While I’ve never attended prep school, as a New Englander I’m no stranger to the occasional popped collar or monogrammed accessory. Preppy style just goes so naturally with this coastal area, like dropping “r”from the end of words and complaining about the weather. Windswept beaches and Hunter boots? Madras plaid and Cape Cod? Nude flats and…everything? All the yes.
But it’s too easy to go overboard and start looking like a Stepford wife in head-to-toe classics. So I started with ten essential preppy pieces and found updated versions with a twist or maybe a teeny bit of edge. Traditional can be a good thing, but shaking things up is refreshing – let’s give it the old college try, shall we?
Updated Preppy Essentials for Summer
(Clockwise from top – you can hover over any of the images for the link)
The striped top – J.Crew Striped long-sleeve off-the-shoulder top: Navy stripes and summer are a given, and they’re so fun in this easy, wearable tee. Lazy girl tip: just wear your regular bra and pull slightly off your shoulders to keep the straps hidden under the top.
Ray-Ban sunglasses – Small New Wayfarer 52mm sunglasses: Still classic black, but the petite size in the new Wayfarers fits better on smaller or narrow faces so you don’t get that bug-eye look. And Ray-Ban’s site lets you virtually try sunglasses on so no unwanted surprises when you pop them on for real!
Everyday flats – J.Crew Factory Pom-pom suede colorblock flats: While I will never not love a nude ballet flat, these black & tan ones are a little bit cooler, no? And just as versatile.
White jeans – Joe’s Icon skinny ankle jeans White denim is pretty much a preppy summer staple, but these distressed ones are eons cooler. As a recovering prep, I got my first pair of ripped jeans last month and I’ve worn them weekly. Joe’s Icon ankle skinny jeans fit so well and they’re perfect for warmer weather.
Madras (and gingham!) plaid – J.Crew Gingham French Bikini Top: Bright watermelon, turquoise and navy, of course, on a modern cut bikini top (on sale!) and J.Crew Plaid Tassel Flats: Such a cute update on madras plaid, and on sale! Love that beaded orange tassel. Reviewers are obsessed.
Buttondown shirt – Bell sleeve shirt: Try this summer’s update on the basic buttondown – this version’s interesting and dramatic but still not too far out of most comfort zones. I tried on a bell sleeve shirt like this in person and loved it. It’s so cool in black, too.
Tote bag – Sea Bags recycled sail cloth tote: Of course I still have the monogrammed L.L. Bean tote that’s basically a rite of passage up here, but I’ve been loving my Sea Bags tote made out of recycled sail cloth in Maine (you may have seen it in a recent insta post!) It’s incredibly durable and comes already broken in, so any smudges from sticky little fingers or sunscreen blends right in.
Hunter rainboots – Hunter Original Short adjustable back rainboot: A shorter height, wedge heel and studded back strap toughens up the traditional tall Hunter boots.
Straw bag – Rattan clutch: The standard color is pictured here, but it also comes in a bright pink that would instantly update any white sundress or blazer. I’d wear this color with anything and everything though, I like the boxy shape and leather strap.
Stud earrings – Rose gold pyramid stud earrings: Delicate edge made infinitely wearable. I have a similar pair and they’re quickly becoming my go-to for everyday wear. Rose gold is so pretty in the summer too, with a tan or without.
I found more updated preppy picks than I could fit in a collage, so I rounded some more options up for you here.
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