Ready to channel your inner Blair Waldorf? Preppy fashion is having a major moment, and it’s more than just tennis skirts and polo shirts! Whether heading to brunch, conquering the office, or wanting to elevate your everyday style, these 30+ preppy outfits blend classic sophistication with modern flair.
From pleated mini skirts paired with oversized blazers, and crisp button-downs under cable knit sweaters that scream “old money aesthetic,” these looks are about to make you the best-dressed person in any room!
1. Long Sleeve Cropped Sweater and Plaid Skirt
Preppy outfits in tan and brown shades such as these instantly give off luxurious Dark Academia vibes! Add a leather belt to tie the look together. This outfit will be apt for cozy coffee dates!
2. Short Sleeved Shirt and Pleated Skirt
Need a bright preppy outfit for the spirit week? This all-white combo is the perfect choice, paired with pearls and pumps!
3. Shirt and Plaid Pleated Skirt
Bring in that scholar energy with this vintage-style contrasting preppy outfit! Throw in a scouts tie and chunky boots and you’re good to go!
4. Crop Top & Long Skirt Set with Blazer
A vibrant modest preppy outfit for a formal occasion! If you don’t want a matchy-matchy look, go for a contrasting blazer and shoes! This can also be a classy dinner outfit when paired with sleek jewelry!
5. Cropped Blazer, Strap Top and High Waist Trousers
If you fancy a modern yet formal prep fit, this is your go-to combo in winter! Add in a longline coat in black if the weather gets a little too chilly!
6. Tie Knot Blouse, Mini Skirt and Plaid Long Coat
A leather skirt and solid blouse combo is simply epic when you wear them in preppy colors of tan and white! Throw in a plaid coat to bring in some contrast
7. Ribbed Long Sleeved Top and Pinafore
Need a cutesy preppy outfit for a garden date? This simple combo is perfect! This outfit goes well with sleek statement jewelry, like stackable rings, and casual sneakers!
8. Long Sleeved Striped Shirt and Flared Skirt
A great outfit combo to ease into the preppy aesthetics if you’re a beginner, these stripes rarely miss! With buckle belts and ankle boots, you’re ready for a casual coffee date!
9. Crop with Blazer and Shorts
A super casual outfit that maintains the preppy aesthetics! This look is perfect for hot game days as well as other daytime events! Don’t forget to add sleek costume jewelry!
10. Cropped Knit Sweater and Shirt with Mini Skirt
This contrasting preppy outfit steers away from the traditional looks that belong to the aesthetic! With mid-calf socks and sneakers, you can add a rebellious touch to the fit!
11. Cropped Sweater, Solid Shirt and Pleated Skirt
If you have a museum date in fall season, this preppy outfit combo in gray tones is a classy option! A pair of mesh tights and fedora hats complete the look.
12. Shirt, Plaid Jacket and Skirt Co-ord
A plaid preppy combo like this one is nostalgic to the 90s Chanel couture shows! When worn with pearl accessories and buckle shoes, you have a look that screams spring bliss!
13. Cropped Shirt, Sweater Vest, Asymmetric Mini Skirt and Blazer
There’s a relaxed appeal to styling preppy outfits with untucked shirts that make them irresistible! So this fall, try on this stylish pairing with mesh tights and lace-up boots that match!
14. Solid Shirt and Pleated Mini Skirt
Keeping the preppy girl look minimal with this shirt and skirt combo, the outfit looks crazily balanced with mesh stockings and loafers having pearl detailing!
15. Solid Shirt, Mini Skirt and Fitted Long Blazer
Channel that ‘Blair Waldorf’ energy with this stellar vintage preppy look next summer! Opt for a contrast beret and ruffle socks to go with the look for a classy appeal!
16. Solid Shirt, Flared Mini Skirt and Mesh Strap Top
In the mood for styling a hot preppy look for a night out? Layer a solid shirt and skirt combo with stellar sheer tops and matching tights to nail an iconic look! A slim leather belt is another chic detail to add!
17. Solid Shirt, Pleated Skirt and Sweater Vest
A blend of monochrome garbs for a stylish fall apt preppy look, try on this combo with cowboy boots and fedora hats for that old-school country aesthetics!
18. Shirt, Pleated Skirt and Sweater
A sweater tied around your neck can transform any combination into a chic collegiate outfit! So next time you’re picking a campus fit, try on this combo with a solid tie and loafers!
19. Shirt, Strap Dress and Longline Coat
Bring back the ‘slip dress over shirt trend’ but in preppy style with this sizzling look! While the plaid coat is a good winter addition, you can try this look for the summer without the coat!
20. Cardigan, Oversized Shirt and Mini Skirt
Grab a geometric print cardigan and layer it over your preppy shirt and skirt fit for this vintage look! Accent this look with a beret and mini hoops!
21. Floral Button Down Dress
Why stick to solid preppy looks when you can have stylish floral prints like these! Throw in a beret and pearl jewelry and you’ve got an “it girl” fit!
22. Turtleneck Sweater, Loose Fit Jacket and Tapered Pants
Need a preppy look that’s a tad bit sporty? Try on this solid combo with lace-up boots and an edgy hair updo for that much-needed adventure energy!
23. Pleated Skirt and Ruffle Blouse
Add a subtle hint of femininity to your prep fits with this solid combo! Leather boots are a must-have for this one! But, you can always opt for Oxford shoes in the summer as well!
24. Loose Fit Shirt, Sweater, Mini Skirt and Longline Coat
The key to nailing this posh preppy look lies in sticking to black and tan palette! You can accent this subtle preppy outfit with mesh tights, leather belts, and ankle boots!
25. Long Sleeved Crop Top, Sweater Vest and Mini Skirt
Bring in that Gen-Z energy to the traditional preppy outfits with this ensemble! Add in mesh stockings and rhinestone earrings and accessorize!
26. Blazer, Mini Skirt and Solid Shirt
A classic preppy outfit! This solid blazer and skirt combo is a smashing hit regardless of which season you plan on donning it. But, try opting for court heels rather than boots!
27. Leather Corset, Loose Fit Shirt and Shorts
Take a break from the poised look of preppy fits with an edgy ensemble like this one! With this fit, you can add mesh stockings, fedora hats, layered necklaces and more!
28. Suspenders + Trousers and Loose Fit Shirt
For some razzle dazzle in preppy rider gear, try on this stylish fit! Heavy gold accessorizing is a must-have for this one with fedora hats and ties to add as well!
29. Turtleneck Ribbed Top, Longline Coat and Slip On Dress
Looking for some intern apt preppy outfits? Dress over-top combo like this one is a great place to start! Opt for sneakers and minimal jewelry, like chin dangler earrings and anklets!
30. Loose Fit Sweater and Plaid Skirt
This combination creates an elegant preppy look perfect for a night club or party! For this one, fedora hats in tan shades and textured suede boots are good additions!
31. Turtleneck Sweater and High Waist Mini Skirt
Keep your preppy look a little on the minimal side for family dinners with this pairing! You can always add in studded leather belts and pendants to balance out the solids in the fit!
32. Loose Fit Shirt and Mini Skirt
Personalize your traditional black and white preppy outfits by adding in these trendy ties, gold hoop earrings and Chelsea boots!
