what gets called preppy now. Writing about the 1970s, Alison Lurie recorded polo shirts and jersey turtlenecks worn underneath oxford button-downs, with a sweater draped around the neck and never put on. Two collars, the knitted one sitting outside the woven one. It came back at New York Fashion Week last season under the name double polo collars. Purchases one and five, plus a sweater you already own.

Then there is the one with a proper name. The broken suit is a navy jacket over khaki chinos with a button-down and loafers, and a tie when the day calls for it. It is what teaching staff wore, and Southern campuses still turn out in it on game day. Every purchase in the order, and it sits at the end of the order for that reason.

One garment tells you which school you are in. A polo worn with loud patterned trousers is prep. The same polo under a cricket sweater with eggshell linen trousers is Ivy. A cricket sweater is a cable-knit V-neck with a stripe tipping the neck and the cuffs, and it is the piece that carries more of that look than anything else in it.

After three purchases you have the version people are actually wearing this year: collared knit, sleeveless layer over it, stone trousers, flat shoes, nothing tucked and no tie. Add the striped knit at purchase four and the same four pieces give you a second outfit that reads differently at ten paces.

What to Leave Until Later

The items that read hardest as this style each work in about one outfit, which is what puts them after the seven above.

Madras, seersucker and bright patterned trousers are single-outfit garments. Boat shoes are summer wear and read as summer wear. Ties are an accent here, and a knitted one is the version that still reads current. Anything with a crest, a signet, a ribbon belt or a nautical motif belongs to a wardrobe that already exists.

Argyle deserves a longer note. It tends to get bought earlier than it earns its place. The pattern came out of the tartan of Clan Campbell in Argyll, on the west coast of Scotland, and Highland knitters were working the diamonds into kilt hose by the seventeenth and eighteenth centuries. Pringle of Scotland, by its own account, commercialised it at Hawick by turning the knitting machine patterns ninety degrees. The golf link arrived later and arrived through one person: Edward, Prince of Wales, wearing argyle socks and sleeveless argyle knits on the course through the 1920s and 1930s while being close to the most photographed man alive.

What to look at when you buy one: the thin diagonal lines running across the diamonds. That is the overcheck, and printed imitations usually leave it out.

How Many of Each to Own

Eleven items in total. Most people who wear this convincingly own four or five pieces of it and left the rest of their wardrobe alone.

What Each Budget Buys

$150. Navy collared knit, sleeveless layer, stone trousers.

$350. The three above, plus a striped collared knit and a light blue oxford shirt. Covers a weekend through to a smart-casual office.

$700. The five above, plus brown shoes and a second pair of trousers, with about $150 held back. Six weeks of wearing the first five tells you what the seventh should be.

Above $700. The jacket, and only the jacket. Put the whole remainder into one and spend the time on fitting it.

When in the Year to Buy What

Buying order and calendar order are not the same thing.

Knitwear is cheapest in late summer and best stocked in early autumn. Buy a sleeveless layer in October and you pay full price for the item the whole shop is queuing for. Cotton trousers and collared knits are widest in spring, and the order here falls out along the same calendar: steps one to three in spring, four and five in late summer, shoes in autumn when the leather ranges refresh.

Jackets are the exception. Buy one whenever you find one that fits in the shoulder, in whatever month that happens.

Which Step to Start At

From streetwear. You own the trousers and the trainers. Buy the collared knit and the sleeveless layer and nothing else. Two purchases against a wardrobe of graphic tees and relaxed bottoms produce the loosened version, and the oxford shirt can wait a year.

From smart casual for work. You own shirts and trousers. Your gap is the knitted layer and the shoes. Start at step two, then jump to step six.

From nothing. Steps one to three in order, with the shirt fifth however much more it looks like the pictures.

From a wardrobe of black. Trousers first, in stone. One pair of warm-coloured trousers converts more of what you own than any top half will.

Common Questions