10 Unique Preppy Outfits to Style an Edgy Fashion Look

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Regarding Preppy outfits, most people envision a navy blazer, a crisp Oxford shirt, chinos, loafers, and a preppy tie – the quintessential Ivy League style.

However, the realm of Preppy fashion is much more versatile and imaginative than one might think.

Preppy styles evolved, blending cherished classic elements with trendy aesthetics from different eras and subcultures.

In this article, we’ll introduce you to 10 Preppy outfit ideas that are anything but conventional.




1. 80s Preppy

midi or maxi plaid skirt, white blouse, boots, handbag

Start your 80s Preppy style outfit with a white silk notch collar button-up blouse to reflect the decade’s sophistication.

Layer the blouse over a patchwork sweater vest, capturing the era’s affinity for including British aesthetic elements into the classic Ivy League Preppy look.

midi or maxi plaid skirt, plaid vest, white blouse, boots
80s preppy fashion: midi or maxi plaid skirt, plaid vest, white blouse, boots

Include a high waist A-line plaid midi skirt to accentuate the throwback vibe while retaining the Preppy aesthetic.

Complete the retro Preppy look with knee-high faux leather boots in a crocodile pattern, popular in 80s fashion.

White silk notch collar button-up blouse. Black and red patchwork pattern sweater vest.
High waist a-line plaid midi skirt in red and black. Knee high brown faux leather boots in crocodile pattern.




2. 90s Preppy

plaid blazer, vest, white top, plaid miniskirt, knee-high shocks

For the 90s Preppy style outfit idea, begin with a white V-neck blouse with long sleeves to set a classic and clean base.

Top it off with a plaid print crop blazer in brown, reminiscent of the decade’s plaid craze, and a pleated skirt in a similar shade, a signature piece in the 90s Preppy wardrobe.

plaid button-up blazer, plaid pleated miniskirt, button-up shirt, shoulderbag, knee-high socks, platform wedges
90s Preppy Outfit -plaid button-up blazer, plaid pleated miniskirt, button-up shirt, shoulderbag, knee-high socks, platform wedges

Slip into over-the-knee socks for that quintessential schoolgirl charm and opt for black leather lace-up shoes with chunky soles to ground the look with a touch of 90s grunge.

Finally, accessorize with a baguette-style shoulder bag, the 90s style it-bag, to showcase a sense of Preppy chic nostalgic vibe.

Plaid Print Crop Blazer & Pleated Skirt WHITE V NECK BLOUSE
Solid Over The Knee Socks Minimalist Baguette shoulderbag Bag




3. 2000s Preppy

pleated miniskirt, statement top, high heel shoes, preppy accesories

Start with a “Baby Girl” graphic tee, channeling the 2000s’ affection for playful and flirty statements.

Elevate the look with a letter rhinestone zip-up velvet hoodie for that quintessential early 2000s bling and luxe vibe.

pleated miniskirt, statement top, high heel shoes
2000s preppy fashion: pleated miniskirt, statement top, high heel shoes

Pair these with a school-style pleated mini skirt in pink, capturing the era’s penchant for Preppy charm.

Finish the ensemble with high-heeled shoes in a matching pink shade, bringing in that touch of early-millennium glamour and sass that defined the decade’s style.

Letter Rhinestone Zip Up Velvet Hoodie Solid Pleated minikirt
Crop Tank Top with Floral & Letter Graphic print Slip-on heels with point toes in pastel pink patent leather




4. Preppy Punk

white tee, plaid pleated skirt, fishnet thighs, striped socks, sneakers

Start your Preppy Punk outfit with a skeleton print tank top to bring Punk’s edgy, rebellious style to the forefront.

Layer it with a pink plaid pleated skirt to add a dash of cuteness, and playful charm, and fishnet tights to bring in the punk scene’s raw energy.

skull print tee, plaid pleated skirt, fishnet thighs, studded bracelet, striped socks, high-top sneakers
Preppy Punk Fashion: skull print tee, plaid pleated skirt, fishnet thighs, studded bracelet, striped socks, Converse high-top sneakers

Ground the outfit with Converse high-top lace sneakers in black – a classic Punk footwear choice that blends seamlessly with the Preppy style.

Accessorize with a studded decor bracelet for the perfect finishing touch that fuses the punk rock edge with a chic, Preppy flair.

Punk Skeleton Print Tank Top Kawaii Plaid Pleated Skirt
Fishnet Tights Schoolgirl Preppy Socks
Converse high top lace sneakers in black Studded Decor Bracelet




5. Preppy Goth

plaid blazer, ruffle lace blouse, pleated skirt, knee-high socks

Kick-start your Preppy Goth outfit with an eye-catching ruffle trim sleeve shirt that blends the Victorian vibe of the Gothic style with a Preppy sensibility.

Layer it with a double-breasted blazer jacket and a plaid flare skirt, and add a touch of playfulness with a pair of over-the-calf socks.

plaid blazer, ruffle blouse, pleated skirt, knee-high socks, gothic necktie
Goth Preppy Outfit: plaid blazer, ruffle blouse, pleated skirt, knee-high socks, gothic necktie

Stomp stylishly in chunky loafers in black that resonate with the Gothic’s love for rugged footwear.

Finally, adorn yourself with a Rhinestone bow tie to incorporate a touch of sparkle and drama, sealing the Preppy Goth look with flair.

Double Breasted Plaid Formal Blazer Jacket Women Ruffle Trim Casual Over The Calf Socks
Ruffle Trim Flounce Sleeve Shirt Plaid Lace-up Flare Skirt
Rhinestone Decor Bow Tie chunky loafers in black




6. Southern Preppy

souther preppy outfit ideas

Start your Southern Preppy outfit by layering a long-sleeve button-down collar blouse with a gingham pattern under a cozy white cable knit sweatshirt for a classic and charming combination.

Pair it with linen Bermuda shorts in pastel pink to embrace the Southern charm and keep the outfit airy and comfortable.

cable knit sweatshirt in white, long-sleeve button-down collar blouse with gingham pattern, round shaped sunglasses with animal pattern, linen Bermuda shorts with darts in pastel pink, soulder bag in red patent leather, ballet flats with a bow on the front in red patent leather
Southern Preppy outfit: cable knit sweatshirt in white, long-sleeve button-down collar blouse with gingham pattern, round-shaped sunglasses with animal print, linen Bermuda shorts with darts in pastel pink, shoulder bag in red patent leather, ballet flats with a bow on the front in red patent leather

Accessorize with round-shaped sunglasses featuring an animal print for a contemporary twist and a touch of boldness.

Complete the ensemble with red patent leather ballet flats with a bow on the front and a matching shoulder bag in red patent leather to inject color and polished finesse into the look.

half-sleeve button-down collar blouse with stripe pattern Rolled up button front bermuda shorts in pastel pink
10 Unique Preppy Outfits to Style an Edgy Fashion Look mini shoulderbag in red patent leather with small handler on the top and zipper
sunglasses in round shaped lens and in leopard pattern frame Pointy toes ballet flats in red with bow decor




7. Avantgarde Preppy

shoulder-padded plaid blazer, plaid skirt, shirt, plaid tie knee-high socks

Start with a checkered blazer jacket with extreme shoulder pads and a stretchy silk button-up blouse to enhance the avant-garde boldness of the jacket’s silhouette.

shoulder-padded plaid blazer, plaid skirt, shirt, plaid tie, knee-high socks
Edgy Preppy outfit: shoulder-padded plaid blazer, plaid skirt, shirt, plaid tie, knee-high socks

Add a plaid contrast lace-up skirt for a mix of texture and pattern, and wear over-the-knee socks for a preparatory school touch.

Finish the look with round-toe chunky Dr. Marten shoes for rebellious flair and a Scottish plaid pattern tie that reminds you of the style’s heritage.

check blazer jacket with extreme shoulder pads in red Stretch Silk button-up Blouse
Solid Over The Knee Socks Plaid Pattern Tie
Plaid Contrast Lace Up Skirt Round toe chunky Dr. Marten's shoes




8. Preppy Grunge

oversized knitted plaid sweatshirt, shirt, pleated miniskirt, thighs, leg warmer, hairband, flat shoes

Start your Preppy Grunge fusion outfit with an oversized button-up shirt as your base.

Layer the shirt with a shoulder-dropped sweater in a classic argyle pattern that recalls the Preppy style aesthetic roots.

oversized knitted plaid sweatshirt, shirt, pleated miniskirt, thighs, hairband, flat shoes
Grunge Preppy outfit: oversized knitted plaid sweatshirt, shirt, pleated miniskirt, thighs, hairband, flat shoes

Incorporate a pleated hem skirt for an added schoolgirl charm and a pair of ripped-apart stockings for that Grunge edge.

Complete the look with chunky flat sandals with tractor soles and a plaid bandana around the neck for flair and rebellion.

Argyle Pattern Drop Shoulder Sweater Oversized button up Shirt
plaid bandana Solid Tearable Stockings & 1pair Fishnet Tights
Solid Pleated Hem Skirt chunky flat shoes in black




9. Boho Preppy

Colorful knitted puff sleeve button-up cardigan, ruffle blouse, ruffle miniskirt, high heel sandals

Kick off your Preppy Boho outfit with a flounce sleeve ruffle blouse with flowery prints as a nod to the Bohemian style.

Complement the blouse with a floral pattern tie front cardigan for a touch of whimsy and style.

Colorful knitted puff sleeve button-up cardigan, ruffle blouse, ruffle miniskirt, high-heel sandals, boho belt
Boho Preppy outfit: Colorful knitted puff sleeve button-up cardigan, ruffle blouse, ruffle miniskirt, high-heel sandals, boho belt

Pair them with a layered ruffle lace pep-hem miniskirt and a blue gemstone decor buckle belt to capture the free-spirited essence of Boho.

Finish the ensemble with wedge platform sandals in pink, blending the sophistication of the Preppy style with Bohemian flair.

Floral Pattern Tie Front Cardigan Allover Print Flounce Sleeve Ruffle Trim Blouse
layered ruffle LACE PEP HEM miniskirt wedge platform sandals in pink




10. College Preppy

white shirt, knitted vest, pleated miniskirt, handbag

Begin your College Preppy outfit with a classic round collar button-up blouse, a timeless piece in any Preppy wardrobe.

Similar to the ‘Academia’ styles such as Dark Academia and Light Academia, Layer a thick knitwear vest over the blouse for a collegiate and cozy touch.

white shirt, knitted vest, pleated miniskirt, handbag
Preppy College outfit: white button-up shirt, knitted vest, pleated miniskirt, handbag

Add a pleated mini skirt in a checkered pattern with a brown leather buckle-up accessory, blending classic academia with modern trends.

Finalize the look with chunky loafers with tractor soles in black patent leather and a Y2K Biker shoulder bag in a croc pattern for a touch of retro chic and practicality.

round collar button-up blouse knitwear vest
Pleated mini skirt in checkered pattern and with a buckle-up accessory in brown leather. Y2K Biker Shoulder Bag




Styling Tips

  • As we conclude this delightful tour through the world of preppy outfits, it’s evident that the Preppy fashion style is anything but monotonous.
  • Whether you are a lover of vintage styles, a punk-rock enthusiast, or someone who loves the classic charm of the Southern Belle, Preppy fashion is your canvas.
  • Preppy style’s adaptable nature has blended with past eras, subcultures, and fashion trends, offering an eclectic palette of options, as showcased by the 11 outfit ideas above.
  • So, get inspired, don your plaid skirt, pump shoes, and pearls, and make a statement with your unique Preppy outfit style.
  • After all, fashion is an art form that reflects who we are, and a unique Preppy outfit is an excellent way to express yourself.

Weekly Newsletter

Keep up with the latest in fashion, beauty and style!

After years of managing hundreds of fashion brands from London's office of a global retailer, Mandy has ventured into freelancing. Connected with several fashion retailers and media platforms in the US, Australia, and the UK, Mandy uses her expertise to consult for emerging fashion brands create top-notch content as an editorial strategist for several online publications.

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