The term preppy aesthetic is often used interchangeably with Ivy style or old money aesthetic. There’s a lot of overlap, but let’s laser focus on men’s prep specifically.
I never considered myself a preppy. Maybe it’s because Slater used the word as an insult towards Zack in Saved by the Bell. Not to mention all those rich, pastel-clad, overly tan villains in John Hughes films. Still, I did go to prep school. And I did go on to an Ivy. Eventually, I had to accept the truth. Besides, my attempts at avoiding preppy style to evade the label were for naught.
Here’s something I learned about this sartorial world, though. No matter how you describe your personal style, elements of prep can be helpful. See, it’s a style that’s inherently young but inherently classic.
A sweater haphazardly thrown over your shoulders has a youthful devil-may-care look. However, unlike a Power Rangers t-shirt or Batman mask, it’s the type of boyish visual treatment that looks just fine on a full-grown 45-year-old man. I believe prep is integral to American style and valuable to anyone’s sartorial toolbox.
So we’re all on the same page, so let’s not bury the lead. What is preppy style?
What Is Preppy Style?
Modern preppy style incorporates aesthetics and garments historically associated with the youth at old mainline Protestant preparatory schools in the Northeast. Think the plaids of private schools, the madras and Nantucket reds of New England vacation spots, and country-club-esque cable knits. It’s practical, clean, seasonal, and implies a sense of leisure and often sport. Formal pieces are incorporated, but their origins make them more youthful.
Where Did It Come From? Why Is It the Way It Is?
Preppy style originated in the 1800s and into the turn of the century. New England was the nucleus, though prep schools throughout the East Coast influenced what we deem preppy today.
Imagine what a student at Deerfield Academy might look like after school. He could be in a tie, button-down, pullover, blazer, slacks, and loafers during school. After school, he’ll take his tie and blazer off. He might untuck his shirt, switch to a nautical canvas belt and throw his pullover over his shoulders. He might keep his loafers or switch to boat shoes if he’s headed to the shore.
Still, Exeter, Groton, and Trinity kids carry many of these sartorial elements into Harvard, Yale, and Princeton. Heck, they even keep many elements when they settle down as adults in Boston, New York, or Fairfield County. In adulthood, though, preppy elements are relegated to weekend or holiday attire. You can’t wear boat shoes to the office, after all.
New England and Old England
Many old legacy families switched from the more English old-money looks to the beginnings of modern prep. New England had more seasons, so why not incorporate brighter colors, lighter summer fabrics, and pastels in the spring?
The photo book Take Ivy documented post-war prep. Then, in the ‘80s, it reached a fever pitch with the release of The Official Preppy Handbook. Moreover, it was an economically prosperous time. Hoards of nouveau riche, non-legacies started to attend prep schools and Ivys. Out-of-context popped collars and neons thus found their way into the preppy aesthetic.
Neo-prep, via the Gossip Girl craze, incorporated chicer aesthetics into the mix. Brands like Cavalli and YSL were added to the roster of Ralph Lauren, Brooks Brothers, and Burberry.
At this point in history, American prep deeply influenced the mother ship, the landed English. This is why there’s so much overlap between American prep and British countryside style. After all, Eton kids were matriculating to Harvard and moving to New York as often as Exeter kids were going to Oxbridge and London.
Basically, prep was born of the clubbier, younger part of the old money style. However, it’s not old money style as a rule since one doesn’t have to be old money to go to prep school anymore.
Preppy Style Clothing for Men
To compile a list of preppy-style clothing, consider the following: What do these kids (and kids at heart) do and like to do?
They go to prep schools, which means:
- Blazers
- Ties
- Slacks
- Loafers
- Sweater Vests
- Cardigans
- Pullovers
- Argyle, plaid, and tartan
They go to the Ivy League universities that they’re legacies of:
- Letterman jackets
- Old baseball caps with Ivy branding (the older and more worn, the better)
- Crests as a motif
- Knit ties
They holiday in places like East Hampton, Nantucket, and Martha’s Vineyard:
- Madras
- Nantucket reds
- Pastel button-downs
- Boat shoes
They play sports like rugby, tennis, cricket, golf, and squash at their country clubs:
- Rugby shirts
- Tennis sweaters and tennis whites, in general
- Pastel polo shirts
- Cable-knit
- Club ties
- Navy blazers
They hunt and ride horses on their New England estates:
- Flat caps
- Norfolk jackets
- Wellies
- Tweed
- Hunting dog or bird motifs
- Duck boots
- Polo horse motifs
They’re a coastal breed:
- Nautical motifs
- Boat shoes
- Seersucker
- Boater hats
- Dive watches (vintage is better; a family heirloom is best)
They’re never overly formal or too polished:
- Americana brown over chic black
- Penny loafers over lace-ups
- Button-down shirts over button-ups
- A broken suit over a solid suit
They either come from old American families or gain inspiration from them. So, they’re patriotic but tend to also hat-tip to England. Old money developed American prep; the oldest is the landed English. This means:
- Red, white, and blue
- American flag, Union Jack, or St. George’s cross as motifs
- Tartans
- Incorporation of English countryside style in general
- Coat of arms as a motif
- Burberry
And speaking of Burberry, here are other brands to consider to achieve a preppy fashion style:
- J.Press
- Brooks Brothers
- Ralph Lauren
- J.Crew
- Barbour
- L.L. Bean
- Hunter
- Lacoste
- Sperry
- Tommy Hilfiger
- Drake’s
- Vineyard Vines
- Rowing Blazers (an excellent example of post-Gossip-Girl neo-prep)
Now, let’s talk about putting these pieces together.
Leisure and Lifestyle
First off, you can’t go wrong with what I like to call the ultimate preppy uniform: A button-down, club tie, navy blazer, and either khakis or cream-colored slacks. Finish it off with brown leather loafers or even boat shoes if you’re at the boat club. Take it to the next level by adding a white, blue, or pastel cable-knit sweater vest. You might opt for a rugby shirt, madras shorts, and suede loafers without socks for a casual look.
You can even take something as neutral as, say, a button-down, jeans, a pullover, and
Here, we’ve preppified an outfit by making it imply prep life and also by making it a little more leisurely.
Or, in autumn, you can go for something as simple as a light yellow button-down, brown tweed pants, bright mustard cable-knit socks, and brogues. This combo is a bit vintage but not irrelevant. Colors and textures are a big part of preppy style.
Preppy Outfit Idea
Here are a few men’s preppy outfit ideas I’ve dug up from the internet machine. You’ll notice that there’s a range of actual looks. There are the stereotypical louder colors of the ‘80s preps and the more subdued looks of the turn-of-the-century school. As such, there’s a mix of vintage and modern images.
You’ll also notice that some guys mix and match. For example, a neutral cable-knit cricket sweater with navy pants and Oxfords might be subtly accented with bright socks. I also wanted to show that prep is for all ages. I may be in there a few times too.
All that to say, without further ado, here are the looks:
FAQs
Here are some oft-asked questions on the topic. Some of these are simply concise answers to topics we’ve discussed that you can use as an at-a-glance resource!
What Does It Mean if You Look Preppy?
It means dressing in a way associated with prep school kids throughout the Northeastern US. Over decades, they’ve developed a specific casual, elegant, and youthful style based on their lifestyles. This means seasonal colors, cable-knit sweater vests, nautical motifs, and Ivy League motifs, among others.
What Is Considered Preppy Now?
Preppy today isn’t that different than when it fully formed in the ‘80s. However, it’s often incorporated in fun, unique ways. Some youth wear preppy elements in more modern cuts. In the late ‘90s, the hip-hop and grunge communities incorporated brands like Tommy Hilfiger into their roster.
Is It Okay To Look Preppy?
Yes, anyone can be an aesthetic preppy. Of course, the preppy style is most natural for an actual preppy person. However, as mentioned, you can take on the look without having gone to prep school or an Ivy. And, you can incorporate elements of it into your own personal style.
Conclusion: Aesthetic Preppy
From a trend perspective, preppy style goes in and out of vogue over and over again. This, of course, is a sign that it’s classic. I know it’s not for everyone. I particularly know that pastels, madras, and seersucker aren’t for everyone. However, having youthful elements in your sartorial toolbox that won’t make you look over the hill is undeniably helpful.
And hey, you may be incorporating elements of this world without even realizing it. Low-profile white
What’s more important than the fact that prep sometimes trends and sometimes doesn’t? The fact that it’s at least never irrelevant.
Questions? Comments? Let’s start a conversation!
