Period Piece: The Ivy Look

ivy style 1 Period Piece: The Ivy Look

The Ivy League look is one of those truly timeless looks. Though the golden age of the 1960s is over, the appeal of the Kennedys, the Amory Blaines, and the Paul Newmans of the world is eternal.

So tuck that shirt, roll up those khakis, and slip into some old penny loafers – EveryGuyed is here to help you with that Ivy look!

The rules, tips, nuances and details of the look are byzantine and occasionally confusing, so here are just a few small tips to get you started.

The Button Down Shirt

A staple of the look, the button-down shirt is one of the most quintessential American pieces of clothing. Worn by icons such as Anthony Perkins and Paul Newman, there’s nothing as all-American as the button down shirt.

First made by Brooks Brothers, the button down shirt is now available from a variety of retailers, at a variety of costs, in a variety of colors, patterns, and materials. Here are just a few things to consider when you pick yours.

  • Material comes first. The best button down shirts are made of oxford cloth, and are 100% cotton. The oxford makes for a fine finish, and the cotton lets your skin breathe.
  • Color and pattern are largely unimportant, but be sure you at least have one in white, and one in blue. After that, have some fun with your yellows, pinks, reds, seersucker, and madras cotton.
  • The roll of the collar, that’s the most important thing. When the collar is buttoned down, the collar will turn down into a soft roll. It may take time to find a shirt that works for you.

The Sack Suit

ivy style 2 Period Piece: The Ivy Look
Almost as important as the button down shirt is the sack suit. To be fair, the ‘sack suit’ look doesn’t necessarily need a suit. Just as passable are blazers or sportcoats paired with khakis or jeans. Here are a few things to keep an eye out for when shopping for that look:

  • Buttons are among the most important details. Look for a three button suit, with the topmost button placed in such a way that the lapel folds over it. This button is not meant to be done up, and this is called the 3-roll-2. Nothing quite as Ivy as this.
  • The preferred fit is a more loose fitting, natural look. Avoid the close-cut European suit.
  • Shoulders should be natural, with minimal padding – no padding if you can find it.
  • Venting is largely unimportant, but some insist on what’s called a ‘hook vent’, an off-center single vent. We think it’s really up to you. Pick what suits your body best.

The Shoes

ivy style 3 Period Piece: The Ivy Look
However, it’s no good if you’re finishing the look off with just a pair of high top adidas. You need a pair of shoes that will finish off the look. Crucial to finishing the look is a fine pair of shoes that identifies you as a member of that brethren that takes sack suits, button down shirts and saddle shoes seriously.

  • Converses: For sport shoes, there’s no beating a pair of canvas Converse shoes. Whether you pick the Jack Purcells or the All-Stars, it’s hard to go wrong with these classics.
  • Desert boots: Another low key choice, a pair of well worn desert boots will finish off your look nicely.
  • Penny loafers: If you want to go that extra step, pick up a pair of fine leather penny loafers. A classic casual option for the young well dressed man, a fine pair of Aldens can last decades.
  • Other options: There are a variety of other shoes that work well, including wingtips, saddle shoes, bucks, duck boots, and boat shoes. The trick is to find something that works for you.


There are plenty of little tricks, details, and nuances to the ‘Ivy Look’. Here’s some help decyphering them:

  • The Button Down Shirt: A staple, find yours in oxford weave cotton, in blue or white to start.
  • The Sack Suit: Find yours with natural shoulders, a 3-roll-2 button, and loose fit.
  • The Shoes: There’s dozens of choices available, so find something that works for you. If all else fails, canvas sneakers for sports, penny loafers for relaxing, and boat shoes in summer work.


Suit suggestions? Curious about the nature of the button down? Use the comments box below to get some help!


Xiaoli Li
Xiaoli Li is an often-missed former editor at the EveryGuyed network. He's currently working as a freelance writer, and probably yelling at a soccer game somewhere out there.
Xiaoli Li

Latest posts by Xiaoli Li (see all)

What's on your mind?

  1. I’m curious on your opinion of black Rockport “Bostonian” style shoes? Do they fIt in with the traditional Ivy prep style? Do you have any suggestions on what trousers and shirt & jacket to co-ordinate them with?
    Thanks in advance for your advice.

Add a comment

Your email address will not be published. Required fields are marked *

You may use these HTML tags and attributes: <a href="" title=""> <abbr title=""> <acronym title=""> <b> <blockquote cite=""> <cite> <code> <del datetime=""> <em> <i> <q cite=""> <strike> <strong>