Preppy-Inspired Outfits & Other Trendy Cute Pieces Getting Insanely Popular On Amazon

This tennis dress is made from ultra-soft, sports-ready fabric that is not see-through and absorbs moisture, ensuring that you stay comfortable whether you're on the court or out and about. It also comes with separate matching shorts for added coverage and flexibility — these have two large side pockets which can hold everything from an iPhone to a tennis ball.

• Available sizes: X-Small — XX-Large
• Available colors: 15

This Hanes polo shirt is made from a high-quality, moisture-wicking jersey knit to help you remain cool and comfy. It features a classic three-button placket and welt collar for a polished look. Enjoy a close-but-contoured fit or size up for a more relaxed look.

• Available sizes: Small — 3X-Large
• Available colors: 7

Crafted from a stretchy and breathable viscose blend, this super-soft cardigan makes a lightweight and cozy layer for any preppy look. With long sleeves, a button-down front, ribbed hemline and sleeve cuffs, its got a classic look that’s always in style. This casual cardigan pairs effortlessly with camisoles, dresses, jeans, and more.

• Available sizes: Small — XX-Large
• Available colors: 32

Step up your prep style with these trendy platform sneakers. Wearable in any season, these versatile sneakers are made from high-quality canvas and have an easy-wearing platform that’s just over 1 inch tall. The sleek and comfortable design makes them ideal for pairing effortlessly with any casual look for a fashionably preppy accent.

• Available sizes: 5 — 11
• Available colors: 2

Designed for optimal performance, these compression socks feature varying levels of targeted compression to enhance speed and mobility. Crafted from a durable and flexible nylon blend, they offer exceptional comfort and support. Available in various color options, they add a cute touch to your preppy look while also helping boost your athletic prowess.

• Available sizes: Small-Medium — Large-X-Large
• Available colors: 35+

With a 4.5-star rating after more than 85,000 shoppers have weighed in, you know this flared mini skirt is worth an immediate ‘add to cart.’ Crafted from a lightly textured fabric infused with spandex for stretch, and topped with an elastic waistband, it offers an always-comfortable fit and that preppy aesthetic. Its versatile design makes it ideal for pairing with nearly any top, for everything from casual errands to dates and parties.

• Available sizes: X-Small — XX-Large
• Available colors: 20

This lightweight crochet knit cardigan is forever chic with its loose fit and long batwing sleeves, while the crochet detailing infuses an old money touch. The open front, shawl collar, and draped hem offer an elevated dose of casual charm. Available in an array of colors, it’s a polished yet breezy go-to.

• Available sizes: X-Small — 3X-Large
• Available colors: 28

With a trendy high waist and ultra-wide legs, these Bermuda shorts also have that classic longer length that falls just above the knee. The greater coverage, smart-looking pleats, and belt loops to highlight your favorite chic leather belt, all work together to bring an elevated touch to casual looks.

• Available sizes: X-Small — 3X-Large
• Available colors:

This chic two-piece lounge set is made of an ultra-soft cotton-blend knit with luxurious ribbing, and is perfect for a coordinated look with zero stress. Featuring an oversize sweater with a scoop neck and fashionable dolman sleeves, with pull-on ribbed shorts, this preppy set does double duty if you wear it as separates. Choose from colors ranging from muted neutrals to statement-making brights.

• Available sizes: Small — X-Large
• Available colors: 30

These aviators not only exude vintage charm, from the tortoiseshell frames to the double-bridge design, but also tend to suit a wide range of face shapes. Crafted from premium materials, including UV400 lenses and sturdy metal hinges, these sunglasses provide superior glare reduction and UV protection, and long-lasting durability for everyday wear.

• Available sizes: One Size
• Available colors: 17

Take your wardrobe in a country-club direction with this stylish short sleeve sweater top with a polo collar. Featuring a classic V-neck with a ribbed trim and timeless cable knit detailing, this top is perfect for transitional seasons or warmer weather. Crafted from a lightweight, sweat-absorbing viscose blend, it offers a close but comfortable fit.

• Available sizes: Small — X-Large
• Available colors: 4

This partially pleated athletic skirt is ideal for actually working out or achieving a polished athleisure look. It features a sleek A-line silhouette, a fluttery hem, and a high waist and wide waistband for top-tier comfort. With three mesh-lined pockets to secure all your essentials and anti-slip strips on the inner shorts to hold them in place, it’s the perfect piece to stay sporty and secure.

• Available sizes: X-Small — XX-Large
• Available colors: 15

Style up your preppy-inspired outfit with these chunky sneakers, featuring a breathable mesh and PU upper that looks much higher-end than this price tag. A cushioned sponge insole and lightweight, nonslip outsole ensure comfort and a sure step. Boasting a 2.4-inch chunky sole, these sneakers add a stylish height boost, complementing everything from mini skirts to leggings.

• Available sizes: 6 — 11
• Available colors: 5

Step your accessory game up with these stackable beaded bracelets, featuring a vibrant mix of colorful vinyl disc beads. Designed with a stretchy band, they comfortably adapt to most wrist sizes. Choose from a rainbow of colorful options to add a pop of liveliness to your look (or hand them out at your next Taylor concert).

• Available sizes: One Size
• Available colors: 20

This skater skirt features a highly stretchy elastic waistband designed not to pinch, but stay securely in place. Designed with a lengthened cut to ensure coverage when bending over, this flowy skirt presents a chic A-line silhouette that pairs nicely with everything from button-downs to bodysuits.

• Available sizes: Large Plus — 1XL
• Available colors: 11

This bubble letter necklace features a unique 3D balloon design and a shiny gold finish. With an adjustable 16.5-inch chain, you can customize the fit to your liking. Crafted from durable brass plated in quality 18-karat gold, this hypoallergenic necklace is a perfectly preppy staple to add to your jewelry collection.

• Available sizes: One Size
• Available styles: 26

This casual zip-up sweatshirt is ideal for a relaxed, stylish look. It’s crafted from a plush, skin-friendly cotton blend and features classic ribbed cuffs complete with thumbhole cutouts, and a fleece-lined kangaroo pocket for added warmth. With its cropped cut and statement zipper, it offers laid-back appeal with a solid dose of style.

• Available sizes: Small — XX-Large
• Available colors: 17

This athletic dress is designed for both fashion and function. Featuring built-in shorts, a shelf bra with soft molded cups, and wide straps you can adjust for a custom fit, it ensures optimal support whether you’re playing your fourth tennis round or lounging at home. Made from stretchy, moisture wicking fabric, it transitions seamlessly from the gym to daily wear.

• Available sizes: 16 Plus — 28 Plus
• Available colors: 8

Elevate your preppy look — literally — with these platform sneakers. Combining cute textured corduroy uppers with contrasting rubber soles just over an inch high, they add a casual twist to any outfit while offering an added bit of height. Colors range from sea green to butter yellow to baby pink — and of course, classic black.

• Available sizes: 5 — 11
• Available colors: 7

These striped crew socks have a perfectly nostalgic ‘70s and ‘80s vibe. Each pair features classic stripes in a range of outfit-complementing colors. Made with breathable cotton and a cushy, tightly knitted yarn, these socks offer a soft, stretchy fit and all-day comfort, along with elastic cuffs that are designed to stay up without being too tight. With five in a pack, they’re also an incredible bargain.

• Available sizes: One Size
• Available colors: 11

This adjustable cap by adidas combines sustainability with performance, as it’s crafted from recycled materials to reduce plastic waste. Featuring the iconic adidas logo, it offers superior airflow and moisture-wicking through side-panel perforations. With UPF 50 sun protection and an adjustable hook-and-loop closure, it ensures a comfortable, customized fit while safeguarding you from harmful UV rays.

• Available sizes: One Size
• Available colors: 3

Elevate your wardrobe with ease by opting for this elegant two-piece set. The sleeveless vest boasts a deep V-neck, functional buttons, and a stylish W-shaped hem, while the shorts offer a comfortable elastic waistband and functional side pockets. Available in a range of colors, this set can be styled together or separately for both casual days and special outings.

• Available sizes: X-Small — XX-Large
• Available colors: 13

This oversize tee has statement-making color blocks reminiscent of your favorite rugby shirt, but with a comfy crew neckline. Made from a stretchy cotton-spandex blend, it’s got a supremely relaxed fit in a tunic length that’s ideal for sleeping, lounging, or a laid-back, dressed-down look. Choose from neutrals, brights, pastels, and fully striped versions.

• Available sizes: Small — XX-Large
• Available colors: 17

Make a statement with these unique sheer socks that feature a range of charming patterns within the five-pack. Made from delicate yet durable mesh, they add a stylish touch to your look whether you’re wearing penny loafers or chunky sneakers. They have an impressive 4.6-star overall rating, and many reviewers call out how fab they look with patent leather.

• Available sizes: One Size
• Available colors: 4

This fluttery skort blends ultra-mini style with athletics-ready function thanks to the built-in mesh shorts with dual pockets, a back zipper pocket, and additional hidden pockets in the waistband to house your essentials. Available in a variety of vibrant colors, the more statement-making options include neon green and even leopard print.

• Available sizes: XX-Small — XX-Large
• Available colors: 25

Level up your footwear collection with these iconic penny loafers. Crafted from high-quality faux leather with a sleek, ultra-polished shine, these loafers are ideal for dressing up or down and add a refined touch to any outfit. Chunky lug outsoles are on-trend while also providing a stable step.

• Available sizes: 6 — 11
• Available colors: 4

With its classic stripes and eye-catching gold buttons, this cardigan is giving nautical-chic. It’s made of a midweight viscose blend, and has two front patch pockets for added style and practicality. It also has an impressive 4.5-star rating after nearly 1,000 reviewers weighed in, with many of them calling out how it looks and feels like a much higher-end item.

• Available sizes: X-Small — X-Large
• Available colors: 13

Luxurious quilting, a strap with gold chain detailing, and a fun faux-leather tassel combine to give this crossbody bag an ultra-luxurious feel. The strap is adjustable so you can get your perfect crossbody drop, and it comes in a rainbow of colors from brights to pastels and jewel tones.

• Available sizes: One Size
• Available colors: 25

Constructed with an open-weave knit that’s breathable and breezy, this cardigan is a lightweight layer that’s a go-everywhere piece. The longer-length hem makes it ideal for pairing with everything from mini skirts to leggings, and its relaxed fit ensures you’ll feel comfy all day long.

• Available sizes: 16 Plus — 24 Plus
• Available colors: 15

This classic fleece vest is made with a brushed finish that’s oh-so-soft — the high collar was made for popping, and will feel delightfully cozy against your skin. The fleece is midweight so will add a layer of warmth and insulation without being over the top.

• Available sizes: X-Small — 6X-Large
• Available colors: 16

This highly rated pair of oversize sunnies — they boast an impressive 4.6 stars overall — is quickly becoming one of the most popular pairs on Amazon. With a UV400 rating, they’ll protect your eyes from UVA and UVB rays as the mirrored lenses give you a perfectly preppy vibe (though nonmirrored and cool gradient options are also available). The flat-front design adds a bit of futuristic edge.

• Available sizes: One Size
• Available colors: 9

Delivering a hint of ‘90s grunge with neon details that channel pure Y2K, this oversize sweatshirt is an exercise in contrasts — that looks cool no matter how you style it. It adds a laid-back touch to a pleated skirt and knee-highs, though can easily go full grunge by pairing with distressed denim.

• Available sizes: Small — 3X-Large
• Available colors: 16

Channeling the short length and pleats of a traditional tennis skirt — but in a shorts form that sidesteps windy-day wardrobe malfunctions — these running shorts bring the best of both worlds. They’re made from a quick-dry fabric infused with a touch of spandex for stretch, helping you stay cool and comfy whether you’re serving a tennis ball or serving looks.

• Available sizes: Small — X-Large
• Available colors: 13

Take your favorite T-shirt but make it fashion, and you’ll wind up with this cap-sleeve top. It’s made of a fabric blend with cotton for softness and spandex for light stretch. The relaxed fit and wide arm holes ensure it’s comfy and breezy as you pair it with everything from gym shorts to office-ready trousers.

• Available sizes: Small — X-Large
• Available colors: 21

Give your black jeans a break and slip these cute corduroy pants into the rotation. They’re made of 100% cotton for a soft, durable construction, and have traditional five-pocket styling and a straight-leg cut that’s perfectly on trend. Opt for this classic black or the pair in a warm camel color.

• Available sizes: 0 — 13
• Available colors: 2

Blending the sophistication of a sweater vest with the relaxed feel of a casual top, this sleeveless sweater hits all the marks. It’s made of an ultra-soft viscose blend with an oversize fit that ensures comfort while looking oh-so-stylish. The deep V-neck is also perfect for showing off preppy layered necklaces or a statement pendant.

• Available sizes: Small — XX-Large
• Available colors: 20

Made from a soft cotton blend infused with stretch, these denim shorts are as comfy as they are stylish. The high waist makes them easy to pair with everything from a tucked-in button-down to a cropped cami, while the button fly and oversize patch pockets add practical and fashionable detail.

• Available sizes: 6 — 16
• Available colors: 6

A wardrobe MVP you’ll likely reach for again and again, this woven belt is here to top off your fave khakis or cinch up a flowy dress for a sophisticated silhouette. Made of durable faux leather with an ultra-classic look, the golden O-ring buckle adds a subtly statement-making detail.

• Available sizes: One size (23 - 42 inches)
• Available colors: 4

Made of soft and breezy cotton with a linen texture, this two-piece set offers a sophisticated, put-together look without having to worry about coordinating. The shorts feature a high waist with comfortable elastic and a drawstring, while the button-down top has a slightly relaxed fit and roll-up sleeves. They naturally work well together, but can be styled separately for double the looks.

• Available sizes: 16-Plus — 24-Plus
• Available colors: 11

With three in textured velvet and three in velvet embossed with pearls, this set of six headbands is a simple way to add instant polish — and solid hair-wrangling — to your look. They have a nonslip design to keep them securely in place, and wrapped ends for comfy wear.

• Available sizes: One size
• Available colors: 7

Featuring a coquette bow and trendy colorways, this mini faux leather backpack feels perfectly of-the-moment. Despite its compact size, there’s still plenty of room to stash your iPad, phone, wallet, and more. Plus, the two side pockets make it easy to carry a water bottle and umbrella.

• Available sizes: One size
• Available colors: 18

With nine pairs included in a set, you’ll get a ton of wear out of these Y2K-inspired earrings. Choose from lightning bolts, smiley faces, hearts, and stars — all in an array of poppy colors — for dialing up the retro vibe of your look. They’re also fun to layer in an ear stack.

• Available sizes: 1
• Available colors: 1 multipack

What could be cozier than an oversize knit pullover with batwing sleeves? This version is rendered in the softest ribbed knit, with a split hem for wearing loose or French tucked in. The striped pattern featured here is a neutral MVP, but there are also poppy-bright options on offer for leaning into an ‘80s aesthetic.

• Available sizes: X-small – X-Large
• Available colors: 14

Head scarves are trending as the accessory du jour, and this crochet beanie captures the same vibe without the hassle of having to tie and retie. The cotton construction is soft and durable, and the slouchy fit keeps things comfy. Channel everything from a cottagecore vibe to a hippie-chic aesthetic with this affordable beanie.

• Available sizes: Medium — Large
• Available colors: 40

For the perfect extra layer, this puffer vest adds so much style and warmth. The chic stand collar, roomy side pockets, and cozy-without-being-bulky fit are all reasons to make this an immediate wardrobe staple. Choose from more than a dozen wearable hues, including some lovely pastel picks.

• Available sizes: X-Small — X-Large
• Available colors: 13

Featuring a quarter-zip collar, drop sleeves, and a slouchy fit, this oversize sweatshirt is so cozy. The longer hem makes it perfect for leggings days, and the cotton blend keeps things breathable. Wear it for a comfy off-duty lounge look or throw it on over your tennis dress for a preppy, sporty vibe.

• Available sizes: Small — XX-Large
• Available colors: 27

Crafted from a buttery-soft stretch fabric, these biker shorts are perfect for everyday wear and workouts alike. They come with a high waist and are offered in two inseam lengths — 5 inches and 8 inches — for the perfect fit. Choose from options with pockets and without.

• Available sizes: Small — X-Large Plus
• Available colors: 2

The preppy tennis aesthetic isn’t going anywhere, and this athletic dress is acing the trend. The cutout at the center adds a little spice, while keeping things breathable, and it’s echoed in the back for a cohesive look. The high-stretch fabric is designed to move with you, and the built-in shelf bra and shorts (with pockets) are court-ready.

• Available sizes: Small — XX-Large
• Available colors: 5

With a single-breasted button-down front and a flat collar, this shirt is giving menswear pajamas — perfect for nailing the PJs as outerwear trend. The statement prints range from animal to celestial, and the hem length is perfect for wearing loose or tucked.

• Available sizes: X-Small — XX-Large
• Available colors: 26

Lounge in style with this two-piece waffle-knit set. The oversize button-down top is great worn open over a bralette or tank, or you can button it fully for more coverage. The pull-on shorts have pockets for a practical touch and a polished cuffed hem to dress things up enough for errand runs and coffee breaks.

• Available sizes: Small — XX-Large
• Available colors: 10