Preppy Style Guide

If you're feeling preppy, check out my quick and easy tips, in this Preppy Style Guide, to have you looking like a Kennedy in no time!

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Feeling preppy?

Late summer has me dreaming of trips to Nantucket, BBQ's, and maybe a few gin and tonics. While "preppy" attire has occasionally been coopted by magazines and brands trying to sell their own products (read: J Crew's weird neon and chunky necklace phase in the 2010's), true "preppiness" is not something you can buy at just one store.

Preppy attire is never over-the-top, quick, fast fashion. It's always high-quality clothes, worn until they're a bit worn out, and then kept even longer. It's having just the right clothes to thrown on for any event, as your black sheath dress goes everywhere.

And if you're interested in more than the clothing aspect of the preppy aesthetic, check out the updated classic, The Preppy Handbook, updated for our generation.

At the bottom of the post, I've rounded up some of my preppy essentials - so don't forget to check them out!

Preppy Style Basics

So let's talk through the basics of preppy style essentials. A few tenants to keep in mind, all of which are true regardless of the specific outfit:

Never flashy

Head-to-toe Nantucket red, needlepoint belt, and over-the-top Irish fisherman sweater is, though perhaps technically preppy (?) a bridge too far. You should never look like you're playing Warner's evil, East Coast fiancee from Legally Blonde.

Avoid fast fashion

While the current trend certainly is the environment destroying fast fashion of the moment ("you need this leopard headband!!!"), remember that preppy style is timeless, and, ultimately, environmentally friendly.

You need to buy an item and wear it out. But to do this, you need to purchase high-end, hard-wearing items that will last a decade. Or longer. You don't have to go the full Prince Charles, who has joked that he happens to be in style every 25 years because he always wears the same clothes, but lean closer to that, than to buying the cheapest, soon-to-be-disintegrating sweater an influencer is hawking.

It's not about the label

While in popular culture, people definitely have a tendency to conflate "preppy" and "rich," loading up on gaudy designer labels is the opposite of flashy. Feel free to buy a Burberry coat - but make sure the signature plaid is on the inside.

Preppy Style Essentials

Now that we've got the basics rules in hand, it's time to discuss the preppy style essentials themselves! Likely, you'll already own a few of these.

Preppy Style Essentials: Pearls (real)

Perhaps the most classic preppy essential (for women) is a pair of pearl stud earrings. Classic and timeless, without being flashy or even terribly expensive, you can't go wrong. And, of course, every girl needs a few strands of pearls, both a long and a short, at least, for everything from weddings to graduation parties, and sometimes Tuesdays.

Preppy Style Essentials: Boats, Horses, & Cocktails

From clothing to house wears, if it doesn't fit into one of these three themes...skip it.

Preppy Style Essentials: College gear (your own)

The Wren Building at The College of William & Mary

I'm stealing this tip from the original Preppy Handbook - rocking college gear is classic preppy attire - as long as it's your own. Or at least one with which you have a legitimate association. There's nothing more awkward than being approached by an alumni and having to admit you just like their shirts. Cringe.

Preppy Style Essentials: Boat Shoes

One of the best preppy essentials is a good set of topsiders/boat shoes. Waterproof loafers are surprisingly comfortable, versatile, and durable.

And don't even think about wearing socks.

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Preppy Essentials: One monogram per day

If it doesn't move, monogram it. Cuffs, totes, hats, silver earrings, Jefferson cups - you name it, I can find a place to get it monogramed. Just don't combine them all in one outfit.

Preppy Style Essentials: The right brands

Preppy mainstay brands are classic, though some brands geared toward preppy dressers will come and go. Purveyors of preppy essentials:

• Brooks Brothers
• Ralph Lauren
• Sperry
• Lilly Pulitzer
• Jack Rogers
• Barbour
• Smathers & Branson
• Ray-Ban
• Hermès

Preppy Style Essentials: Sunglasses

From JFK and Jackie O to Princess Grace, it's all about the shades. Ray-Bans are the preppy go-to for men and women. It goes without saying, I hope, but black and tortoiseshell...no rhinestones, please.

Thanks for stopping by!

I so appreciate that you took the time to check out my preppy style guide! Please explore the rest of the blog while you're here! xx

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