preppy summer outfits

11 Ways to Style Cute Preppy Summer Outfits

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Summer is the perfect time to bring your country club Pinterest board to life and try out a preppy style. Button-down shirts, tennis skirts, and stripes – what’s not to love? Preppy summer outfits are timeless and classic and can easily be dressed up or down, whether you’re going boating or out to lunch. If you’re looking for some inspiration this season, check out these 11 ideas for styling your preppy summer outfits. Whether you’re headed to a party, a picnic, or just out shopping, these ideas will bring out the preppy side in you!

1. white button-down + denim skirt + loafers + belt

There are many different styles under the preppy umbrella, whether that’s Ralph Lauren prep school chic or à la Reese Witherspoon and bright colors. For a look that leans more classic style, consider copying this easy look of a white button-down shirt and denim skirt. It doesn’t need much, but adding a belt to your outfit is one of the best ways to complete your look. Plus, belts are also a great way to add some extra flair to your preppy staples!

preppy summer outfits

button-down | skirt | loafers | belt

2. seersucker shorts + polo shirt + boat shoes + denim jacket + oversized pearl earrings

We can’t talk about preppy outfits without mentioning polo shirts, seersucker shorts, and boat shoes! This outfit encapsulates a certain style of prep personality and would be cute for a day spent outdoors or on the water.

preppy summer outfit

shorts (similar) | top | shoes | earrings | jacket

3. striped button-down + cotton shorts + loafers + tote bag

If you’re looking for something more casual, opt for solid-colored shorts instead of a denim skirt. Tailored shorts paired with a button-down shirt (especially blue and striped) are a knockout combo for a preppy look.

preppy summer outfits

button-down | shorts | loafers | tote bag

4. sundress + clogs + straw basket bag

For a stylish twist on a preppy look, pair a striped seersucker-inspired dress with a straw basket and clogs. End result? Picnic chic.

preppy summer outfits

sundress | clogs | basket bag

5. blue button-down + tennis skirt + cardigan + sneakers + visor

Not only is this outfit perfect for hot summer days but it embodies the preppy style seen at country clubs and other events. Baseball hats or visors make for the perfect finishing touch! Now you’re ready to hit the green.

preppy summer style

skirt | button-down | cardigan | visor | shoes | necklace

6. striped button-down + linen shorts + loafers + watch

Part prep, part European chic, this timeless look is a no-fail outfit combination for summer days. The pop of red stripes adds additional interest and style to this outfit.

preppy summer outfits

button-down | shorts | loafers | watch

Related: French Sole Alibi Sandals vs Hermès Oran Sandals | I’ve Had Both and These Are My Honest Thoughts on Them

7. shirt dress + loafers + belt

A cotton dress is a perfect thing to throw on when you want a stylish outfit without expelling a lot of effort. Once your dress is on, most of your outfit is already completed! Blue is a great summer color, but you can’t go wrong with a little white dress either.

preppy summer outfits

dress | loafers | belt

8. linen blazer + cami top + linen pants + loafers

This outfit choice may be on the fancier side of preppy summer outfits, but it’s still one worth saving for later. Both the blazer and pants have a relaxed silhouette, so though this is a matching suit set, it still feels approachable and comfortable for your day-to-day. Not to mention stylish!

preppy summer outfits

blazer | top | pants | loafers

9. striped cardigan + denim shorts + loafers + watch

If you’ve got a striped cardigan then you don’t need anything else. Okay, slight exaggeration, but the point is that this wardrobe piece is so timeless and versatile that it’s easily a must-have in your wardrobe. Pair your cardigan with shorts for a laid-back feel. Finish off the look with loafers and a leather watch to add that preppy touch.

preppy summer outfits

cardigan | shorts | loafers | watch

10. sweater + denim skirt + socks + sneakers

If your climate is more on the mild side or you like to wear long sleeves, then this is an outfit for you to copy. This sweater gives all the prepster vibes, as do the sneakers. Get some sunshine on your legs with a denim skirt. If you have an unusually chilly day, a trench coat would look great with this outfit too.

preppy summer outfits

sweater | skirt | socks | sneakers

11. striped cami + striped cardigan + skort + sneakers

When it comes to casual summer outfits that are effortlessly chic, you can’t go wrong with dressing up a skort. A matching striped cami and cardigan set instantly add that polished look, as do the sunglasses and bracelet. The sneakers bring the outfit back down to a casual aesthetic, encapsulating casual chic perfectly.

preppy summer outfits

cami | cardigan | skort | sneakers | bracelet

Preppy Staples and Preppy Brands

The preppy look is all about classic style. Want to get started with classic preppy staples? Polo shirts, chinos, button-down shirts, and boat shoes are all great options to build your preppy wardrobe with.

Staples like polo shirts and button-downs can be paired with solid-colored shorts or skirts for a great way to stay comfortable and stylish. A relaxed silhouette in a collared shirt is also a great choice for those who want to look polished but still keep it casual. Peter pan collars give a preppy look, though they are more of a fad lately.

Most preppy fashion showcases these pieces in pastel colors, though I believe neutrals are usually the way to go.

But if you like bright colors and fun prints, a lightweight Lilly Pulitzer dress is a great piece to have for vacations, parties, or formal occasions. Bright and patterned shorts are also a great way to add some pizzazz to your outfit.

Don’t forget to accessorize with a hat, watch, pair of statement sunglasses, or a tote bag for an extra touch of style and class.

Some of the top preppy brands include Ralph Lauren, Vineyard Vines, Lilly Pulitzer, and Jack Rogers.

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Whether you like neutral colors and button-down shirts or fun prints and patterned shorts, there are lots of great options for preppy summer outfits, so don’t be afraid to experiment and create a look that’s all your own. No matter what your personal style is, you can find the perfect preppy look to suit it!

To complete your summer outfits, you need a pair of sunglasses. Find out the trending styles in this next post: The Top 7 Sunglasses That Are in Style Right Now


Founder and editor of My Chic Obsession, Carolyn is your trusted fashion maven. Carolyn's drive to help others achieve a classic and timeless wardrobe fuels her posts, making a go-to resource for style seekers worldwide. Beyond the wardrobe, she resides in the heartland of the Midwest, dreaming up new ideas and raising her two lively boys - her biggest fashion critics.