You squeal at the sight of stripes, anchors and polka dots, and consider “nautical or nothing” to be your unofficial style manifesto. Lucky for you, Memorial Day weekend just so happens to be right around the corner, meaning you have free rein to pile on the prepster charm. But don’t be mistaken — you don’t have to be obsessed with colorful Lilly Pulitzer shift dresses and Barbour jackets to enjoy a classic prepster-inspired look. At the heart of the preppy movement is a love for high-quality craftsmanship, tailoring and sporty basics. Between collared polo shirts, pleated tennis skirts and Breton stripes, we’ve scouted out 27 preppy looks to round out your capsule wardrobe. Whether you’re a boho babe, self-proclaimed rocker or modern-day prepster, these statement pieces can work for you.
1. Madewell Embroidered Indigo Mercado Dress ($158): Whether you’re Mexico-bound or not, rest assured that you need this embroidered denim dress in your life. Between festival season, salsa dancing lessons and your weekly farmers’ market trip, this off-the-shoulder number will save you from every potential wardrobe conundrum under the sun.
2. Sensi Studio Pineapple Tote ($330): This handcrafted pineapple straw tote may be a splurge, but when you factor in the cost per wear (read: every beach trip, grocery run and picnic in the park), it’ll easily pay for itself. Not to mention it’ll look totes cute with all your beach cover-ups and summer chambray.
3. Mango Striped Shirt Dress ($60): Oh, this old thang? For easy styling on the go, look no further than this one-and-done yellow striped collar dress that requires zero effort. Seriously, toss this hero piece on with ankle-strap sandals for a foolproof look that works every time.
4. Madewell Waves Tee ($40): This girl is all about everyday basics that can serve double duty for the beach and spontaneous road trips. Whether you pair this slouchy waves tee with board shorts or boyfriend jeans, it’s a layering essential that will always do you right.
5. Free People Woodland Wrap Bandana ($38): As far as chic accessories go, this denim striped bandana pretty much takes the cake. Knot it around your neck with a white pinafore dress or style it with a concert tee and overalls come festival season.
6. The WhiteBrand Stars & Stripes Slider Flat Sandals ($30): Slide into summer with these striped sandals that are so “ugly,” they’re actually kind of cute. TBH, those patriotic gold stars are already growing on us. Slip ‘em on with red running shorts for a post-workout look, or keep it daytime casual with a white cold-shoulder dress.
7. Seafolly Polka-Dot One-Piece ($158): A timeless polka dot one-piece swimsuit is exactly what the doctor ordered for afternoons spent frolicking on the beach. Everything from the sweetheart neckline to the flattering silhouette (no tugging and pulling here!) has us swooning hard. All that’s missing are some red wayfarer shades and a floppy straw hat.
8. COS Oxford Cotton Shirt Dress ($115): Hello, lazy girl-approved dressing. This minimalist white collared shirt dress is the wardrobe workhorse you’ve been waiting for. You can style it for the boardroom with black tassel earrings, free-wheelin’ culottes and white glove shoes, or beach-ify your look with white sandals. The relaxed fit also makes this Oxford dress the quintessential bikini cover-up in disguise.
9. Wilfred Free Sage Short ($65): Comfort is luxury, people! Don’t be mistaken — prepsters love an off-duty look just as much (if not more) than the next girl. When getting all gussied up in your Sunday best isn’t in the cards, throw these drawstring denim shorts into the mix with a striped tank top or a mock-neck crop top for endless relaxation vibes.
10. J.Crew Le Capitaine Garment-Dyed Sweatshirt ($70): Chilly evenings spent by the campfire? Say no more! Conquer those epic summatime nights with this super cute navy nautical pullover that can be tied around your waist (or draped around your shoulders) during the day and worn with ease after hours.
11. Topshop Stripe Slouch Trousers ($70): These slouchy party pants in disguise are the foundation for a hippie-chic look — just add some disco glam platforms and hit the town. The nautical stripes scream party in the USA.
12. Clare V. Fannypack ($245): We can’t decide what we love more: the preppy madras print or the fact that it’s a fanny pack. Tote around just the essentials thanks to this hands-free sac that can be worn to the the races with a white eyelet dress or to Bonnaroo with a bodysuit and denim cutoffs.
13. Line & Dot Jacqueline Dot Maxi Dress ($231): Gear up for summer gala season with this white polka dot maxi dress that will straight-up stun with beach waves and nude scalloped heels. The imperfect dalmatian dots are a refreshing alternative to the uniform circles we’re used to seeing.
14. Topshop Cropped Polo Tee by Ellesse ($48): When athleisure meets preppy, this cropped white polo is the way-chic result. Style it with a matching tennis skirt and high ponytail for a Hamptons-bound weekend, or ditch the uniform for some thrift store Levis.
15. Boohoo Petite Star Applique Denim Jacket ($41): For a fun twist on your everyday denim jacket, try this star-studded topper on for size. Not only is it a little more rough around the edges (and in line with your rocker sensibilities), but the red stars will have you ready for every Fourth of July shindig and outdoor concert this summer. #Winning
16. Kate Spade Starfish Denim Capri ($178): Rest assured, you need not be a preppy enthusiast to pull off these white starfish printed capris. You can go super basic with a white tee, toss on a chambray button-down for a work-appropriate look or go all out with a bikini top and colorful slides for a pool party.
17. Solid & Striped The Jumpsuit ($298): It doesn’t get more fuss-free than this denim jumpsuit with a nautical-inspired knotted cutout. It’s sleek, structured and polished enough to work for day and night — brunch on the veranda or a summer wedding under the stars.
18. Tobi Kiely Striped Cropped Top ($48) + Striped Pants ($94): Taking you from a.m. to p.m., this two-piece striped set is a match made in heaven for the prepster with bohemian sensibilities. It won’t be long before you’re rocking these flowy wide-leg pants on the dance floor, at your office’s happy hour and while sipping piña coladas in Maui.
19. Jeffrey Campbell Whimsy Sandals ($125): Calling all ‘90s-esque prepsters! Next to colorful jelly sandals, these white scalloped platform sandals are giving us ALL the feels. Team these bad boys with a black jumpsuit or a pleated skort for some major throwback vibes.
20. ASOS Fringed Tassel Bandeau Beach Crop Top ($33) + Beach Short Co-ord ($36): When at the beach, you toss on the most easygoing summer separates you can find. Enter this playful white co-ord adorned with fringed tassels. Wear the set together for an upcoming holiday or style them separately for endless outfit possibilities. Team the crop top with high-waisted denim shorts for an outdoor concert, or pair the shorts with a bikini top for a leisurely stroll along the boardwalk.
21. & Other Stories Stripe Button Dress ($65): See ya later, nautical sailor stripes — we need a break. Channel your inner sophisticate with this Blair Waldorf-inspired black and white striped dress that will take you from vacationing in paradise to attending a rooftop dinner party like that.
22. Mango Straw Pamela Hat ($40): How do you beach? If you don’t already have a straw hat on standby, then this one with frayed black edges is pretty much required. Not only will it protect your from the rays, but it’s guaranteed to look stunner with a little black polka dot bikini.
23. Madewell Wide-Leg Crop Jeans in Pure White ($128): Don’t wait until Memorial Day to start wearing your summer whites. Ditch your white skinny jeans (or venture outside the box) with these wide-leg crop jeans with a cool-girl flair. Wear them with streamlined stripes, a prim and proper peplum top or an oversized boyshirt — you name it!
24. Adidas Originals 3 Stripes Long-Sleeve Tee ($45): If there’s one activewear essential that you’ll be sporting both on and off the court this summer, it’s some old-school Adidas stripes (and some Stan Smith sneaks, if we have it our way). For a top-notch athleisure look, pair this long-sleeve crewneck tee with a button-front skirt or white shorts for an afternoon spent running errands.
25. Madewell Harbor Lace-Up Shift Dress ($110): At the core of every prepster’s wardrobe is a striped shift dress that can be styled a million and one ways. Be it a yacht party or baseball game, this lace-up pinstripe number can be dressed up with platform wedges or pared down with a denim jacket and canvas sneaks.
26. Nasty Gal Private Party Headliner Swimsuit ($99): Oh yeah — you’ll be making headlines left and right thanks to this red Baywatch-inspired swimsuit that’s more than just a little promiscuous. Did you check out that scoop neckline and plunging back? It’s all sorts of fierce.
27. Quay Eclipse Cat-Eye Shades ($55): So much YAS. Blending in at the beach isn’t even an option when your cat-eye shades are this far out. The futuristic white frames and silver mirrored lenses not only call to mind an old Hollywood starlet, but they bring the bossy ‘tude.
What are your favorite preppy Memorial Day essentials? Follow us on Pinterest for more colorful style inspo!
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