13 Cute Preppy Outfits for School: Preppy style at school is like peanut butter and jelly. It just fits.

It’s clean. It’s classic.

And honestly, it’s way easier to pull off than you might think.

You don’t have to live in a movie set at a fancy private academy to rock preppy outfits. You just need the right pieces and a little bit of that “I care but not too much” attitude.

Here’s 13 preppy outfit ideas you can steal, remix, and make totally your own.

13 Cute Preppy Outfits for School:

1. Polo Shirt + Pleated Skirt

Let’s just start with a classic.

Polo shirts are basically the MVP of preppy dressing.
Tuck one into a pleated skirt, and boom you’ve got the ultimate school outfit.

Best color combos?

• White polo + navy skirt.
• Light pink polo + gray skirt.

Slip on white sneakers or loafers, and toss your hair into a loose ponytail if you want the full effect.

One of my friends wore this combo every Friday. People legit thought she had her life together because of it. (She didn’t. But she looked like she did, and that’s half the battle.)

2. Sweater Vest + Button-Up Shirt

Nothing screams “smart and stylish” louder than a sweater vest layered over a crisp button-up.

• Go neutral: white shirt + beige vest.
• Go bold: light blue shirt + patterned vest.

Top it off with tailored jeans or a plaid skirt.
It’s like you stepped straight out of a 90s yearbook photo… but cooler.

Pro tip: Add chunky loafers for major style points.

3. Cardigan + A-Line Dress

You want cozy? But still put-together?
Meet your new best friends: cardigans and A-line dresses.

Throw a fitted cardigan over a simple dress. Button just the top few buttons. Let the bottom flap open. Magic.

Color inspo: Try a navy dress with a white or soft yellow cardigan. It feels so classic it hurts.

Honestly, I wore this combo to my 8th-grade graduation practice and felt like the main character in a teen movie. Still think about it.

4. Rugby Shirt + Skinny Jeans

Hear me out.

Rugby shirts are underrated. They’re a little sporty. A little serious. A lot preppy.

Pair a striped rugby shirt with dark skinny jeans. Push the sleeves up just a bit.

Add low-top sneakers, and suddenly, you look like you belong on some Ivy League campus tour.

Best part? They’re so comfy, you’ll forget you’re even trying.

5. Blazer + Graphic Tee

Blazers aren’t just for job interviews and debate team anymore.

Throw a slightly oversized blazer over a casual graphic tee.
It’s messy preppy perfection.

Tuck the tee into high-waisted jeans or a mini skirt. Add sneakers to keep it chill, or loafers if you’re feeling fancy.

The contrast of casual and polished makes it even better. It says, “Yeah, I know what I’m doing.”

6. Tennis Skirt + Crewneck Sweatshirt

If you’re not ready to give up comfort for style, you don’t have to.

Pair a tennis skirt with a slightly oversized crewneck sweatshirt.

Color ideas:

• White skirt + navy sweatshirt.
• Plaid skirt + cream sweatshirt.

Slide on some white sneakers or even Mary Janes with cute socks. Done and done.

My bestie used this as her go-to “I’m running late but still wanna look adorable” outfit. And honestly? It never failed.

7. Button-Down Shirt Dress + Belt

Want to look polished but not stuffy? Wear a button-down shirt dress.

Cinch it at the waist with a belt. Throw on ballet flats or low-heeled boots. Top it off with a crossbody bag.

You’ll look like you just got back from a weekend at Cape Cod. Even if your actual weekend was just Netflix and leftover pizza.

8. Cable Knit Sweater + Chinos

Channel all the classic New England fall vibes.

A thick, cozy cable knit sweater over a pair of fitted chino pants is pure prep heaven.

Colors that never miss:

• Navy and khaki.
• Cream and olive green.
• Maroon and gray.

It’s like sipping apple cider but with your outfit.

Small detail: A tiny gold necklace or a vintage watch finishes this off perfectly.

9. School Sweater + Plaid Skirt

Nothing feels more school-ready than a varsity or letterman-style school sweater paired with a plaid skirt.

Tuck in the front a little.
Wear white sneakers or saddle shoes if you really want to lean in.

Honestly, there’s something about a plaid skirt that just feels right in a school hallway. Like you’re ready to pass notes or ace a test or both.

10. Preppy Tracksuit (Trust Me)

This one might surprise you.

Preppy doesn’t have to mean stuffy blazers all the time. A matching tracksuit think fitted joggers and a zip-up jacket can still feel preppy if you pick classic colors like navy, gray, or burgundy.

Wear a collared shirt under the jacket for an extra touch. It’s sporty, but polished.

In other words: Varsity tennis team captain energy.

11. Denim Skirt + Long Sleeve Polo

Denim skirts aren’t just for festivals. Paired with a long sleeve polo shirt?

Chef’s kiss.

Wear mid-length denim (not too short, not too long) and a fitted or slightly oversized polo tucked in.

Top it off with some gold hoop earrings and low-top sneakers or loafers. It’s casual prep at its best.

Bonus: Add a tote bag with a sassy quote for a little personality punch.

12. Striped Sweater + Khaki Shorts

For warmer months (or just overheated classrooms), you can still stay preppy without layering yourself into oblivion.

Wear a striped sweater with khaki shorts. Choose sailor-style wide stripes if you can. It feels a little nautical very “summer in Nantucket.”

Simple sneakers or boat shoes tie it all together.

13. Peter Pan Collar Blouse + Suspender Skirt

Feeling extra cute?

A Peter Pan collar blouse with a suspender skirt is basically preppy Disney princess vibes.

• Soft pastel colors.
• Tidy, small prints like polka dots or gingham.
• Simple flats or Mary Janes.

You’ll look adorable without going overboard.

And yes, the suspender straps will make you feel unstoppable. You’ve been warned.

Final Thoughts: 13 Cute Preppy Outfits for School!

13 Cute Preppy Outfits for School! Preppy style isn’t about dressing like someone else. It’s about using those timeless pieces polos, pleats, loafers and giving them your own twist.

Some days you’ll feel like rocking the full button-up-blazer look.
Other days, you’ll toss on a tennis skirt and sweatshirt and call it a day.

Both are perfect.

The trick is to feel good in what you’re wearing. Because confidence? It’s the best accessory you’ll ever own.