Ivy League Style: Preppy Looks

Written by Dan | 21/05/2023


Ultimate Guide

Are you looking for a timeless and classic style of clothing? Do you want to be comfortable and stylish at the same time? If so, then the preppy style might just be the perfect look for you.

Preppy fashion has roots in traditional Ivy League colleges like Harvard, Yale, and Princeton. It’s characterized by its clean lines, bright colours, and relaxed silhouettes. The preppy style is all about looking polished without having to try too hard. This guide will provide an overview of preppy fashion – from its origins to tips on how to achieve the preppy aesthetic!


A man wearing a Fred Perry jacket

Overview of Preppy Style

Preppy style is a quintessential American fashion, originating in the Ivy League schools of the East Coast during the 1950s. It takes its name from “preppie”, a playful nod to Prep, short for Preparatory School.

Characterized by an understated casual look with brightly coloured polo shirts, knit sweaters, boat shoes, and khaki slacks, the preppy look was popularized by movie icons such as James Dean and Audrey Hepburn.

The key elements consist of striped designs, plaids and collegiate badges usually incorporating a navy blue, burgundy red and light beige colour palette.

Cable knit wool jumpers are another staple – often striped and always in bold colours like green, yellow or pink. They make all the difference to this classic yet distinctly individual look.

Big brand names have long been associated with preppy styling. Ralph Lauren polo shirts and Tommy Hilfiger tees and sweatshirts are the perfect way to get started.


How to Dress Preppy Today

Preppy fashion is the perfect balance between trendy and classic. It’s having a major moment right now as the style of choice for several generations and continues to re-emerge as a popular look.

In order to dress preppy today, invest in timeless wardrobe staples such as polos, chinos, boat shoes, knitwear, button-down shirts and blazers. Stick with solid colours like navy blue and white for added charm or choose bold hues such as pink and mint green for more vibrant looks straight out of the official preppy handbook.

To add interest to an ensemble, choose from eye-catching patterns such as gingham, stripes or argyle. With preppy wear, you want to appear polished yet understated. Be sure to stick with key pieces in subtle prints and colours that are tailored to your unique aesthetic.


A man oozes preppy style on some steps

Preppy Outfit Inspiration

If you’re looking for an effortlessly stylish look, then preppy outfits are definitely the way to go! The classic preppy style is a popular look among many, due to its chic and versatile nature.

There are endless possibilities when it comes to creating a preppy outfit. Think tucked-in collared shirts in pastel colours with contrasting chinos or jeans. Pair with loafers or boat shoes, chino shorts, or cardigans topped over a rugby shirt.

A denim jacket is the ideal outer layer for a preppy look and you can also experiment with different fabrics such as linen, corduroy and cotton.

While it may seem simplistic at first glance, there is so much potential that can be channelled into creating the perfect preppy look – one that won’t fail to turn heads!


A man wearing a Ralph Lauren shirt and sunglasses

Accessorising a Preppy Look

When it comes to pulling off a preppy look, accessories make all the difference. Neutral colour shoes are key to adding a preppy touch – oxfords, loafers and boat shoes work perfectly!

It’s important to pick a classic style when it comes to dress shoes and they should be paired with solid-coloured dress socks. Colourful patterned or striped socks can add a fun twist to an otherwise everyday classical outfit.

An embroidered Ralph Lauren polo shirt is also essential for the ultimate preppy style, preferably in neutral colours like whites or blues. Equally on-trend is the Tommy Hilfiger sweater. Clean lines and traditional Ivy League colours lend themselves perfectly to the overall look.

Mainline Menswear stocks several styles of baseball caps that would be perfect to complete your outfit. Clothes, shoes and accessories from the biggest brands. What more could you want?


Final Thoughts on Creating an Ivy League-Inspired Style

It is easy to be inspired by preppy-style greats like those associated with Ivy League universities. However, when creating an Ivy League-inspired style, it’s important to remember that it should be tailored to each individual. After all, a classic look is all about expressing one’s own personal style.

In conclusion, combining classic and modern elements of fashion will create an entirely unique look that can come together to create something truly special. Ultimately, there is no wrong way to create an Ivy League-inspired look for men; because there is no one perfect fit for anyone.



Find your preppy style at Mainline Menswear

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