Editors Pick Style

Dress for Ivy League Success With These 17 Preppy Essentials

The Sport Coat

The terms ‘blazer’ and ‘sport coat’ are often used interchangeably, but any prep worth his salt knows that this is sacrilege of the highest order. While both are designed to be worn with non-coordinating trousers such as jeans or chinos, a blazer is a solid colour (often navy and fitted with gold buttons in a nod to its nautical origins) whereas a sport coat or sport jacket is cut from a jazzier patterned fabric and finished with more casual details like patch pockets and elbow patches. Sport coats are often a little more relaxed in cut, so perfect for layering now the colder weather has arrived.

Camoshita for Trunk Double Breasted Jacket, £1,295

Camoshita X Trunk jacket

Some menswear fans hold that the Japanese actually do Americana better than the Americans – and this sport coat, created by prep-obsessed Japanese tailoring house Camoshita for the tenth anniversary of Chiltern Street destination store Trunk appears to prove their point.

Available at Trunk Clothiers.

Anglo-Italian Sport Jacket, £990

Anglo Italian jacket

Crafted from Glen Plaid material in supremely versatile shades of autumnal brown, the added advantage of the Anglo-Italian’s take on this tailoring classic is that it’s half-lined meaning you won’t be creating your own personal sauna when you slip it on over a cashmere roll-neck.

Available at Anglo Italian.

Jack Classic Jacket, £650

DAKS jacket

DAKS was founded back in 1894, and its signature brown, black and cream check has become an instantly recognisable symbol of the tailoring house since it was introduced in 1976 – and with the current seventies menswear revival, it feels just as fresh as it did 44 years ago.

Available at DAKS.

Brooks Brothers Red Fleece Gingham Sport Coat, £360

Brooks Brothers Two-Button Gingham Sport Coat

For a trimmer take on an item that’s often cut with an intentionally slouchier silhouette, take a look at this slim-lapelled sport coat from Brooks Brothers’ younger Red Fleece line.

Available at Brooks Brothers.

The Sweatshirt

JFK. Paul Newman. Edward, Duke of Windsor. All preppy style icons. All loved a sporty sweatshirt. Today, these remain a staple of any self-respecting prep’s armoury, either in a classic grey melange or with something a bit more graphic that pledges your loyalty to your alma mater, your sports team, hell, even the brands you love. And while we love a classic, here are a few remixes of the wear-anywhere wardrobe staple.

Champion X Todd Snyder Heavyweight Turtleneck Sweatshirt, £92

Champion X Todd Snyder jumper

Sometimes the tiniest twist creates something we never knew we needed. Case in point, this crazily cosy funnel-necked, fleece-line grey sweatshirt from the new season Champion and Todd Snyder collaboration.

Available at Todd Snyder.

Gant Crew Neck Sweatshirt, £125

GANT jumper

If you’re not into sports, commit your chest to your love of the countryside instead with this oversized sweatshirt, a part of the new collaboration between Ivy League-inspired Swedish label Gant and notoriously well-dressed British artist Luke Edward Hall.

Available at Gant.

Polo Ralph Lauren Duffel Bear Fleece Sweatshirt, £155

Ralph Lauren jumper

Originally introduced in 1991, retired in 2001 and reintroduced in 2013, Ralph Lauren’s bear (he doesn’t have a name) has become a near cult-like figure in the menswear world. Whether dressed in a Purple Label tux or the label’s recent collab with Palace skateboards, he’s now mostly found on the American designer’s sweatshirts, dressed in suitably preppy garb – and this season, wearing his plaid duffle jacket and velvet slippers, is no exception.

Available at Ralph Lauren.

John Smedley Marcus Classic Crew Neck, £180

John Smedley jumper

If you want to keep the laid-back vibe of a sweatshirt, but want something a little more on-the-clock-friendly, go for a crew-neck in a fine-gauge knit. This from John Smedley, woven from luxurious Merino wool, is the definition of effortlessly stylish.

Available at John Smedly.

The Rugby Shirt

As a way of dressing born out of the most gentrified school campuses of the East Coast, it’s no surprise that many of the items that define the genre today come from the rarefied sports that tended to be played there: rowing, golf, sailing and rugby. That’s why, despite rugby not being a particularly notable part of the American sports landscape nationally, the rugby shirt has still become an integral part of a prep fan’s wardrobe.

Drakes Green and Pink Stripe Cotton Rugby Shirt, £195

Drakes Green and Pink Stripe Cotton Rugby ShirtOne look at the new season shirts from Drakes and it’s fairly safe to say that if this Savile Row tailoring house had a rugby team, I reckon it would have the best kit in the country.

Available at Drakes.

Marks & Spencer Striped Long Sleeve Rugby Top, £29.50

Marks & Spencer rugby shirt

Bold stripes on burgundy for the win.

Available at Marks & Spencer.

Rowing Blazers Constellation Rugby Shirt, £180

Rowing Blazers rugby shirt

While we call it The Plough over here in the UK, across the pond the constellation Ursa Major goes by the frankly far-more-fun name of the Big Dipper. Whichever you prefer, it’s hard to deny that it makes an eye-catching graphic for this appropriately midnight blue rugby shirt.

Available at Rowing Blazers.

Berg & Berg Rugby Sweater Navy, £207

Berg & Berg rugby shirt

Cut to a slim silhouette from 100 per cent cotton and trimmed with a contrast chambray collar, this is the sort of rugby shirt that’s made to be worn slightly smarter – tucked into a pair of chinos or even slipped on under a cord suit.

Available at Berg & Berg.

The Winterproof Loafer

Whether penny, tasselled or kiltie, loafers are the ultimate transitional shoe for an Ivy Leaguer – worn casually with a white sports sock or more smartly with hosiery that coordinates with your trousers. However, as we verge into the definitively wet seasons, you need a slip-on that will prevent you from slipping over. Look out for chunky soles with rubber grips and deep treads to make sure an unexpected downpour doesn’t lead to you falling down.

Edward Green Duke Penny Loafers, £995

Edward Green loafer

If a stockier sole isn’t your vibe, there are still plenty of more traditional silhouettes out there that have evolved to deal with precipitation. These superb Duke penny loafers from Northampton’s Edward Green, with an elegant low profile, have swapped the usual leather sole for a rain-beating rubber one.

Available at Edward Green.

Church’s Tennant Bookbinder Fumè Leather Tasselled Loafers, £460

Church’s loafer

Artfully treading the line between classic and contemporary, these kiltie loafers from Church’s combine the detailing of a Scottish classic with beautifully brawny, Goodyear-welted soles.

Available at Mr Porter.

Herring Kramer Mod Rubber-Soled Loafers, £135

Herring loafer

British shoemaker Herring has also chosen to pump up the volume on its loafers. This superb mock-croc leather loafer, jacked up on suitably sturdy soles, will look great with a pair of straight cut chinos and a slouchy sweater.

Available at Herring Shoes.

Blackstock & Weber The Ellis Penny Loafer, £230

Blackstock & Weber loafer

Shoes featuring contrasting black and white (or brown and white) leathers hit peak popularity during the Jazz Age in America, and have enjoyed a modest renaissance worldwide with menswear fans since Ryan Gosling wore a pair in La La Land (2016). New York shoemaker Blackstock & Weber makes some of the best I’ve seen, featuring a more modern, thicker sole and swapping the more traditional shiny leather for a beautiful matt pebble grain.

Available at Blackstock and Weber.

SevenFriday Mr. President Opticals, £208

SevenFriday opticals

With many of our meetings shifting to Zoom for the foreseeable future, your glasses are one of the few ways to express any sort of personal style when all anyone else can see of you is from the neck up. Want to catch the attention of your superiors while working from home? These bold, thick, faux-tortoise shell opticals from German label SevenFriday, inspired by politicians of the 1970s, are true boss-level frames.

Available at SevenFriday.

About the author

Nick Carvell

Nick Carvell

A lifelong fan of double denim (even triple on occasion), Nick started his career as Social Media Editor of mrporter.com before working as Associate Style Editor at British GQ then Editor of The Jackal. He is now a freelance menswear editor – as well as Oracle Time’s Style Editor-at-Large – writing from lockdown at his kitchen table in South London.

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