8+ CUTE Summer Preppy Outfits

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With summer quickly approaching, I am putting together a ton of summer preppy outfits that will help us stay chic during the hot months.

bermuda shorts outfit

My most default style in life is preppy because of years of private school. I have ventured out of the preppy style to try different styles, but my default is prep. I am so excited to share with you some summer preppy outfit ideas.

Summer preppy outfits are classic, clean, and crisp. They are not necessarily trendy outfits, but they can go in and out of mainstream style, but preppy style really never falls out of favor. It’s classic!

Preppy by definition comes from kids going private prep schools. You can certainly dress preppy without ever having to gone to a private school. It is a style like any other.

In certain situation, preppy clothes are the norm. Going to a polo match or a garden party or the Honda Classic.

I could live in a world filled with gingham and seersucker and be happy forever.

Summer Preppy Outfits

Monogram Jewelry

One of the most preppy things to do is Monogram. You can wear monogram necklaces with your own initials or your children’s initials.

I found this brand Rellery that does an amazing job of monograming in a stylish way. I have the triple mini disk necklace with my initials. It looks great on its own or layered with other necklaces.

Preppy Jewelry

For jewelry, I like to keep it simple and understated. These beautiful bracelets are understated and monogram! They are perfect for a stylish everyday preppy look.

I put my daughter’s name on the Double Heart Bracelet With Bead Chain. It is very preppy and she loved seeing her name on my wrist!

I also got the Checker Heart – Initial Bracelet to wear with the heart bracelet to make a stylish bracelet stack.

All Rellery’s pieces are ethically sourced and produced skilled artisans mostly in their U.S studio.

Rellery Jewelry

Preppy Staple Pieces

You have to consider the place that preppy people frequent. Think tennis, polo, golf, and squash matches to name a few preppy sporting events. Also, sail boating is very preppy.

One of my favorite summer preppy staple is this white blazer. Here are 10+ White Blazer Outfits.

White Blazer and Jeans

Preppy Bottoms

You can begin your preppy outfits with preppy bottoms like khakis, classic denim, or a nice pleated midi skirt. The classic preppy look has lots of classic colors like light pink, light blue, navy, and white.

Summer Preppy Outfits

White Jeans

My favorite preppy bottom is a pair of nice white jeans that are not skin tight and hefty enough that you cannot see through them. My favorite pairs are from J.Crew and J.Brand.

You can get a pair of skinny jeans, straight leg, or even mom jeans in white.

White Jeans Preppy Bottoms

Preppy Shorts

Solid colored shorts in navy or white are a staple for casual summer preppy outfit. You want them to be long enough that they are conservative and cover your bottom well.

Preppy shorts outfits

Bermuda shorts and 5 inch shorts are both great choices for preppy short lengths. I was excited to see that the Bermuda shorts are one of this years big fashion trends! That makes them much easier to find! YAY!

bermuda shorts outfit

Navy, white, and light denim (minimal if any distressing) are staples, but you can also add a bubble gum pink or sky blue to your preppy outfits.

These Lilly shorts can also look preppy when paired with a navy polo or navy top.

Preppy Tops

In the summer a classic preppy look is done with a short sleeve t-shirts that lays nicely and does not look slouchy or wrinkles. This is one of my favorite preppy t-shirt. It fits great and I have it several colors – navy, black, and white.

Button down shirts are a great choice for summer. You can wear long sleeve and roll them up in the summer with shorts or tucked into a skirt.

With the AC cranking in most places, having a cardigan tied on your shoulders is a great way to be ready for the changes from indoor to outdoors.


Nothing says preppy like a nice polo shirt for men or women. My favorite preppy brands for polos are Ralph Lauren, Lacoste, J.Crew, and Burberry.

Wearing a popped color is very preppy practice too. Personally, I always want to fix their people’s collar, but it is definitely a trend in preppy circles for both men and women.

Preppy Prints

There are so many fun prints to get a preppy look. My favorite preppy prints are seersucker, navy stripes, plaid, gingham, and Lilly Pulitzer colorful prints.

Lilly Preppy Outfit


One of my favorite preppy fabrics is seersucker. It is perfect for spring and summer.


Another awesome preppy print is gingham. It is very summery and light weight. You can wear gingham dresses, shorts, shirts, and even blazers in the summertime.

During the summer, wearing Lilly prints is very preppy. I think of Jackie O looking very preppy with her bright colors Lilly shift dresses and white sunglasses.

Sail boat prints and lobster prints are very preppy too.

Preppy Summer Dresses

You can wear a preppy dress to make casual summer outfits. They are simple to throw on and go.

Preppy Summer Dresses

Preppy Shoes

Top off your summer preppy outfits with preppy shoes like boat shoes, preppy sneakers, and sandals in the summer time.

Lilly Preppy Dress

Sperry Preppy Shoes

You can get super cute preppy shoes from Sperrys like boat shoes and slip on sneakers. I absolutely love Crest Vibe sneakers from Sperry and have them in several colors – white, navy, and light pink.

Jack Rogers

Another preppy brand that I love is Jack Rogers. The make jack sandals that go so well with preppy summer outfits. I have jacks in platinum, black and camel.

The platinum are my most worn to date because they are a very neutral metallic that matches both gold and silver.

If you want to personalize your jacks, you can get them monogramed.

Loafers & Mules are a great choice for preppy classic footwear.

Preppy Accessories

Headbands, hats, and sunglasses are common preppy accessory for women.

These headbands from Twice the Dreams are a great choice to keep your hair off your face in summer. They have some in preppy summer prints like gingham and seersucker.

One of the top preppy brands for sunglasses are from Ray Ban. The classic wayfairer and aviator styles are super preppy.

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