Whether you're channeling Jay Gatsby (the Leonardo DiCaprio or Robert Redford version—your pick), JFK, or Chuck Bass, men's preppy style is a sure way to sharpen your summer look.
Though its roots lie in the elite Ivy League schools of the early 20th century, prep style is just as fresh today. Here's how to channel that collegiate sartorial splendor with a cool, contemporary twist.
The basics of the preppy outfit for men
First up, you'll need to lay the foundations for your preppy style.
The polo shirt
A classic pique polo gives you the comfort of a T-shirt with a touch of formality. Today's versions allow for plenty of movement and often include cooling and wicking properties. Trimmer fits emphasize athletic bodies, but even traditional sizing can make a man look sportier and youthful. Go for navy, emerald green, or pastel pink for true men's preppy style.
Team your polo with a pair of chinos with built-in stretch and a trim fit. Preppy Style 101 calls for navy, khaki, or white, but Nantucket red (actually a sort of pale pink/salmon) can nod to your adventurous side.
Dress up that basic foundation with a svelte navy blazer. While we're all for acknowledging tradition, today's lightweight, unconstructed jackets offer freedom of movement and keep things cool when the air-conditioning is on the fritz. Pull on a modern, fitted sport coat to complete your preppy outfit. Feeling confident? Forgo the navy for a defiantly preppy plaid blazer.
The plaid button-down
Speaking of plaid, a madras plaid button-down is another essential for the preppy outfit for guys. A long-sleeved version has year-round potential, but short sleeves will suit summer's steamier moments (after all, the fabric was originally designed for the tropics of India). Wear the glowing pop of colors with toned-down khaki shorts or white jeans to keep things light and neutral. A gingham shirt in blue and white is another worthy substitute.
A word on denim
True preps prefer to keep their denim simple and neat. Again, fit is key, so opt for a trim style rather than anything ultra-baggy or super-tight. Dark or faded wash are both acceptable (but leave the distressed jeans for another day) and if you like added details, go for a cuff with selvedge denim. Dress up slim, straight-fit jeans with a snow-white polo shirt and—if it's cool in the evening—a long-sleeved cashmere V-neck sweater.
Formal prep style
Weddings, fundraisers, garden parties, the Kentucky Derby—summer usually brings with it a least a few formal occasions and men's preppy style is a sophisticated solution for most of them. Your secret weapon? The seersucker suit, which is designed to be cooling and comfortable, with its roots in the hot climes of Louisiana. The most common version is pale blue-on-white puckered stripes, but red, yellow, or green stripes all have a place in the prep-school style manual. More recently, darker black-on-navy or black-on-black versions have waltzed confidently onto the fashion scene.
Pair your suit with its natural complement: the Oxford-cloth button-down, originally created to keep the collars of polo players' shirts from flopping around when on horseback. The cloth itself is a tight, textured basket-weave. While a white version will be the most versatile, if you're whole-heartedly embracing men's preppy style, you can round out your closet with a button-down in pastel pink, yellow, and blue.
The great thing about an Oxford-cloth shirt is that it mellows with age. Once it's been retired from its more formal purposes, the button-down becomes perfect for knocking about on weekends.
The beauty of layers
Men's preppy style rests on one other universal principle: layering. It's practical—you can add and subtract layers depending on the temperature—and it also gives you the chance to experiment with several tried-and-true classics at once. Pop a polo shirt under your gently worn Oxford button-down for cooler mornings. A deep V-neck tennis sweater over the top evokes a sporty air (wear it with white flannel trousers for a Jay Gatsby look). And a Breton-striped T-shirt peeking out from beneath can allude to your sailing cred.
The finishing touches
These final flourishes are where a preppy look for guys can really exude some flair.
Go ahead and embrace the open collar on sweltering days, but that seersucker suit and Oxford shirt will look especially sharp when teamed with the right tie. The diagonally striped "rep" tie works best here—the geometric flash of color adds an element of self-expression. If you're feeling extra jaunty, go for an elegant bow tie in silk stripes or cotton plaids.
Embrace the sporty side of men's preppy style with a striped ribbon or webbing belt. For casual prep, the D-ring belt goes perfectly with your polo and khakis or denim. When striving for a more polished look for your summer suit, opt for a sleek leather in rich brown.
While classic Oxfords are a prepster's go-to, you can get also a little cheeky with footwear. White bucks (a summery version of the formal lace-up) are an excellent, dressier stand-in for sneakers, but to really up the style stakes, invest in elegant loafers in suede or leather and eschew the socks. And when the dress code is more relaxed, deck shoes, camp moccasins, and canvas sneakers will serve you well.