Style Guide For Grown Men To Dress Preppy Like Ivy Leaguers

The preppy style is definitely one of the classic trends that have endured the test of time. Inspired by the sub-culture and dressing style of America’s east coast elite, the preppy look is all about classic colors, patterns and apparel that never go out of style.

Keeping up with the times, preppy style can be adopted in a modern and youthful manner by today’s classy man. The trick is to wear classic trends in a non-traditional way, apt for a grown man and to not look like a college kid.

Underlying principles that will help guide you in making the right choices when it comes to this style:

  • Always work around classics. For example, a button-down oxford shirt or a polo shirt is a classic preppy piece but a graphic tee is not.
  • Keep your preppy clothes fitted as per today’s trends to make them look modern and not too costume-like. Nothing works better than a nice clean cut.
  • Choose traditional colors for a polished look. Although experimenting with colors is not ruled out.
  • Layering your look works well. For example, you can wear a crewneck sweater over a button-down shirt and then further layer it with a blazer.
  • Keep the collars down. Never pop those collars up. It is one of the most anti-preppy things to do.

10 Essentials for a preppy Ivy League look

  1. Oxford shirt – the ultimate prep staple

Preppy pursues a classic style which is not too formal. So opt for a button-down oxford shirt for a perfect formal-casual blend.

Oxford Preppy Style

Oxford Shirt


  1. Polo shirt

Polo shirts are perfect to be worn casually in summers if you want to ditch the oxford shirt. They are sporty and can easily be paired with chinos.

Polo Shirt mydailycrew

Polo Shirt

  1. Crewneck sweater

Wear your sweater with an oxford shirt. If you want to layer further, you can add a jacket on top of your sweater. You can also wear a tie if you want. Crewneck sweater can be worn with chinos as well as jeans. Just make sure the jeans are solid colored and not faded or ripped.

crewneck sweater mydailycrew

Crewneck Sweater

  1. Cable sweater

You can wear cable sweaters both formally and casually. Pair them with chinos and loafers for a casual look. Or you can wear a cable sweater layered with a oxford shirt underneath and a blazer above for a more formal look.

cable sweater Preppy style

Cable Sweater

  1. Navy blazer

Pick the blazer in a good quality fabric and the right fit for you. Wear your shirts tucked-in with a navy blazer. You can pick blazers in other colors too, there are no rules stopping you here.

Navy Blazer preppy style

Navy Blazer

  1. Chinos

Chinos are probably the most versatile pieces in the preppy scheme of things. Pick chinos in pastel colors and earthy tones. Opt for a tailored fit but not one that’s too slim. They look more formal than jeans but casual as compared to formal trousers. They can be paired with everything from blazers to sweaters to varsity jackets. You can also add suspenders to your trousers for a more Ivy League look.

Preppy Style guide


  1. Seersucker

Seersucker is a lightweight fabric with a crimped surface. It is breathable and far less structured than suiting. You can find jackets, trousers, shirts and suits in this fabric.

seersucker preppy style

Seersucker Shirt

  1. Varsity jacket

Varsity jackets remind everyone of college and football teams. This piece is obviously on the casual side. Pick a varsity jacket in traditional classic colors like deep brown and navy; and style the rest of the outfit around the jacket.

varsity preppy jacket

Varsity Jacket

  1. Loafers

Casual shoes like loafers, simple trainers and espadrilles are the usual go-to shoe styles in the preppy lookbook. You can wear vintage inspired shoes for a more classic look.

Penny Loafers Preppy style


  1. Accessories

You must pick a couple of accessories to polish your outfit.

  • You can opt for a nice watch with stripes for a casual look and one with a leather strap for a formal look.
  • Choose ties with stripes or with nautical patterns. Bow ties also make for great preppy additions.
  • Pick leather belts that match your shoes.
  • Pick pocket squares in colors and patterns that complement the rest of your outfit.
  • Wayfarers and classic round tortoiseshell are the only styles of sunglasses you need to choose from.

Fossil watch preppy style

Fossil Townsman Watch



bow tie preppy style

Bow Tie


ray ban preppy style



Remember that the preppy style is all about class. You can experiment with fabric, color and pattern all you want but the idea is to have a style that looks eternal nonetheless. That also comes with grooming yourself well and having an attitude that exudes nothing but class.


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Preppy Style for Men

2018-05-21T09:36:27+00:00 Fashion, Men, Workplace|