Ivy League Look: How to Wear It

Whether or not you are Ivy League at heart, the preppy-chic looks which have been so important for fashion not just in America, but all around the world, are likely to have had an influence on you. Smart-casual, words often used on party invitations and for after hours work meetings have their origins in preppy clothing; that marriage of the formal and the sporting look. Shining shoes with denim, blazers with casual trousers, training shoes in the same outfit as a necktie, preppy style is actually a daring clash, though due to its history and long list of designers and style icons inspired by its combinations, is considered conservative.

Forever New York and Long Island, the preppy aesthetic is very similar to the clubby, striped formality of academic and aristocratic England, which is hardly surprising considering the ethnic connection between the Waspish streets of the Big Apple and the old maritime nation. I feel particular warmth for preppy looks at this time of the year; when every child returns to school and fortunate freshmen enter university.

It feels out of place to be too modern at this time of year. From January onwards, the greys and blacks; the monochrome Dior Homme stylings work well, but from September until December, it’s time for stripes, cosy v-neck jumpers, burgundy loafers, club ties and classic denim.

Here are a few tips on how to wear it well:


The one thing I always remember at this time of year is the palette. Penguin looks just don’t fit when the golden tint of autumn is here. Wearing a red or green v-neck or crew neck jumper underneath a corduroy blazer will lift the outfit and give a sophomoric effervescence to an otherwise plain look. Though white is definitely the best shirt colour to use as a background for colours, pale blues and mid blues go strikingly well with reds and rich greens. Pink is a good colour to use also as it is a good companion to brown. Wearing a pink shirt with a brown crew neck jumper and polka dot navy blue bow-tie may sound like an eccentric look, but it is essentially classic as the colours act in harmony.


Denim is a great start to a preppy outfit. Choose classic, regular or slim fitted denim in mid and dark washes. Black denim is also good, and works well with virtually any footwear. Greys and very light washes look a little out of place with preppy looks, so avoid these.


I love wearing ties. I don’t have to wear them, but I do as I believe in their purpose as a splash of decoration and colour, finishing an outfit. After the heat of summer, it’s nice to squeeze a tie around my neck again. To perfect the preppy look avoid most modern ties; shiny pinks, purples and light blue checks are just wrong. Stripes, polka dots and woven plains are the essence of preppy neckwear. Ralph Lauren has a brilliant selection. However, if you are lucky, the best ties to buy are the original. Vintage ties are frequently available on auction websites such as eBay.


A pair of black and a pair of brown shoes are all a man needs for preppy footwear. If he is looking for something a little more casual, then he should try plimsolls or Keds. They suit preppy looks much more than branded trainers by Nike or Adidas, and are usually cheaper as well. In terms of shoes, choose classic styles like penny loafers (for that real straight-from-Harvard-yard look) or Oxford lace ups. Driving shoes are a little summery, but they make acceptable alternatives.