Preppy Pieces

When you hear the word "preppy," a few things immediately come to mind: pearl necklaces, penny loafers, and characters like Blane and Steff from Pretty in Pink. In other words, it conjures up a look that hasn't been wildly popular since the '80s--until now. Thanks to the combination of Tommy Hilfiger's Prep World (a pop-up store touring the globe with a capsule collection of the designer's prep-inspired classics) and the popularity of two style books (True Prep: It's a Whole New Old World, which is the follow-up prep guide to Lisa Birnbach's The Official Preppy Handbook, and the first English translation of the seminal Take Ivy), the preppy look is finally returning to the spotlight. Even better, designers like Tory Burch are creating seriously cool options with nary a whale print in sight! In honor of this summer-friendly trend, we've sourced some of the best of-the-moment, ultra-affordable preppy pieces for your purchasing pleasure. Whether it's a pair of nautical-chic wedges or a polished plaid dress, these handpicked items will freshen up your mid-season wardrobe without breaking the bank, so feel free to shop today's Under $100 story sans stress. Whatever you buy, just know that Muffy would definitely approve...

Brixton Delta Straw Hat ($42) in Brown
While you might have spotted a preppy teenager sporting a visor at the country club back in the '80s, today's prepsters are likely to be wearing this charming straw hat by Brixton. This topper will effectively shield your face from harsh summer rays while keeping you chic in the heat. Go incognito and team it with a pair of oversized shades for a foolproof beach-day look!

J. Crew Stripebreaker Sweater ($78) in Champagne Honey
Nothing says "preppy" like a striped sweater in a bold, primary color, so we simply had to bring you a top-notch option. That said, we happen to think this Stripebreaker Sweater from J. Crew is the cream of the crop! Made out of lightweight, breathable cotton and boasting honey-colored stripes, this piece is definitely a must-buy. It will also last you well past summer--come fall, simply layer it under a jacket and you'll have a superb ensemble in no time!

Forever 21 Shorts ($15)
Though these Forever 21 shorts aren't plaid, covered with tiny crabs, or Nantucket reds, they are certainly a nod to the preppy look, thanks to the pleated front detail, cuffed hem, and airy linen fabric. The ideal balance between structured and relaxed, these shorts will work for any number of occasions this season!

River Island Green Padlock Bag ($40)
While roomy beach totes are a great option if you're headed to the coast, we think a small bag in a bright color is ideal if you plan on sightseeing in the city. This version by River Island fits the bill perfectly; its Kelly green color (a signature preppy hue) is irresistible, especially when paired with pale pink pieces. We also adore its padlock detail--a subtle nod to the stables--and compact size! We suggest picking up this purse ASAP and carrying it across-body for a fuss-free summer outing!

D.V. by Dolce Vita Nero Platform Wedge Sandals ($79) in Navy
Everyone knows that wedges are a summer wardrobe staple, a fact that's decidedly true when finishing off a preppy look. Accordingly, we selected this nautical-inspired pair by D.V. by Dolce Vita. The navy color and contrasting white stitching is quite cute and will work with tons of ensembles this season. Team them with anything from white cropped pants to denim cutoffs and you'll have a winning outfit in no time!

ASOS Check Dress with Bow Belt ($78)
If you ever had to wear a uniform in high school, you've probably renounced the plaid skirt altogether; however, we simply adore ASOS' Check Dress for a serious upgrade on the schoolgirl look! Featuring a tough-girl leather bow at the waist and a desirable mid-thigh hemline, this dress is our latest obsession from the beloved online retailer. We suggest wearing this charming frock with flats now or tights and boots in the fall.

Casio Analog Leather Strap Watch ($40) in Cognac Snake/Gold
Think you have to spend a fortune on a sophisticated watch? Au contraire! All you need is this Casio, as it has a classic gold face, luxurious leather strap, and a decidedly affordable price tag. Trust us, you won't want to take it off, as it will go with literally any outfit and is waterproof to boot!

Coincidence & Chance Scalloped Chiffon Blouse($59) in White
Collared shirts are always a classic choice, but we love a feminine twist on this wardrobe staple, hence, our inclusion of this blouse by Coincidence & Chance! We're smitten with its Peter Pan collar and scalloped details, which give the shirt a whimsical vibe we can't resist! Pair it with a red pencil skirt for an on-trend, color-block look for the office, or team it with denim shorts for a fantastic weekend ensemble. However you style it, we promise you'll fall in love with this versatile blouse!

Tommy Hilfiger Web Belt ($48) in Red
During the warm-weather months, we tend to have a penchant for easygoing, loose-fitting tops and dresses, which is why a great waist-defining belt is a total savior. This one by Tommy Hilfiger will ensure that your figure isn't lost in a sea of breezy cotton and its classic red cloth and leather combo would look smart with all your neutral pieces! All in all, we think this is one accessory that's too good to pass up, so you better get one before it's too late.--Erin Fitzpatrick