10 Preppy Summer Outfits That You Need in Your Wardrobe (Now!)ment

The weather is warming up and we’re all looking forward to the end of stay-at-home orders so we can get out and socialize. When you can finally get back out in the world again, you’ll want to make sure you look great!

If you want to be a well-dressed guy, you need to start with a closet that’s well-stocked with all the basics you’ll need. This way, you can easily mix and match to create stylish outfits without too much effort.

Now is the perfect time to start planning out your preppy summer outfits! Check out these recommendations for all the pieces you need to have readily available.

Preppy Pants and Shorts

Pants are the foundation of every outfit. While they're often considered a neutral, you can have fun with summer bottoms in brighter colors and prints! Plaid and Houndstooth are the prep staple in the winter months, but the summertime is really when the true prep shines!

Khakis or Chinos

Want to make sure you always have something to wear to every event? You'll need at least two pairs of khaki-colored slacks, one that is more formal and another pair that are casual. Make sure they fit you well! This pant will be the workhorse of your wardrobe, pairing back with all sweaters, polos, loafers you put with. The style is ivy-inspired, and a clean classic look. 

Medium-Wash Jeans

Do everyone a favor and get rid of those faded blue-colored jeans you’ve had since the ’90s. Instead, pick up a pair of darker, medium-washed jeans. This will give you a much more put-together look while still being comfortable. This casual-cool look is great for after work drinks and casual Saturday night dinners on the town. Make sure you get a slimmer leg style to look more modern and well-fitting. This will help to elevate the basic blue jean to the polished prep level. 

Khaki and Navy Shorts

Solid colored shorts that come about two to three inches above your knee are another must-have staple for casual summer outfits. Just the right length for maximum movement to jump from dock to boat, but long enough to not get looks in the Clubhouse. You’ll want khaki and navy at a minimum, but feel free to add some more colored shorts as well! May we suggest a bubble gum pink, sky blue, grass green or buttery yellow. All classic prep staples, and sure to spark joy. 

Shorts With Small Patterns

Shorts embroidered with tiny patterns, from flamingos or pineapples to sailboats and anchors, are all the rage right now! They also have their roots in traditional, age old Preppy style. A classic seersucker material has also been a preppy staple for decades. These shorts should fit the same as the solid-colored ones described above. Seersucker is lightweight and breathable, slightly puckered fabric, and perfect for packing for the Island getaway. 

Preppy Shirts

Once you have your pants and shorts under control, you can start to have some fun with a variety of shirts in different styles and patterns. Remember, the summer is the time to really go wild with color and pattern!


Even in the summer, the standard button-down shirt is a necessity! You’re sure to have some formal occasions to attend and these will pair perfectly with all khakis, colored shorts, or jeans. Choose a lighter material so you don’t get too sweaty and stick with a mix of colors—think white, pastels, and bright plaids. Seersucker also comes in top versions, as well as the Madras Patchwork. Both fabrics are quintessential aesthetics of prepdom, and you can never go wrong. 

Casual Polos

Collared polo shirts are the perfect compromise for semi-casual occasions. Choose a light material and the same fun, bright colors mentioned above. This style is ideal for a casual work Friday or hitting the links on Saturday. Nowadays, performance fabric Polos are all the rage. With their moisture-wicking properties, stretch fabrics, and easy care, the Performance Polo certainly has its place in the summer wardrobe. Of course, the ever classic Pique Polo is still alive and well from traditional companies as well. 

Short-Sleeved Button-Downs 

This is a great place for you to have some fun! Choose a light, neutral color, and a few patterned shirts. Plaids are a great option, as are fun patterns like the ones you choose for your shorts (just don’t wear them together!). When choosing your material, opt for cotton, linen, or blends. These will be light weight, keeping you looking and feeling cool. 

Nice White T-Shirts

You can dress down a button-up by leaving it unbuttoned or only half-way buttoned, but to do this, you must have a t-shirt under it. And not that ragged old college tee you wear for pick up basketball! Keep a few nice white t-shirts on hand for just this purpose.


Lastly, you’ll need to pick up some accessories. This includes at least a couple of pairs of casual shoes, trendy socks, and one or two casual belts. A light straw fedora, or sharp baseball cap are also cool summer essentials, that still allow you to show off your personal style.

There you go, you now have your closet perfectly prepped!

The Best Preppy Summer Outfit Ideas

Not sure how to put all these clothing items together? Keep reading for our most inspiring ideas.

Short Sleeves and Shorts

When it’s too hot for sleeves, a lightweight short-sleeved shirt with a plaid pattern pairs perfectly with a pair of navy-blue shorts. Add a pair of super-clean white sneakers for a look that gives off a decidedly cool and relaxed vibe. Perfect for days walking around town and heading to lunch. 

The Preppy Casual Look

Need to dress up but want to stay cool? Shorts aren’t only for the beach! Pair your khaki shorts with a button-down shirt with the sleeves rolled partway up. Or throw on a Madras Patchwork Short and tuck in a short sleeve Linen Shirt. 

Accessories are critical for this outfit, so make sure you add a belt, watch, and a pair of sunglasses. Toss on a pair of loafers and you’re ready to take on the town!

Low-Contrast Colors

For a super-casual but still-put-together look, pair a well-fitting yellow t-shirt with a pair of khaki shorts and white sneakers. Since this outfit is completely comprised of low-contrast colors it works perfectly for those hot summer days.

Unbuttoned Button-Up

For this look, start with a pair of khakis or chinos and a white t-shirt. Add a denim button-up shirt, but leave it completely unbuttoned. Finally, add a pair of suede loafers and some trendy shades.

Elevated Denim

Denim shirts can get a lot of wear in the summertime. Simply buttoning it up gives it a dressier look. Pair it with your chinos and your favorite loafers.

Don’t forget to finish off your outfit by rolling up your sleeves, adding a stylish watch, and grabbing your shades on your way out the door.

Summer Stripes

A striped polo shirt paired with pastel colored shorts and white sneakers gives you a sporty, comfortable look. Make sure you’re prepared for cooler nights by grabbing a classic crew neck sweater or ¼ zip pullover. This will complement your outfit and keep you toasty all night long.

Colorful Business Casual

Who says business casual needs to be boring? Choose a pair of lightweight chinos and pair them with a brightly colored and/or patterned button-down shirt (make sure it fits you right!). A pair of stylish brown leather bit drivers will perfectly complement this outfit and pull everything together.

Shop for Your Preppy Summer Outfits Today!

At Castaway Nantucket, we pride ourselves on staying at the cutting edge of preppy style and we have everything you need to create unique and stylish preppy summer outfits.

Browse through our newest arrivals today so you can show off your new style this summer!

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