Preppy Classics...with a Twist!

There’s nothing I love more than a classic wardrobe staple with a wink. This season, preppy favorites are getting playful little updates, from bow-trimmed linen shells and fringe-hem paisley pants to eyelet anchors, sculptural pearls, crochet totes, and silk scarf belts. They still have all the polish and ease of the pieces we reach for year after year, but with unexpected details that make getting dressed feel extra fun. Think of it as timeless summer style, just with a little more personality.

The double-bow neckline on this linen blend sleeveless top (more sizes here) is such a chic twist on a classic shell. Pair with these navy paisley silk pants with a flirty fringe hem. They're bohemian but polished enough for dinner out. I loved picking up the red in the print with these strappy flats and simple stud earrings.
I have this navy eyelet halter dress in my cart. Zoom in on the gorgeous eyelet anchor motif and little gold knot buttons. I'd pair with my trusty gold wrap sandals.
Rich blue florals make this cotton blouse feel special without trying too hard. I'd wear it with white jeans now, white shorts come summer, then dark denim in the fall.
Think diamond huggie hoops, but totally unique. I'm obsessed with these bezel emerald huggies which feel unexpected, but are still something you can (and will want to) wear everyday.
I wore these polished boat shoes on my travel day going to Nantucket and they have the run-around-all-day comfort of a sneaker, while looking more elevated than your typical boat shoe thanks to the flattering almond toe.
This two-in-one blue and white shirtdress is ingenious. Tie the shirt over the dress to protect your shoulders from the sun by day, then remove the shirt and add a statement necklace to transition seamlessly to dinner al fresco. Such a smart piece to pack for summer adventures! (You can always pair the shirt with high waisted trousers as well.)
Elevated denim at its finest, this A-line skirt has a beautiful drape and a polished silhouette. Pair with a tucked-in blouse and heels, or keep it relaxed with a striped tee and flats. (For a slightly more casual version at a much more attractive price point, this midi skirt is under $200, and it's one of my most-worn pieces.)
This blue and lemon marled raffia hat is a fun alternative to a natural straw hat. Pair with anything navy!
Denim dresses are a wardrobe workhorse whether they're a fresh fit and flare style in white denim (very chic) or one of my favorite Zimmermann silhouettes in a soft chambray.
Consider this white eyelet caftan your new warm-weather uniform. I tried this on at the new Nantucket store and the mandarin collar and button front elevate it beyond a cover-up, so it transitions easily from the pool to lunch. (There's a slip too!) I have that caftan and these gold sandals in my cart.
This season’s espadrilles are anything but basic, with fresh details that make the warm-weather staple feel especially fun. I love the texture of these crochet espadrille flats for a polished coastal look, while this affordable red d’Orsay pair adds the perfect cheerful pop of color with dresses, denim, and breezy summer whites.
For a fun twist on pearls, this hand-twisted silk cord collar necklace with a freshwater pearl drop is so playful. I also love this sculptural pearl necklace as a modern update on the classic strand.
The chunky weave on this straw tote reminds me of this bag by The Row, but for only half the price.
A simple tee and gingham skirt is an effortless summer combo, but make it fashion-y with this patch-pocket midi skirt.
The ric-rac trim on this blue gingham midi dress gives it the sweetest vintage appeal. Adjustable tie straps make the fit easy, and it's darling with flat sandals or espadrilles.
A simple shift dress is one of my summer staples, and this navy and white shift has the most beautiful nautical rope pattern. I saw it over the weekend on Nantucket and it's a lightweight but substantial fabric perfect for warm days ahead. So chic with patent slides like these.
The scrolling embellishment and a bold blue print give this midi skirt such a dramatic, beautiful silhouette. Pair with simple black sandals and gold hoops to let the details shine.
Fisherman sandals are having a major moment, and this sleek bone suede pair is the most refined version I've seen. Perfect with everything from midi skirts to cropped trousers all summer long.
Dress up a classic white shirtdress with this unexpected scarf belt for a look that's equally fabulous on vacation or at the office. You can use any 90cm silk scarf, but I'm extra excited about the sailboat pattern on this one for summer.
An eyelet button-down like this boxy shirt is an easy upgrade to a classic white button-up. Especially good with high waisted linen pants or denim.