Summer in the Second City can be a ‘blink and you miss it’ type of season so everyone wants to get the most out of it. Now that we are in the heat of the summer (and I literally mean the heat!), it’s the perfect time to pull out your crisp whites, pretty pastels, collared shirts, Bermuda shorts and boat shoes. This month is dedicated to the preppy look, a style that started as a niche form of dress for a selected elite but trickled down to the masses and can now be seen hitting the streets in the most urban cities.
The term “preppy” originated from the private Northeastern preparatory schools – most of them the well known Ivy Leagues. It was used mostly to describe the characteristics of the school attendees and the overall mindset of the upper class society. Though this term can be seen with negative connotations, it was never used or intended in such a way. It was merely a way of describing the type (or at least how they were perceived by the masses): well-educated, well-connected, and very wealthy. The preppy style of dress started close to 1912 and became mainstream in the Ivy Leagues in the 1950s. Retail pioneers like J. Press and Brooks Brothers made brick and mortar roots on school campuses like Harvard, Yale and Princeton, which helped to maintain and grow the trend. By the 1960s, the trend had spread to the public and beyond with screen sirens like Audrey Hepburn, Grace Kelly, and the always sophisticated Jackie Kennedy regularly sporting the styles.
Even though the preppy trend is typically synonymous with traditional upper class Northeast and New England activities like boating, polo, golf, lacrosse and tennis, it doesn’t mean you have to wait until your weekend getaway to the coast to pull out your boat shoes. This is a trend that can make whoever is rocking it look and feel polished and put together, regardless if you’re out brunching with your nearest and dearest or on a date night with your sweetheart. Brands like Lacoste, Ralph Lauren, J.Crew, Tommy Hilfiger and even Michael Kors are known for their crisp and clean preppy gear, so it’s easy to go and find a piece to add to your wardrobe. And don’t be afraid to go all out, remember, it’s not just for the Ivy Leaguers anymore!
2. Ralph Lauren Relaxed Classic Shirt, $125
4. Ralph Lauren Embossed Wool Blazer, $64.99
5. Eileen Fisher Bermuda Shorts, $158
– Carmen Turner
Image Layout: Tequila Perrin
Tags: boat shoes, Button Down Shirts, Carmen Turner, Classic Shirt, Eileen Fisher, Embossed Wool Blazer, Ivy League Preppy, Lacoste Mod Polo Dress, loafers, Pin stripes, preppy, Preppy Fashion Trends, Ralph Lauren, shorts, vintage, Vintage 1960s, Vintage Sperry Top Sider