Nautica’s identity as a coastal preppy brand has been consistent since the brand’s inception in the ’80s. The brand features lots of preppy styles such as striped blazers, shirts with sailboat graphics, and even classic polo dresses like this one here.
2
this sporty set
Recreational Habits Black Tee
Recreational Habits hopes to make preppy clothing accessible to everyone. They have fun activewear pieces like this tank (and matching skirt!) as well as sweet sweaters and dresses.
3
this iconic flag sweater
Ralph Lauren Flag Cotton Crewneck Sweater
Ralph Lauren is an OG. The brand has been around since the ’60s and has become a staple brand for classic preppy pieces like polo shirts, blazers, and of course, an American flag sweater. Just picture yourself on a beach this summer with this layer draped over your shoulders. Très chic!
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4
this boatneck top
J.Crew Boatneck Muscle T-shirt in Stripe Mariner Cotton
I’ve always considered J.Crew a 10/10, go-to brand. They have solid basic tees, jeans, sweaters, jewelry…you name it. Not only that, but J.Crew is also a great place to shop for preppy pieces. This boatneck muscle tee with blue and white stripes radiates a mature and elevated preppy girl look.
If you want to nail the preppy look this fall and winter, I’d highly recommend looking at pieces from LL Bean! The retailer has an outdoorsy vibe which is perfect for those who like to spend time in nature in the colder months of the year. Pair this Fair Isle sweater with your fave pair of jeans for a modern, casual get-up.
6
these standout sandals
Jack Rogers Lauren Mid Heel
You gotta have some on-theme shoes to go with the whole moment! Enter: These Jack Rogers heels. The iconic round medallion detailing is essential to Jack Rogers’ shoes and is an instantly recognizable feature within preppy fashion.
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7
this royally-loved vest
Barbour Kelley Quilted Vest
JSYK, Barbour is a widely known brand that even the English Royals wear! They make great outwear that is fundamental to a year-round preppy wardrobe. Consider this quilted vest a transitional piece to prep-ify your ‘fit.
8
this nautical sweater
Brooks Brothers Relaxed Linen Tennis Sweater
You may see the brand name Brooks Brothers and think of men’s suits. However, Brooks Brothers has some really great preppy pieces for women, like this gorgeous v-neck sweater with the classic white stripes around the neck and sleeve endings.
9
this essential linen dress
Lands’ End Women’s Linen Sleeveless Midi Dress
Lands’ End actually began as a company that sold sailboat equipment and then transitioned to apparel in the late 1970s. This nautical influence has taken over the style of the brand’s clothing, including this lightweight linen dress, which is the perfect piece to wear for a leisurely stroll in a coastal beach town.
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10
this chic midi skirt
Vineyard Vines Silky Slip Skirt
Now 41% Off
Credit: KATE LACEY
Vineyard Vines might be the first brand that comes to mind when you think of preppy style. They’ve seriously solidified their spot in this specific fashion market! This gorge slip skirt paired with a belted cardigan will still give you a preppy look while simultaneously making you look chic as ever.
11
this striped button-down
Old Navy Oversized Button-Down Boyfriend Shirt
Look, I understand that preppy clothes can sometimes come along with steep price tags. However, there are a lot of inexpensive brands that feature pieces that you can style in preppy ways such as this button-down from Old Navy! Pair it with white jeans and a thick headband for a classic preppy look.
12
this statement tank
Southern Tide Staci Active Ruffle Tank
Preppy clothing isn’t limited to fancy dresses or sweaters. Southern Tide makes great preppy activewear such as this tank with ruffled straps and this printed tennis skirt. This whole ‘fit is perfect for playing some pickleball with your fam!
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13
this sleek set
Lilly Pulitzer Shelli Stretch Top & Sarissa Stretch Short Set
Lilly Pulitzer has been one of my fave preppy brands since I was young. They carry the most quintessential preppy pieces—from seashell-printed maxi dresses to short sets like the one shown here, Lilly pieces will 100 percent give you the ~look~ you’re going for.
14
this scallop-trim dress
English Factory Contrast Scalloped Trim Cotton Midi Dress
English Factory offers several elevated basics and preppy pieces just like this dress. It features a scallop hemline which is a very common feature in preppy clothing!
15
this polished jacket
Ann Taylor The Short Patch Pocket Jacket in Confetti Fringe Tweed
Ann Taylor carries plenty of polished and sophisticated styles that can also give you a preppy look. How fab is the tweed and gold-button combo on this jacket?
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16
this gingham duo
Tommy Hilfiger Gingham Pull-On Seersucker Short
Tommy Hilfiger is another classic brand in this fashion realm. The brand started in the ’80s and features preppy staples like polo shirts, dresses, and blazers. This gingham blazer and shorts set can be worn together or separately to make you look preppy any day.
17
this quintessential preppy shoe
Sperry Authentic Original™ Boat Shoe
You must have a boat shoe to really lean into the trend. I don’t make the rules! But more specifically, Sperry Top-Siders. Sperry shoes were developed as boating shoes in the early 20th century and have transformed into one of the most well-known symbols of preppy fashion.
18
these versatile white shorts
Tuckernuck Milana Shorts
Tuckernuck is a retailer that carries lots of brands as well as clothing that they produce under their eponymous label. The brand name comes from the tiny island off the coast of Cape Cod, a town known for its preppy fashion. So go ahead and get yourself some Tuckernuck pieces like these classic white shorts that are perfect for a summer on a boat in the Cape. I can see the Instagram pictures already!
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19
this stunning two-piece silhouette
Eloquii Yarn Dye Striped Straight Leg Pant
Like a few of the brands on our list, Eloquii doesn’t outwardly present itself as a preppy brand. However, they have several pieces that radiate that vibe. Check out these striped straight-leg pants that could definitely enhance your preppy style, especially paired with the matching top!
20
this darling maxi skirt
Posse Harvey Skirt
During her wedding weekend last year, Sofia Richie Grainge wore a two-piece set from the elegant and classic brand Posse. This brand is the definition of sophisticated and subtle preppy vibes, IMO. Style this sleek white maxi skirt with a striped shirt for the ultimate quiet luxury look.