With dress codes becoming increasingly more vague by the day, it’s sometimes difficult to know how to dress for certain occasions. Do I or don’t I need to wear a jacket? Am I going to be underdressed wearing sneakers? Do I have to wear a tie? If not, what shirt shall I opt for instead? There are so many questions to be answered without much certainty, as so much of it is down to interpretation. One thing is for certain, though, and that’s that you can never go far wrong with prescribing to the preppy or Ivy look for it has the miraculous ability to straddle the lines of formal and casual (and unless the dress code is black tie or lounge suits, you’re going to be allowed through the eagle-eyed judgement gates).
Despite its roots which dive deep into the history books to circa 1910, whereby affluent and privately educated northeastern American students started to dress in a certain way to help themselves stand out from the rest via incorporating elements from sportswear and casual wear into their uniforms, the style has never been more in vogue than it is today. As the 20th century came to its halfway mark, preppy became Ivy, and this subculture has grown significantly. It hit the mainstream and numerous menswear brands had began to cater to the demographic whom sported the styles — many of which come from sportswear — which had a cool, sophisticated but nonchalant way about them with pops of colour for added attention.
Dressing with a preppy aesthetic today has its contemporary and classical qualities in equal abundance. Ralph Lauren has always done more than its part in keeping the style firmly within the zeitgeist, while Drake’s, a firm favourite of ours for innumerable reasons, has always paid reference to preppy culture with its collections that are ripe with references and fun commentary on the varying staples within one's wardrobe. In terms of pop culture, we’re always fed imagery of the likes of John F Kennedy, who sported preppy staples with aplomb, in addition to the likes of Paul Newman. So, forgive me for using a term that’s far too liberally thrown around these days to describe various codes of classic menswear, but preppy style really is timeless. And with this in mind, here are five preppy staples that you should incorporate into your wardrobe.