20 Modern Preppy Outfits For Men: How To Get The Ivy League Look In 2023
Preppy style isn’t what it once was. Originally a mainstay of the Ivy League schools during the 40s, 50s and 60s – where students would try to one-up each other in the fashion stakes using sharp navy blazers, letterman sweaters and club ties – modern-day prep is something else entirely.
Although it certainly incorporates those classic menswear pieces into its lexicon, today’s preppy aesthetic is as much about streetwear as it is old-school tailoring. But how did we get here, and how can you pull off the look in 2023?
What is preppy style today?
Like many aspects of menswear, preppy style has changed over the years. Gone are the days of fairly rigid, public-school attire, worn to make you look like a freshman at Yale. Prep is no longer just about polos, madras shirts, tweed blazers and penny loafers. It’s evolved.
Over the last few decades it’s seen many guises. Designers like Ralph Lauren flew the flag early on, thanks to his obsession with the ‘American look’ and the aspirational connotations it promotes. But when hip-hop took hold in the 90s, elements of his vision were adopted and chopped up, especially on the East Coast. Rappers like Raekwon spliced Ralph Lauren Snow Beach jackets with baggy jeans and Timberlands, showing the potential for preppy fashion to exist outside of its intended context.
It wasn’t until the 2000s that it went through another spin cycle, this time with artists like Kanye West and Pharrell, who regularly sported colourful polo shirts, Oxford button-downs and backpacks with their iced-out necklaces and expensive watches.
It’s zeitgeist moments like these that have helped preppy style become what it is today. Forget bow ties and braces, prep 2.0 is more sophisticated than that. The brands that do it best fuse elements of street culture – whether that’s retro sports logos or throwback sneakers – with classic, tailored attire. They might, for example, style a grey herringbone blazer with a hoodie, or a varsity jacket with a double-breasted camel overcoat.
Fits are more relaxed and less rigid, so an oversized tee might be tucked into a pair of light-wash jeans and finished with white sports socks and loafers. Baseball caps are fair game, and are often teamed with sports coats and Oxford shirts.
Yet the best thing about new-age prep is that it can be worn by anyone. Ivy League style may have started as a way for the elite to show off their social status, but today it’s approachable and for the everyman. Walk into your nearest thrift shop and chances are you’ll find everything you need to give it a go on a budget. The goal posts may be moved once again in the future, but for now you’ll find us in a vintage rugby shirt, pleated chinos and loafers.
Men’s modern preppy outfits
In need of some inspiration? Here are 20 looks that encapsulate exactly what preppy style is in 2023.
A denim jacket is your friend when it comes to preppy style. Forget club blazers and tweed, a jean jacket adds a more casual flair to tailored trousers and loafers, especially when combined with a striped polo and logo’ed baseball cap.
Take inspiration from those 90s Ralph Lauren ski jackets and opt for a colour-blocked version, which works as both a statement piece and a way to protect you from the cold. Combine it with tailored corduroy trousers and a beanie and you’ll be the coolest guy in the room, whether you happen to be in a ski chalet or not.
Mix it up
This look, with a tweed or club blazer, would be the definition of classic prep. But swap out the tailoring for a fleece jacket and it’s instantly injected with a more contemporary feel, which perfectly complements the worn-in jeans and baseball cap.
Varsity jackets have a long lineage in the world of prep. The good news is you don’t have to be a sophomore on the college’s baseball team to wear one.
Look for simple designs in muted colours like bottle green and combine it with tailored trousers, roll necks and suede boots.
Preppy style might traditionally be all about colour – from loud madras shirts to vibrant polos and punchy tweed – but for a contemporary update, try a muted monochrome look consisting of a grey plain varsity jacket, black shorts, white tee and penny loafers.
A key part of prep 2.0 is high/low dressing. That essentially means combining something high brow, such as tailored trousers, with something more casual, like a streetwear hoodie. This look shows why this combo is such an easy route into the preppy game.
Classic Ivy League
If you are a stickler for tradition, there’s no harm in keeping things old school. Go for a classic American tailored look with a sharp double-breasted boating blazer, Oxford shirt, chinos and loafers, and you can’t go wrong.
While not a classic look on paper, it’s all about the details here. The smallest of things can infuse a bit of prep into an outfit, like the subtle silk, cravat-like neckerchief tied underneath the Cuban collar shirt here. Once the preserve of Ivy League professors and now a summertime flex.
Preppy summer staples
A simple spring or summer look, this outfit makes use of classic prep staples – a striped linen shirt, pleated shorts and canvas belt – and renders them in a warm-weather context. Finish with a pair of cream espadrilles and tortoiseshell shades for an Italian-inspired twist.
Relaxed preppy tailoring
When it comes to preppy tailoring, it’s best not to try too hard. It can be all too easy to fall into Carlton Banks territory, and not in a good way.
To stay the right side of stylish, stick to classic shades of navy and off-white and pay attention to the fit. Consider more relaxed cuts than you’re perhaps used to, combining wide-leg trousers with a boxy, unstructured blazer, as shown here.
The rugby shirt
The rugby shirt is the UK incarnation of the varsity jacket, or the letterman sweater. It’s a public school classic, and one that the upper class have appropriated for weekend wear for decades. But do it well and it’s so much more than that.
The madras shirt
While it’s undoubtedly risky business, the madras shirt is a style classic. Typically cut from jazzy fabrics featuring loud check patterns, the style is perfect for a splash of summer colour.
Try it yourself by keeping the rest of the look muted, anchoring your top half with neutral tailored trousers and leather boots.
Preppy colour palette
The preppy aesthetic has long been defined by bright, bold shades – from scarlet red through to burnt orange – whether via polo shirts or the fibres in its tweed jackets.
Try it for yourself by injecting a splash of colour into your top half with a statement hoodie. Keep everything else simple and finish with canvas high-tops for some old-school flair.
The best bits of mod style were borrowed from prep, from the penny loafers to the jackets and sharp tailored trousers. Combine the lot, throw in a knitted polo for good measure, and you can get your own bit of 60s Carnaby Street action, whether you’ve got a Vespa or not.
Here’s a contemporary take on prep that’s perfect for 2023. It works largely because of the colour palette of browns and naturals, but also because of the texture. The cotton jersey of the sweatshirt (a prep staple), complements the corduroy of the jacket, while the bi-weave trousers work perfectly with the suede loafers.
Prep has heavy roots in the sporting world, from its letterman jumpers to its varsity jackets. And while sweatpants don’t scream Ivy League, they add a youthful feel to a rugby shirt and sneaker combo, making it ideal for a relaxed weekend look.
Moneyed smart casual
There’s something about a polo shirt tucked into a pair of stone trousers that screams ‘Gatsby on his day off’. While the jumper tied round the shoulder may be taking it a step too far, this is a timeless prep look that’s ideal for many a summer sporting event.
The sports coat was a core part of the original prep aesthetic, and it’s a garment that translates well to today’s world with the continued casualisation of dress codes.
An unstructured, knitted blazer such as this can be thrown over everything in your wardrobe – from jeans to chinos – helping you instantly smarten up without looking stuffy. Combine it with textured wool trousers and a knitted polo shirt and you have an outfit that works just as well for business lunches as it does dinner and drinks with your partner.
The preppy shirt tuck
Sometimes it just takes a shirt tuck for a look to get the preppy treatment. So, next time you wear a button-down shirt, try tucking it into mid-wash jeans and you’ll instantly feel a touch smarter and more refined.
Old meets new
This is a definitive prep look that references old and new. Incorporating almost every garment associated with the Ivy League, it sees a madras shirt tucked into mid-wash jeans, with both a varsity jacket and camel overcoat layered over the top. Not only that, it’s then finished with loafers and a tonal baseball cap.
Half street, half classic, it showcases everything that’s great about prep style in 2023.